New heterocyclic compounds

Abstract

FIELD: pharmaceutical composition.SUBSTANCE: heterocyclic compound represented by Formula 1 or a pharmaceutically acceptable salt thereof, which are 15-PGDH inhibitors can be used for the prevention or treatment of diseases associated with 15-PGDH. The values of A, B, X1, X2, Y1, Y2, Y3, Y4, Z1, Z2 and Ra in Formula 1 are given in the claims. The invention also relates to a pharmaceutical composition comprising the said compound and its use for the manufacture of a medicinal product.EFFECT: prevention or treatment of a disease associated with 15-PGDH.18 cl, 39 tbl, 413 ex

Description

[0001] FIELD TO WHICH THE INVENTION RELATES

[0002] This application claims priority based on Korean Patent Application No. 10-2023-0009009, filed on January 20, 2023, the entire disclosure of which is incorporated herein by reference. The present invention relates to novel heterocyclic compounds as 15-PGDH inhibitors.

[0003] BACKGROUND TO THE INVENTION

[0004] Prostaglandins are physiologically active substances synthesized in the body, widely distributed in organs and body fluids, and performing physiological functions in extremely small quantities. Prostaglandins are derivatives of fatty acids consisting of 20 carbon atoms, with a basic prostanoic acid skeleton and a 5-membered ring at the center of the molecular structure. They are divided into groups A through J according to the formula of the 5-membered ring, and into series 1 through 3 according to the number of double bonds in the two side chains. They are widely present in animal tissues and are known to be rapidly metabolized after synthesis from polyunsaturated fatty acids.These prostaglandins can stimulate smooth muscle contraction depending on their shape, and in some animals they lower or raise blood pressure, decrease or increase blood clotting, and are also known to promote membrane ion transport, stimulate inflammation, and suppress cardiovascular disease and viral infections.

[0005] 15-PGDH (15-hydroxyprostaglandin dehydrogenase) uses active prostaglandins such as PGD2, PGE1, PGE2, PGF2α and PGI2 as substrates and is involved in their inactivation, such as converting to 15-keto-PGE2, which catalyzes the oxidation reaction of the hydroxyl group at the 15 position of PGE2.

[0006] Receptors corresponding to 15-PGDH substrates are widely distributed with various expression sites in the body and are known to be involved in various physiological functions of the body. For example, 15-PGDH substrates include those with antifibrotic action, anti-inflammatory action, blood circulation-improving action, proliferation-promoting action, stem cell growth-promoting action, smooth muscle contractile / relaxant action, immunosuppressive action, and action on bone metabolism. Therefore, 15-PGDH inhibitors can be effectively used for the treatment or prevention of diseases such as fibrosis [pulmonary fibrosis (e.g., idiopathic pulmonary fibrosis), liver fibrosis, renal fibrosis, myocardial fibrosis, scleroderma, myelofibrosis, etc.], inflammatory diseases [chronic obstructive pulmonary disease (COPD), acute lung injury, sepsis, exacerbation of asthma and lung diseases, inflammatory bowel diseases (ulcerative colitis, Crohn's disease, etc.), peptic ulcer (e.g., NSAID-induced ulcer), autoinflammatory diseases (e.g., Behcet's disease), vasculitis syndrome, acute liver injury, acute kidney injury, non-alcoholic fatty liver disease (NAFLD), atopic dermatitis, psoriasis, interstitial cystitis, prostatitis syndrome (e.g., chronic prostatitis / chronic pelvic pain syndrome)], circulatory system diseases [pulmonary hypertension, angina pectoris, myocardial infarction, heart failure, ischemic heart disease, chronic kidney disease, renal failure, stroke, peripheral circulatory disorder, etc.], wounds [diabetic ulcer, laceration, pressure ulcer, acute mucosal injury including Stevens-Johnson syndrome, cancer chemotherapy, immunotherapy or radiotherapy, mucosal injury (mucositis or stomatitis) associated with graft-versus-host disease, etc.], autoimmune diseases [multiple sclerosis, rheumatoid arthritis, etc.], graft-versus-host disease (GVHD), hair loss, osteoporosis, ear diseases [hearing loss, tinnitus, dizziness, balance disorder, etc.], ophthalmological diseases [glaucoma, dry eye syndrome, etc.], diabetes, underactive bladder, neutropenia, stimulation of engraftment in stem cell and bone marrow or organ transplantation, neurogenesis and neuronal cell death [mental disorders, nerve injury, neurotoxic disorder, neuropathic pain, neurodegeneration], muscle regeneration [muscular dystrophy, muscle injury] and cervical ripening.

[0007] DETAILED DESCRIPTION OF THE INVENTION

[0008] PURPOSE OF THE INVENTION

[0009] The problem to be solved by the present invention is to provide a new 15-PGDH inhibitory compound having a structure that exhibits excellent 15-PGDH inhibitory activity.

[0010] Furthermore, the problem to be solved by the present invention is to provide a pharmaceutical composition for the prevention or treatment of diseases associated with 15-PGDH, which comprises a 15-PGDH inhibitory compound having a new structure.

[0011] Furthermore, the problem to be solved by the present invention is to provide a method for preventing or treating a disease associated with 15-PGDH, which comprises administering to a subject in need thereof a therapeutically effective amount of a 15-PGDH inhibitory compound having a new structure.

[0012] Furthermore, the problem to be solved by the present invention is to provide the use of a new 15-PGDH inhibitory compound having a new structure as an effective ingredient for the manufacture of a medicament for the prevention or treatment of a disease associated with 15-PGDH.

[0013] The problems to be solved by the present invention are not limited to the problems listed above, and a person having ordinary skill in the technical field to which the present invention pertains can clearly understand other technical problems not listed above from the description below.

[0014] PROBLEM SOLUTIONS

[0015] In order to solve the above problem, according to one aspect of the present invention, there is provided a heterocyclic compound represented by the following Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof:

[0016] <Formula 1>

[0017]

[0018] where

[0019] The fused bicyclic ring is formed from ring A and ring B,

[0020] X1, Y1, Y2, Y3 and Y4 independently represent CH or N,

[0021] X2 represents CH, N or NH,

[0022] Z1 and Z2 represent C or N,

[0023] at least one of X1, X2, Y1, Y2, Y3, Y4, Z1 and Z2 is N or NH

[0024] R a represents H, C 1-6 straight or branched chain alkyl substituted with R a-1 , or C(O)R a-1 ,

[0025] R a-1 represents C 1-6straight or branched chain alkyl, C 3-8 cycloalkyl, hydroxy, R s or R u , and R a-1 optionally substituted by one or more independent R a-2 ,

[0026] R a-2 represents C 1-6 straight or branched chain alkyl, halogen, C 1-4 haloalkyl,

[0027] X1 optionally substituted with R b , where R b is amino, or C(O)R s ,

[0028] Y1 optionally substituted with R 1 , R 1 represents R f ,

[0029] Y2 optionally substituted with R 2 ,

[0030] R 2 represents C 1-6 straight or branched chain alkyl, halogen, C 5-12 aryl with 1-2 rings, R u or R f , and R 2 optionally substituted by one or more independent R 2-1 ,

[0031] R 2-1 represents C 1-4 alkoxy, halogen or hydroxy,

[0032] Y3optionally substituted with R 3 ,

[0033] R 3 represents C 5-7 aryl, R u or R f , and R 3 optionally substituted by one or more independent R 3-1 ,

[0034] R 3-1 represents C 1-4 alkoxy, halogen, hydroxy or cyano,

[0035] Y4 optionally substituted with R 4 or -LR 4 ,

[0036] L is -NH(CH2) m -, -NHC(O)-, -NHSO2- or -S-, m is an integer from 0 to 3,

[0037] R 4 represents C 5-12 aryl with 1-2 rings, R u , R s or R f , and R 4 optionally substituted by one or more independent Q,

[0038] Q represents C 1-6 straight or branched chain alkyl, halogen, hydroxy, C 1-4 haloalkyl, C 1-4 alkoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR5 , CH2R 5 , NR 5 R 6 , C(O)R 5 , C(O)OR 5 , C(O)NR 5 R 6 , NHC(O)(CH2) p R 5 , NHC(O)CH2OR 5 , NHC(O)CH2NR 5 R 6 , NHCH2CH2R 5 , NR 5 C(O)R 6 , R u or R s , p is an integer from 0 to 3, and Q is optionally substituted by one or more independent R 7 ,

[0039] R 5 and R 6 independently represent H, C 1-6 straight or branched chain alkyl, C 3-8 cycloalkyl, C 1-4 alkoxy, amino, sulfonyl, C 5-7 aryl, arylalkyl, R u or R s ,

[0040] R 7 represents C 1-6 straight or branched chain alkyl, C 3-8 cycloalkyl, halogen, C 1-4 haloalkyl, hydroxy, C 1-4 alkoxy, hydroxyalkyl, cyano, amino, alkylamino, C 1-6alkyl carboxylate, nitro, R u , C 1-4 alkyl substituted with R u , or R s , and the relationship between Q and R 7 represents a single bond or a double bond,

[0041] R s is a 4- to 10-membered saturated heterocycloalkyl ring with 1-2 rings having from 1 to 3 heteroatoms selected from N, O and S,

[0042] R u is a 5- to 7-membered unsaturated heterocycloalkyl ring having from 1 to 4 heteroatoms selected from N, O and S,

[0043] R f is a fused bicyclic ring in which a 5-7-membered saturated or unsaturated heterocycloalkyl ring having 1-2 heteroatoms selected from N, O and S is fused with an aryl ring or a 5-7-membered heteroaryl ring having 1-2 N atoms,

[0044] R s , R u and R f independently optionally substituted with one or two oxo (O) or thioxo (S) groups.

[0045] According to another aspect of the present invention, there is provided a pharmaceutical composition for the prevention or treatment of a disease associated with 15-PGDH, comprising as an active ingredient a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

[0046] According to another aspect of the present invention, there is provided a method for preventing or treating a disease associated with 15-PGDH, comprising administering to a subject in need thereof a therapeutically effective amount of a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

[0047] According to another aspect of the present invention, there is provided the use of a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, as an effective ingredient for the manufacture of a medicament for the prevention or treatment of a disease associated with 15-PGDH.

[0048] According to another aspect of the present invention, there is provided a pharmaceutical composition comprising a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive.

[0049] EFFECTS OF INVENTION

[0050] It was confirmed that the novel heterocyclic compound of the present invention exhibits excellent 15-PGDH-inhibiting activity, and thus it was found that it can be used for the prevention or treatment of diseases associated with 15-PGDH.

[0051] Therefore, the novel heterocyclic compounds of the present invention can be effectively used for the prevention or treatment of diseases associated with 15-PGDH in the medical and pharmaceutical fields.

[0052] The effects of the present invention are not limited to the effects described above, and should be understood to include all effects that can be deduced from the composition of the invention described in the description of the present invention or in the claims.

[0053] BEST MODE FOR CARRYING OUT THE INVENTION

[0054] The present invention provides a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof:

[0055] <Formula 1>

[0056]

[0057] where

[0058] The fused bicyclic ring is formed from ring A and ring B,

[0059] X1, Y1, Y2, Y3 and Y4 independently represent CH or N,

[0060] X2 represents CH, N or NH,

[0061] Z1 and Z2 represent C or N,

[0062] at least one of X1, X2, Y1, Y2, Y3, Y4, Z1 and Z2 is N or NH

[0063] R a represents H, C 1-6 straight or branched chain alkyl substituted with R a-1 , or C(O)R a-1 ,

[0064] R a-1 represents C 1-6 straight or branched chain alkyl, C 3-8 cycloalkyl, hydroxy, R s or R u , and R a-1 optionally substituted by one or more independent R a-2 ,

[0065] R a-2 represents C 1-6 straight or branched chain alkyl, halogen, C 1-4 haloalkyl,

[0066] X1 optionally substituted with R b , where R b is amino, or C(O)R s ,

[0067] Y1 optionally substituted with R 1 , R 1 represents R f ,

[0068] Y2 optionally substituted with R 2 ,

[0069] R 2 represents C 1-6 straight or branched chain alkyl, halogen, C 5-12 aryl with 1-2 rings, R u or R f , and R 2 optionally substituted by one or more independent R 2-1 ,

[0070] R 2-1 represents C 1-4 alkoxy, halogen or hydroxy,

[0071] Y3 optionally substituted with R 3 ,

[0072] R 3 represents C 5-7 aryl, R u or R f , and R 3 optionally substituted by one or more independent R 3-1 ,

[0073] R 3-1 represents C 1-4 alkoxy, halogen, hydroxy or cyano,

[0074] Y4 optionally substituted with R 4 or -LR 4 ,

[0075] L is -NH(CH2) m -, -NHC(O)-, -NHSO2- or -S-, m is an integer from 0 to 3,

[0076] R 4 represents C 5-12 aryl with 1-2 rings, R u , R s or R f , and R 4 optionally substituted by one or more independent Q,

[0077] Q represents C 1-6 straight or branched chain alkyl, halogen, hydroxy, C 1-4 haloalkyl, C 1-4 alkoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR 5 , CH2R 5 , NR 5 R 6 , C(O)R 5 , C(O)OR 5 , C(O)NR 5 R 6 , NHC(O)(CH2) p R 5 , NHC(O)CH2OR 5 , NHC(O)CH2NR 5 R 6 , NHCH2CH2R 5 , NR 5 C(O)R 6 , R u or R s , p is an integer from 0 to 3, and Q is optionally substituted by one or more independent R7 ,

[0078] R 5 and R 6 independently represent H, C 1-6 straight or branched chain alkyl, C 3-8 cycloalkyl, C 1-4 alkoxy, amino, sulfonyl, C 5-7 aryl, arylalkyl, R u or R s ,

[0079] R 7 represents C 1-6 straight or branched chain alkyl, C 3-8 cycloalkyl, halogen, C 1-4 haloalkyl, hydroxy, C 1-4 alkoxy, hydroxyalkyl, cyano, amino, alkylamino, C 1-6 alkyl carboxylate, nitro, R u , C 1-4 alkyl substituted with R u , or R s , and the relationship between Q and R 7 represents a single bond or a double bond,

[0080] R s is a 4- to 10-membered saturated heterocycloalkyl ring with 1-2 rings having from 1 to 3 heteroatoms selected from N, O and S,

[0081] R uis a 5- to 7-membered unsaturated heterocycloalkyl ring having from 1 to 4 heteroatoms selected from N, O and S,

[0082] R f is a fused bicyclic ring in which a 5-7-membered saturated or unsaturated heterocycloalkyl ring having 1-2 heteroatoms selected from N, O and S is fused with an aryl ring or a 5-7-membered heteroaryl ring having 1-2 N atoms,

[0083] R s , R u and R f independently optionally substituted with one or two oxo (O)- or thioxo (S) groups.

[0084] In one embodiment, ring A may be pyrrole, pyrazole, imidazole, or triazole, and ring B may be benzene, pyridine, pyrimidine, or triazine.

[0085] In one embodiment, the fused bicyclic ring consisting of ring A and ring B may be indole, indazole, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, pyrazolopyridine, imidazopyridine, or triazolopyridine. More specifically, the fused bicyclic ring consisting of ring A and ring B may be selected from the group consisting of the following:

[0086]

[0087] In one embodiment, R a can be H, propyl, C(O)R a-1 , R a-1 may be methyl, butyl, cyclohexyl, hydroxy, piperidinyl, azaspiroheptanyl, azaspirooctanyl, azaspirononanyl, azabicycloheptanyl, azabicyclooctanyl, azabicyclononanyl, or tetrahydropyridinyl, and R a-2 may be methyl, ethyl, propyl, isopropyl, fluorine, or trifluoromethyl.

[0088] In one embodiment, R bmay be amino or piperidinyl carbonyl.

[0089] In one embodiment, R 1 may be benzodioxolyl.

[0090] In one embodiment, R 2 may be methyl, fluorine, phenyl, naphthyl (naphthalenyl), furanyl, pyridinyl, isoindolinone, benzodioxolyl, dihydrobenzodioxinyl, benzofuranyl, or indazolyl, and R 2-1 may be methoxy, chlorine, fluorine or hydroxy.

[0091] In one embodiment, R 3 may be phenyl, pyridinyl, or benzodioxolyl, and R 3-1 may be methoxy, chlorine, hydroxy or cyano.

[0092] In one embodiment, L may be -NH-, -NHCH2-, -NH(CH2)2-, -NHC(O)-, -NHSO2-, or -S-.

[0093] In one embodiment, R 4may be phenyl, naphthyl (naphthalenyl), furanyl, pyrazolyl, dihydropyridinyl, pyridinyl, pyrimidinyl, pyridinone, pyrimidinone, isoxazolyl, piperidinyl, benzodioxolyl, isoindolinone, dihydroisoquinolinone, benzofuranyl, benzothiophenyl, indolyl, indazolyl, quinolinyl, quinolinone, isoquinolinone, dihydropyrrolopyridinone, benzoisoxazolone, dihydronaphthyridinone, benzoxazolyl, benzoisoxazolyl, triazolopyridinone, phthalazinone, quinazolinone, or pyridopyrimidinone.

[0094] In one embodiment, Q may be methyl, propyl, isopropyl, fluoro, chloro, bromo, hydroxy, trifluoromethyl, methoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR 5 , CH2R 5 , NR 5 R 6 , C(O)R 5 , C(O)OR 5 , C(O)NR 5 R 6 , NHC(O)R 5 , NHC(O)CH2R 5 , NHC(O)(CH2)2R 5 , NHC(O)CH2OR 5 , NHC(O)CH2NR 5 R 6 , NHCH2CH2R 5 , NR 5 C(O)R6 , tetrazolyl, oxadiazolyl, oxadiazolyl, furyl, thienyl, imidazolyl, pyrazolyl, isoxazolyl, thiazolyl, oxo-thiadiazolyl, thioxo-oxadiazolyl, pyridinyl, pyrimidinyl, azetidinyl, oxazolidinone, piperidinyl, piperazinyl, morpholino, azaspiroheptanyl, azaspirooctanyl, azaspirononanyl, azabicycloheptanyl or azabicyclooctanyl, R 5 may be H, methyl, ethyl, butyl, cyclopropyl, cyclohexane, methoxy, amino, phenyl, benzyl, imidazolyl, oxadiazolyl, oxadiazolone, pyridinyl, pyrimidinyl, azetidinyl, piperidinyl, piperidinone, piperazinyl, morpholino, thiazolidinedione, piperazinone, piperazinedione, azaspiroheptanyl or azaspirononanyl, and R 6 may be H, methyl, ethyl, propyl, isopropyl, sulfonyl, pyrazolyl, pyridinyl, pyridazinyl, azetidinyl, or piperidinyl.

[0095] In one embodiment, R 7may be methyl, propyl, isopropyl, cyclopropyl, fluoro, chloro, difluoromethyl, trifluoromethyl, hydroxy, methoxy, hydroxymethyl, cyano, amino, dimethylamino, methyl carboxylate, tert-butyl carboxylate, nitro, isoxazolyl, thiazolyl, pyridinyl, or oxadiazolylmethyl.

[0096] In this description, the following definitions are used when defining compounds of Formula 1 unless otherwise specified.

[0097] The term "alkyl" refers to a hydrocarbon group with a straight or branched chain, preferably C1-C 10 alkyl. Examples of alkyl include, but are not limited to, methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, n-pentyl, iso-pentyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, n-octyl, n-nonyl, indecyl, etc.

[0098] The term "cycloalkyl" refers to a partially or fully saturated hydrocarbon with one or fused ring, preferably C3-C 10-cycloalkyl. Examples of cycloalkyl include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclohexenyl.

[0099] The term "hydroxy" or "hydroxyl" is defined as -OH, and the term "alkoxy" means alkyloxy, a radical in which the hydrogen atom of the hydroxyl group is replaced by 1 to 10 alkyl groups, unless otherwise specified.

[0100] The term "halogen" refers to fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

[0101] The terms “haloalkyl” and “haloalkoxy” mean alkyl or alkoxy substituted by one or more halogen atoms.

[0102] The term "heteroatom" means N, O, or S.

[0103] The term "aryl" means an aromatic hydrocarbon, including polycyclic aromatic ring systems in which a carbocyclic aromatic ring or a heteroaryl ring is fused to one or more other rings. Preferably, it is C 5-12 aryl, more preferably C 5-10aryl. For example, aryl includes, but is not limited to, phenyl, naphthyl, tetrahydronaphthyl, and the like. Also included are groups in which a heteroaryl ring is fused to a cycloalkyl or non-aromatic heterocyclic ring such as indanyl or tetrahydrobenzopyranyl.

[0104] The term "heteroaryl" or "aromatic heterocycle" means a 3- to 12-membered, more preferably 5- to 10-membered aromatic hydrocarbon group having one or more heteroatoms selected from N, O and S as a ring atom and forming a single or fused ring which may be fused with benzo or C 3-8cycloalkyl. For example, heteroaryl includes, but is not limited to, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, pyridyl, pyrazinyl, pyrimidyl, pyridazinyl, triazinyl, oxadiazolyl, isoxadiazolyl, tetrazolyl, indolyl, indazolyl, isoxazolyl, oxazolyl, thiazolyl, isothiazolyl, furanyl, benzofuranyl, thiophenyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, and the like.

[0105] Representative examples of heterocyclic compounds according to the present invention are as follows:

[0106] [1]7-phenylpyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0107] [2] (7-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0108] [3] methyl 3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate,

[0109] [4] (7-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0110] [5] (7-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0111] [6] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0112] [7] (7-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0113] [8] (7-(2-chloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0114] [9] (7-(5-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0115]

[10] 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoic acid,

[0116]

[11] methyl 4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate,

[0117]

[12] (7-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0118]

[13] (7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0119]

[14] (7-(4-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0120]

[15] 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0121]

[16] (7-(6-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0122]

[17] (7-(6-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0123]

[18] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinonitrile,

[0124]

[19] (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0125]

[20] (7-(4-methoxy-3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0126]

[21] (7-(3-chloro-4-hydroxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone],

[0127]

[22] 2-fluoro-4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0128]

[23] 2-(Dimethylamino)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0129]

[24] (7-(3,4-dimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0130]

[25] (7-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0131]

[26] (7-(3-(morpholine-4-carbonyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0132]

[27] N-methyl-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0133]

[28] N-isopropyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0134]

[29] azetidin-1-yl(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone,

[0135]

[30] N-(2-methoxyethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0136]

[31] N-(2-(dimethylamino)ethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0137]

[32] N-(cyclopropylmethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0138]

[33] N-(1-methylpiperidin-4-yl)-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0139]

[34] piperazin-1-yl(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone,

[0140]

[35] tert-butyl 4-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoyl)piperazine-1-carboxylate,

[0141]

[36] N-(2-cyanoethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0142]

[37] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide,

[0143]

[38] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide,

[0144]

[39] (7-(5-(morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0145]

[40] N-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0146]

[41] azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[0147]

[42] (3-hydroxyazetidin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[0148]

[43] (7-(5-(2-azaspiro[3.3]heptan-2-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0149]

[44] (3,3-Difluoroazetidin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[0150]

[45] N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0151]

[46] N-(cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0152]

[47] N-(1-methylpiperidin-4-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0153]

[48] piperazin-1-yl(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[0154]

[49] (4-methylpiperazin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[0155]

[50] (4-isopropylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[0156]

[51] N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0157]

[52] N-(cyanomethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0158]

[53] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)nicotinamide,

[0159]

[54] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)nicotinamide,

[0160]

[55] N-(isoxazol-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0161]

[56] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridazin-4-yl)nicotinamide,

[0162]

[57] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(thiazol-5-ylmethyl)nicotinamide,

[0163]

[58] N-methyl-4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0164]

[59] N,N-dimethyl-4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0165]

[60] N-isopropyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0166]

[61] azetidin-1-yl(4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone,

[0167]

[62] N-(2-methoxyethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0168]

[63] N-(2-(dimethylamino)ethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0169]

[64] N-(cyclopropylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0170]

[65] N-(1-methylpiperidin-4-yl)-4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0171]

[66] piperazin-1-yl(4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone,

[0172]

[67] (4-methylpiperazin-1-yl)(4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone,

[0173]

[68] (4-isopropylpiperazin-1-yl)(4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone,

[0174]

[69] N-(2-cyanoethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0175]

[70] N-(cyanomethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0176]

[71] 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide,

[0177]

[72] 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide,

[0178]

[73] N-(isoxazol-3-ylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0179]

[74] (7-(6-(morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0180]

[75] N-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0181]

[76] N-isopropyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0182]

[77] azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone,

[0183]

[78] N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0184]

[79] N-(2-(dimethylamino)ethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0185]

[80] N-(cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0186]

[81] N-(1-methylpiperidin-4-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0187]

[82] piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone,

[0188]

[83] (4-methylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone,

[0189]

[84] (4-isopropylpiperazin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone,

[0190]

[85] N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0191]

[86] N-(cyanomethyl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0192]

[87] 5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)picolinamide,

[0193]

[88] 5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)picolinamide,

[0194]

[89] N-(isoxazol-3-ylmethyl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide,

[0195]

[90] N-(2-cyanoethyl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)furan-2-carboxamide,

[0196]

[91] 3-methoxy-N-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide,

[0197]

[92] 1-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)urea,

[0198]

[93] 1-methyl-N-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidin-4-carboxamide,

[0199]

[94] N-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropanecarboxamide,

[0200]

[95] N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide,

[0201]

[96] N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide,

[0202]

[97] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)acetamide,

[0203]

[98] 3-methoxy-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide,

[0204]

[99] 1-Methyl-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide,

[0205]

[100] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropanecarboxamide,

[0206]

[101] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide,

[0207]

[102] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide,

[0208]

[103] 3-Methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)propanamide,

[0209]

[104] 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide,

[0210]

[105] 2-oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)piperidin-4-carboxamide,

[0211]

[106] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide,

[0212]

[107] (7-(6-((3-methoxypropyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0213]

[108] (7-(6-morpholinopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0214]

[109] (7-(6-(isopropylamino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0215]

[110] piperidin-1-yl(7-(6-(piperidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0216]

[111] (7-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0217]

[112] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanesulfonamide,

[0218]

[113] (7-(3-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0219]

[114] (7-(4-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0220]

[115] 3-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0221]

[116] 3-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0222]

[117] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-1,2,4-oxadiazol-5(4H)-one,

[0223]

[118] (7-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0224]

[119] (Z)-5-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzylidene)thiazolidine-2,4-dione,

[0225]

[120] tert-butyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate,

[0226]

[121] (7-(benzo[d][1,3]dioxol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0227]

[122] (7-(benzofuran-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0228]

[123] (7-(benzofuran-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0229]

[124] (7-(benzo[b]thiophen-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0230]

[125] (7-(1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0231]

[126] (7-(1H-indol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0232]

[127] (7-(benzofuran-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0233]

[128] (7-(naphthalene-1-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0234]

[129] (7-(naphthalene-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0235]

[130] piperidin-1-yl(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0236]

[131] 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0237]

[132] 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0238]

[133] 2-isopropyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0239]

[134] 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one,

[0240]

[135] 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one,

[0241]

[136] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0242]

[137] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0243]

[138] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one,

[0244]

[139] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one,

[0245]

[140] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0246]

[141] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0247]

[142] 2-isopropyl-6-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0248]

[143] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0249]

[144] 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0250]

[145] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinolin-2(1H)-one,

[0251]

[146] 4-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)benzonitrile,

[0252]

[147] 3-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)pyridin-2(1H)-one,

[0253]

[148] piperidin-1-yl(7-((pyrimidin-2-ylmethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0254]

[149] piperidin-1-yl(7-((2-(pyridin-4-yl)ethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0255]

[150] (7-((1-methylpiperidin-4-yl)amino)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0256]

[151] 1-(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)pentan-1-one,

[0257]

[152] 4-(3-acetylpyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0258]

[153] 4-(3-(2-hydroxypropan-2-yl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0259]

[154] 7-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0260]

[155] 6-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0261]

[156] 4-(3-(4-fluoropiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0262]

[157] (4-fluoropiperidin-1-yl)(7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0263]

[158] cyclohexyl(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone,

[0264]

[159] 7-(2-amino-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0265]

[160] 7-(2-amino-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one,

[0266]

[161] (7-(3-chlorophenyl)-1H-indazol-3-yl)(piperidin-1-yl)methanone,

[0267]

[162] (8-(3-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0268]

[163] (8-(4-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0269]

[164] (8-(4-aminophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0270]

[165] (8-(3-chlorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0271]

[166] (8-(2-chloropyridin-4-yl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0272]

[167] (8-(3-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0273]

[168] (7-(4-methoxyphenyl)-[1,2,3]triazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0274]

[169] (7-(3-chlorophenyl)-1H-indol-3-yl)(piperidin-1-yl)methanone,

[0275]

[170] (6-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0276]

[171] (6-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0277]

[172] (6-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0278]

[173] (5-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0279]

[174] (4-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-c]pyridin-2-yl)(piperidin-1-yl)methanone,

[0280]

[175] (4-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[2,3-c]pyridin-2-yl)(piperidin-1-yl)methanone,

[0281]

[176] (4-(benzo[d][1,3]dioxol-5-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl)(piperidin-1-yl)methanone,

[0282]

[177] (4-(benzo[d][1,3]dioxol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)(piperidin-1-yl)methanone,

[0283]

[178] (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0284]

[179] (5-(4-methoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0285]

[180] (5-(4-chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0286]

[181] (5-(3,4-dimethoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0287]

[182] (5-(4-fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0288]

[183] ​​(5-(furan-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0289]

[184] piperidin-1-yl(5-(pyridin-4-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)methanone,

[0290]

[185] (5-(3-chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0291]

[186] (5-(3-chloro-4-hydroxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0292]

[187] (2-(benzo[d][1,3]dioxol-5-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)(piperidin-1-yl)methanone,

[0293]

[188] (5-(benzofuran-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0294]

[189] (5-(naphthalen-2-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0295]

[190] (5-(1H-indazol-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0296]

[191] 2-(2-(piperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)isoindolin-1-one,

[0297]

[192] (3-fluoroazetidin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[0298]

[193] N-(1-methyl-1H-pyrazol-3-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0299]

[194] (7-((3-methoxyphenyl)thio)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0300]

[195] 3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one,

[0301]

[196] 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide,

[0302]

[197] 3-methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)propenamide,

[0303]

[198] 2-oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)piperidin-4-carboxamide,

[0304]

[199] 6-methyl-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one,

[0305]

[200] N-(azetidin-3-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0306]

[201] N-methylsulfonyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-3-carboxamide,

[0307]

[202] N-(1-methylazetidin-3-yl)-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide,

[0308]

[203] 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazin-2-one,

[0309]

[204] 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-3-carbonyl]piperazine-2,6-dione,

[0310]

[205] 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carbonitrile,

[0311]

[206] (7-(6-(azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0312]

[207] 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-4(3H)-one,

[0313]

[208] (7-(6-(3-fluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0314]

[209] (7-(6-(3,3-difluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0315]

[210] (7-(6-(3-hydroxyazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0316]

[211] 7-[[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-3,4-dihydro-2H-isoquinoline-1-one,

[0317]

[212] 6-[[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]isoindoline-1-one,

[0318]

[213] (3-fluoroazetidine-1-yl)-[5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone,

[0319]

[214] 2-azaspiro[3.3]heptane-2-yl-[5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone,

[0320]

[215] (7-(6-(2-azabicyclo[2.2.1]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0321]

[216] (7-(6-(2-azabicyclo[2.2.2]octane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0322]

[217] -(6-(7-azabicyclo[2.2.1]heptane-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0323]

[218] (7-(6-(3-(dimethylamino)azetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0324]

[219] methyl 1-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)azetidine-3-carboxylate,

[0325]

[220] (7-(6-(2-azaspiro[3.3]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0326]

[221] (7-(6-(3-(hydroxymethyl)azetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0327]

[222] (7-(6-(7-azaspiro[3.5]nonan-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0328]

[223] (7-(6-(6-azaspiro[3.4]octane-6-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0329]

[224] 7-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazine-1(2H)-one,

[0330]

[225] (6-hydroxy-2-azaspiro[3.3]heptane-2-yl)-[5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone,

[0331]

[226] 2-oxa-7-azaspiro[3.5]nonan-7-yl-[5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone,

[0332]

[227] (2-azabicyclo[2.2.1]heptan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone,

[0333]

[228] (2-azabicyclo[2.2.2]octan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone,

[0334]

[229] (7-azabicyclo[2.2.1]heptan-7-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone,

[0335]

[230] (3-hydroxyiminoazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone,

[0336]

[231] 6-(3-(4-fluoropiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methylisoindolin-1-one,

[0337]

[232] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one,

[0338]

[233] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1(2H)-one,

[0339]

[234] 6-(3-(4,4-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0340]

[235] 4-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-1H-pyrimidin-6-one,

[0341]

[236] 3-methyl-6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]pyrimidin-4-one,

[0342]

[237] (3,3-difluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone,

[0343]

[238] [7-[(4-chlorophenyl)methylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0344]

[239] 4-chloro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzamide,

[0345]

[240] 1,3,5-trimethyl-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrazole-4-sulfonamide,

[0346]

[241] 5-fluoro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-3-carboxamide,

[0347]

[242] [7-[2-(4-chlorophenyl)ethylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0348]

[243] 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid,

[0349]

[244] methyl 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylate,

[0350]

[245] 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one,

[0351]

[246] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one,

[0352]

[247] 3-[3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-4H-1,2,4-oxadiazol-5-one,

[0353]

[248] [7-[6-(azetidine-1-carbonyl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0354]

[249] [7-[5-fluoro-6-(morpholine-4-carbonyl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0355]

[250] 3-fluoro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-2-carboxamide,

[0356]

[251] 3-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one,

[0357]

[252] 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one,

[0358]

[253] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzaldehyde oxime,

[0359]

[254] 2-Fluoro-5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile,

[0360]

[255] 3-Methyl-6-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[2,3-d]pyrimidin-4(3H)-one,

[0361]

[256] 3-Methyl-7-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[3,2-d]pyrimidin-4(3H)-one,

[0362]

[257] (7-(2-(3-fluoroazetidin-1-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0363]

[258] 3-chloro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-2-carboxylic acid,

[0364]

[259] [7-(3-amino-1,2-benzoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0365]

[260] [7-(3-amino-1H-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0366]

[261] [7-(3-amino-1-methyl-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0367]

[262] 3-chloro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide,

[0368]

[263] [7-[5-fluoro-6-(5-methyl-1,2,4-oxadiazol-3-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0369]

[264] (7-(2-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0370]

[265] (7-(5-bromo-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0371]

[266] (7-(2,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0372]

[267] (7-(2-chloropyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0373]

[268] 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzo[d]isoxazol-3(2H)-one,

[0374]

[269] (7-(3-methoxybenzo[d]isoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0375]

[270] 2-(dimethylamino)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinonitrile,

[0376]

[271] (7-(6-fluoropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0377]

[272] (7-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0378]

[273] (7-(2,6-difluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0379]

[274] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide,

[0380]

[275] 3-[2-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one,

[0381]

[276] [7-[4-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0382]

[277] [7-[2-(azetidine-1-carbonyl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0383]

[278] N-(2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide,

[0384]

[279] (7-(3-chloro-5-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0385]

[280] 5,6-dimethyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one,

[0386]

[281] (7-(6-chloro-5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0387]

[282] (7-(2,6-dichloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0388]

[283] (7-(5-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0389]

[284] (7-(5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0390]

[285] 3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile,

[0391]

[286] [7-[6-(azetidine-1-carbonyl)-5-chloro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0392]

[287] N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide,

[0393]

[288] (7-(5,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0394]

[289] (7-(5-chloro-6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0395]

[290] 2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0396]

[291] 3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0397]

[292] (7-(4-bromophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0398]

[293] 5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidine-2-carbonitrile,

[0399]

[294] [7-(2-hydroxypyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0400]

[295] 3-[3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one,

[0401]

[296] [7-[2-fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0402]

[297] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1,2,4-oxadiazol-5(4H)-one,

[0403]

[298] (7-(5-chloro-2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0404]

[299] 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0405]

[300] [7-[4-(2-methylpyrazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0406]

[301] N-(3-chloro-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide,

[0407]

[302] [7-[4-(3-furyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0408]

[303] [7-[3-fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0409]

[304] 3-[2-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one,

[0410]

[305] 5-[4-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carbonitrile,

[0411]

[306] [7-[4-(2-hydroxypyrimidine-5-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0412]

[307] 5-[4-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carboxamide,

[0413]

[308] 3-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidine-2-yl)oxazolidin-2-one,

[0414]

[309] [7-(3-amino-1H-indazole-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0415]

[310] [7-(3-amino-1-methyl-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0416]

[311] N-(3-chloro-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide,

[0417]

[312] 3-nitro-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0418]

[313] (7-(6-bromopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0419]

[314] (7-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0420]

[315] (7-(6-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0421]

[316] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0422]

[317] [7-[2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0423]

[318] (7-(5-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0424]

[319] (7-(5-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0425]

[320] [7-(3-amino-1,2-benzoxazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0426]

[321] 3-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidin-2-yl]-4H-1,2,4-oxadiazol-5-one,

[0427]

[322] (7-(3-fluoro-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0428]

[323] 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0429]

[324] [7-[4-(3,5-dimethylisoxazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0430]

[325] (7-(2-fluoro-5-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0431]

[326] N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide,

[0432]

[327] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyridin-3-yl)acetamide,

[0433]

[328] (7-(3,5-difluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0434]

[329] 3-(3-nitro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0435]

[330] (7-(3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0436]

[331] 3-(2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0437]

[332] piperidin-1-yl(7-(6-((2-(pyridin-3-yl)ethyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0438]

[333] 1,2-dimethyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1H-imidazol-5-carboxamide,

[0439]

[334] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)pyrimidin-5-carboxamide,

[0440]

[335] 5-fluoro-N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide,

[0441]

[336] (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methylpiperidin-1-yl)methanone,

[0442]

[337] (3-ethylpiperidin-1-yl)(7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0443]

[338] (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-(trifluoromethyl)piperidin-1-yl)methanone,

[0444]

[339] 3-(5-(3-(3-(trifluoromethyl)piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0445]

[340] N-(2-nitrobenzyl)-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide,

[0446]

[341] (7-(3-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0447]

[342] (7-(3-nitro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0448]

[343] (7-(3-amino-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0449]

[344] (7-(6-(4-amino-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0450]

[345] (7-(3-(3-hydroxyazetidin-1-yl)-5-(isoxazol-4-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0451]

[346] 1-piperidyl-[7-[4-(1H-pyrazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone,

[0452]

[347] 1-piperidyl-[7-[4-(3-thienyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone,

[0453]

[348] [7-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0454]

[349] 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-3H-1,3,4-oxadiazol-2-one,

[0455]

[350] [7-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0456]

[351] [7-[4-(5-methylthiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0457]

[352] [7-[4-(1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0458]

[353] 3-(5-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0459]

[354] 3-(5-(3-(3-ethylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0460]

[355] (7-(6-(4-nitro-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0461]

[356] (7-(2-(4-amino-1H-pyrazol-1-yl)-6-bromopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0462]

[357] (7-(2-(3-hydroxyazetidin-1-yl)-6-(1-methyl-1H-pyrazol-5-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0463]

[358] 7-[4-(1,2-dimethylimidazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0464]

[359] [7-[4-(5-amino-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0465]

[360] 5-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one,

[0466]

[361] 1-piperidyl-[7-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone,

[0467]

[362] N-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide,

[0468]

[363] (7-(5-bromo-2-(3-(hydroxymethyl)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0469]

[364] [7-[6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0470]

[365] 1-piperidyl-[7-[6-(2-thioxo-3H-1,3,4-oxadiazol-5-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]methanone,

[0471]

[366] (7-(2-(isoxazol-4-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0472]

[367] 3-(6-(1-methyl-1H-pyrazol-5-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0473]

[368] 3-(6-(3,5-dimethylisoxazol-4-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0474]

[369] (7-(2-(1-methyl-1H-pyrazol-5-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0475]

[370] 3-(5'-fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[2,3'-bipyridin]-6-yl)oxazolidin-2-one,

[0476]

[371] (7-(2-(3,5-dimethylisoxazol-4-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0477]

[372] 3-(6-(2-methylpyrimidin-5-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0478]

[373] 5-[3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one,

[0479]

[374] (7-(5-(1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0480]

[375] (7-(6-(3-(dimethylamino)azetidin-1-yl)-5'-fluoro-[2,3'-bipyridin]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0481]

[376] (7-(5'-fluoro-6-morpholino-[2,3'-bipyridin]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0482]

[377] (7-(2-(2-methylpyrimidin-5-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0483]

[378] 6-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0484]

[379] [7-[5-fluoro-6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0485]

[380] [7-[5-fluoro-6-(1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0486]

[381] [7-[6-(3,5-dimethylisoxazol-4-yl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0487]

[382] 6-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0488]

[383] 3-(5-(3-(3-fluoropiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0489]

[384] 3-(5-(3-(3,3-difluoropiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0490]

[385] (R)-6-(3-(3-methylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindoline-1-one,

[0491]

[386] (S)-6-(3-(3-methylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindoline-1-one,

[0492]

[387] 6-(3-(3-methylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindoline-1-one,

[0493]

[388] N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetamide,

[0494]

[389] 2-phenyl-N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide,

[0495]

[390] 6-(3-(2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridine-7-yl)isoindoline-1-one,

[0496]

[391] 6-(3-(6-azaspiro[3.4]octane-6-carbonyl)pyrazolo[1,5-a]pyridine-7-yl)isoindoline-1-one,

[0497]

[392] 6-(3-(7-azaspiro[3.5]nonan-7-carbonyl)pyrazolo[1,5-a]pyridine-7-yl)isoindoline-1-one,

[0498]

[393] 6-(3-(3-ethylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindoline-1-one,

[0499]

[394] [7-[5-fluoro-6-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0500]

[395] (7-(1-((1,2,4-oxadiazol-3-yl)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0501]

[396] 3-((4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-1H-pyrazol-1-yl)methyl)-1,2,4-oxadiazol-5(4H)-one,

[0502]

[397] (7-(2-(1-((1,2,4-oxadiazol-3-yl)methyl)-1H-pyrazol-4-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0503]

[398] 6-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0504]

[399] [7-[2-(3,5-dimethylisoxazol-4-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0505]

[400] 6-(3-(3-isopropylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0506]

[401] 6-(3-(1,2,3,6-tetrahydropyridine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0507]

[402] 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide,

[0508]

[403] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyrimidin-5-yl)acetamide,

[0509]

[404] [7-[2-[5-(difluoromethyl)-1-oxo-1,3,4-thiadiazol-2-yl]pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0510]

[405] 6-(3-(6-azaspiro[3.5]nonane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0511]

[406] 2-(4-chlorophenoxy)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide,

[0512]

[407] N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-2-pyrimidin-5-yl-acetamide,

[0513]

[408] N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-2-[6-(trifluoromethyl)-3-pyridyl]acetamide,

[0514]

[409] 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide,

[0515]

[410] 2-(4-chlorophenoxy)-N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]acetamide,

[0516]

[411] 6-(3-(6-fluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0517]

[412] 6-(3-(6,6-difluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one and

[0518]

[413] 3-hydroxy-5-[2-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-6-yl]pyridin-2-carbonitrile.

[0519] The compound represented by the above Formula 1 according to the present invention can be produced and used in the form of prodrugs, hydrates, solvates and pharmaceutically acceptable salts to enhance absorption in vivo or increase solubility, therefore, prodrugs, hydrates, solvates and pharmaceutically acceptable salts are also included in the scope of the present invention.

[0520] The term "prodrug" refers to a substance that is converted in vivo into the parent drug. Prodrugs are often used because, in some cases, they are easier to administer than the original parent drug. For example, they may be orally bioavailable, while the parent drug may not be. Prodrugs may also have improved solubility in pharmaceutical compositions compared to the parent drug. For example, prodrugs can be in vivo hydrolyzable esters of the compounds of the present invention and their pharmaceutically acceptable salts. Another example of a prodrug can be a short peptide (polyamino acid) linked to an acidic group that is metabolized to reveal the active site of the peptide.

[0521] The term "hydrate" means a compound of the present invention or a salt thereof containing a stoichiometric or non-stoichiometric amount of water bound by non-covalent intermolecular forces.

[0522] The term "solvate" means a compound of the present invention or a salt thereof that contains a stoichiometric or non-stoichiometric amount of a solvent bound by non-covalent intermolecular forces. Preferred solvents for this purpose include those that are volatile, non-toxic, and / or suitable for human administration.

[0523] The term "isomer" means compounds of the present invention or their salts that have the same chemical formula or molecular formula but are structurally or sterically different. Such isomers include structural isomers, such as tautomers, and stereoisomers, such as R- or S-isomers having an asymmetric carbon center, and geometric isomers (trans, cis). All these isomers and mixtures thereof are also included within the scope of the present invention.

[0524] The term "pharmaceutically acceptable salt" means a salt form of a compound that does not cause serious irritation to the body into which the compound is administered and does not impair the biological activity and physical properties of the compound. Pharmaceutical salts include acid addition salts formed by acids that form non-toxic acid addition salts containing pharmaceutically acceptable anions, for example, inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid, phosphoric acid, hydrobromic acid, hydroiodic acid, etc., organic carboxylic acids such as tartaric acid, formic acid, citric acid, acetic acid, trichloroacetic acid, trifluoroacetic acid, gluconic acid, benzoic acid, lactic acid, fumaric acid, maleic acid, salicylic acid, etc., sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc. For example, pharmaceutically acceptable salts of carboxylic acids include metal salts or alkaline earth metal salts formed with lithium, sodium, potassium, calcium, magnesium, etc.; salts of amino acids such as lysine, arginine, guanidine, etc.; organic salts such as dicyclohexylamine, N-methyl-D-glucamine, tris(hydroxymethyl)methylamine, diethanolamine, choline and triethylamine. The compound of Formula 1 according to the present invention can be converted into a salt thereof by a conventional method.

[0525] The present invention also provides a method for producing a compound of Formula 1.

[0526] The methods for preparing the compounds of Formula 1 of the present invention are illustrated in Schemes 1-55, and the methods for preparing the compounds of Formula 1 of the present invention are not intended to limit the methods for preparing the compounds of Formula 1 of the present invention. The methods for preparing the compounds shown in Reaction Schemes 1-55 are merely examples, and it is obvious that those skilled in the art can easily modify them depending on the specific substituents.

[0527] The present invention also provides a pharmaceutical composition for the prevention or treatment of a disease associated with 15-PGDH, comprising, as an active ingredient, a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

[0528] The present invention also provides a method for preventing or treating a disease associated with 15-PGDH, comprising administering to a subject in need thereof a therapeutically effective amount of a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

[0529] The present invention also provides the use of a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, as an effective ingredient for the manufacture of a medicament for the prevention or treatment of a disease associated with 15-PGDH.

[0530] In one embodiment, the 15-PGDH-related disease may be one or more selected from the group consisting of inflammatory disease (inflammatory bowel disease (ulcerative colitis, Crohn's disease), chronic obstructive pulmonary disease (COPD), Behcet's disease, acute liver injury, acute kidney injury, acute lung injury, sepsis, exacerbation of asthma and lung disease, peptic ulcer disease (e.g., NSAID-induced ulcer), vasculitis syndrome, non-alcoholic fatty liver disease (NAFLD), atopic dermatitis, psoriasis, interstitial cystitis, prostatitis syndrome), fibrosis (pulmonary fibrosis (idiopathic pulmonary fibrosis), renal fibrosis (glomerulosclerosis), cardiac fibrosis (myocardial fibrosis), oral fibrosis, deltoid fibrosis muscle, liver fibrosis, myelofibrosis, scleroderma), autoimmune disease (systemic lupus erythematosus, rheumatoid arthritis, autoimmune hepatitis, severe combined immunodeficiency (SCID)),ophthalmological disease (dry eye syndrome, conjunctivitis, keratitis), thrombocytopenia (drug-induced thrombocytopenia, autoimmune thrombocytopenia, idiopathic thrombocytopenia, viral thrombocytopenia), myopathy (muscular dystrophy, muscle injury), anemia (aplastic anemia, anemia of chronic disease, Fanconi anemia, beta-thalassemia, or anemia of unknown cause), circulatory system disease (heart disease (angina, heart failure, myocardial infarction), kidney disease (chronic kidney disease, renal failure), stroke, pulmonary hypertension, peripheral circulatory disorder), nerve cell death (mental disorders, neurodegenerative diseases, nerve injury), cytopenia (immune cytopenia, neutropenia, lymphopenia), osteoporosis, fracture, leukemia (acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myeloid leukemia (CML)),lymphoma (Hodgkin's lymphoma, non-Hodgkin's lymphoma), radiation toxicity, 15-PGDH-expressing cancer, multiple myeloma, paroxysmal nocturnal hemoglobinuria (PNH), pure red cell aplasia, megakaryocytosis, Wiskott-Aldrich syndrome, sickle cell anemia, Hurler syndrome, adrenoleukodystrophy, metachromatic leukodystrophy, myelodysplasia, Duchenne muscular dystrophy, solid tumors, chronic granulomatous disease, systemic sclerosis, scars, wounds, otologic diseases (dizziness, tinnitus, balance disorders), hair loss, skin aging, periodontal disease, diabetes, stem cell and bone marrow transplantation or organ transplantation, cervical ripening, Alzheimer's disease, and Parkinson's,

[0531] As a result of measuring the 15-PGDH inhibitory activity of the heterocyclic compound of the present invention, it was confirmed that it exhibited excellent 15-PGDH inhibitory activity.

[0532] The present invention also provides a pharmaceutical composition comprising a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive.

[0533] The above additives may include pharmaceutically acceptable carriers or diluents, and can be formulated into oral compositions such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols; external preparations; suppositories; and sterile injection solutions, respectively, according to conventional methods.

[0534] Pharmaceutically acceptable carriers include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methyl hydroxybenzoate, propyl hydroxybenzoate, talc, magnesium stearate, mineral oil, etc. In addition, diluents or excipients such as fillers, bulking agents, binders, wetting agents, disintegrating agents, and surfactants are included. Oral solid preparations include tablets, pills, powders, granules, capsules, etc., and these solid preparations may contain at least one excipient such as starch, calcium carbonate, sucrose or lactose, gelatin, etc., and may contain a lubricant such as magnesium stearate, talc, etc. Oral liquid preparations include suspensions, oral solutions, emulsions, syrups, etc.and may contain diluents such as water or liquid paraffin, wetting agents, sweeteners, flavoring agents, preservatives, etc. Preparations for parenteral administration include sterilized aqueous solutions, non-aqueous vehicles, suspensions, emulsions, creams, lyophilized preparations, suppositories, and non-aqueous vehicles and suspending agents include propylene glycol, polyethylene glycol, vegetable oils such as olive oil, and injectable esters such as ethyl oleate. Suppository bases that can be used include witepsol, macrogol, Tween 61, cocoa butter, lauric fat, and glycerogelatin.

[0535] The dosage of the active ingredient contained in the pharmaceutical composition of the present invention varies depending on the patient's condition and body weight, the degree of the disease, the form of the active ingredient, the route and period of administration, and can be appropriately adjusted depending on the patient. For example, the active ingredient can be administered at a dose of 0.0001 to 1000 mg / kg per day, preferably 0.001 to 100 mg / kg, and such a dose can be administered once a day or divided into multiple administrations. In addition, the pharmaceutical composition of the present invention can contain the active ingredient in an amount of 0.001 to 90% by weight, based on the total weight of the composition.

[0536] The pharmaceutical composition of the present invention can be administered to mammals such as rats, mice, livestock and humans by various routes, such as orally, cutaneously, intraperitoneally, rectally, or by intravenous, intramuscular, subcutaneous, intrauterine or intracerebroventricular injection.

[0537] Next, the present invention will be described in more detail by means of Examples and Experimental Examples. However, the following Examples and Experimental Examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0538] Example 1. 7-phenylpyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0539] <Diagram 1>

[0540]

[0541] Step 1-1: Pyrazolo[1,5-a]pyridine-3-carboxylic acid (1.0 g, 6.18 mmol) was dissolved in tetrahydrofuran (20 mL), and the temperature was lowered to -20°C. Lithium bis(trimethylsilyl)amide dissolved in 1 M tetrahydrofuran (18.5 mL, 18.5 mmol) was slowly added thereto, and the mixture was stirred for 30 minutes. Iodine (1.878 g, 7.4 mmol) dissolved in tetrahydrofuran (5 mL) was added to the reaction solution, and the mixture was stirred for 30 minutes, then the temperature was slowly raised to room temperature, and the mixture was stirred for 12 hours. After completion of the reaction, saturated aqueous sodium bicarbonate solution (50 mL) was added, and dichloromethane (50 mL × 3) was used for extraction. The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. After quenching with a small amount of dichloromethane, filtration, and air drying, the target compound 1-1 (1.86 g, 94%) was obtained.

[0542] Step 1-2: Compound 1-1 (1.7 g, 5.9 mmol) was dissolved in N,N-dimethylformamide (30 mL), HATU (2.69 g, 7.1 mmol) and DIPEA (3.1 mL, 17.7 mmol) were added, and the mixture was stirred at room temperature for 10 minutes. Piperidine (0.7 mL, 7.1 mmol) was added to the reaction solution, and the mixture was stirred for 4 hours. After completion of the reaction, the reaction solution was concentrated, diluted with ethyl acetate (100 mL), and washed successively with water (50 mL), saturated aqueous ammonium chloride solution (50 mL), saturated aqueous sodium bicarbonate solution (50 mL), and saturated brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. After solidification using diethyl ether / ethyl acetate (10:1) solution (20 mL), filtration and air drying were performed to obtain the target compound 1-2 (1.51 g, 72%).[HATU (1-[Bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate, azabenzotriazoletetramethyluronium hexafluorophosphate), DIPEA (N,N-Diisopropylethylamine)].

[0543] Step 1-3: Compound 1-2 (70 mg, 0.19 mmol) was dissolved in 1,4-dioxane (7 mL), benzeneboronic acid (24 mg, 0.19 mmol), tetrakis(triphenylphosphine)palladium (57 mg, 0.04 mmol) and 2 M aqueous potassium carbonate solution (0.19 mL, 0.39 mmol) were added and nitrogen was passed through for 10 minutes, and then the mixture was stirred at 100 °C for 12 hours. After completion of the reaction, the reaction solution was concentrated and diluted with dichloromethane (10 mL). The remaining palladium was filtered off using diatomaceous earth (Celite), and the filtrate was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated and separated using column chromatography to give the title compound 1 (42.3 mg, 70%).

[0544] 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.23 ​​(s, 1H), 7.90 (dd, J=16.6, 8.4, 2.0 Hz, 3H), 7.60-7.45 (m, 4H), 7.16 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t,J=5.4 Hz, 4H), 1.65 (s, 2H), 1.60-1.43 (m, 4H).

[0545] MS (ESI, LR) Calculated for C 19 H 20 N3O [M+H] + : 306.2, found: 306.2

[0546] Example 2. (7-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0547] Example 3. Methyl 3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate

[0548] Example 4. (7-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0549] Example 5. (7-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0550] Example 6. 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0551] Example 8. (7-(2-chloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0552] Example 10. 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoic acid

[0553] Example 11. Methyl 4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate

[0554] Example 12. (7-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0555] Example 13. (7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0556] Example 15. 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0557] Example 16. (7-(6-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0558] Example 18. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinonitrile

[0559] Example 19. (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0560] Example 20. (7-(4-methoxy-3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0561] Example 21. (7-(3-chloro-4-hydroxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone]

[0562] Example 22. 2-fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0563] Example 23. 2-(dimethylamino)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0564] Example 24. (7-(3,4-dimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0565] Example 25. (7-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0566] Example 120. tert-butyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate

[0567] Example 121. (7-(benzo[d][1,3]dioxol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0568] Example 122. (7-(benzofuran-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0569] Example 123. (7-(benzofuran-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0570] Example 124. (7-(benzo[b]thiophen-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0571] Example 125. (7-(1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0572] Example 126. (7-(1H-indol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0573] Example 127. (7-(benzofuran-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0574] Example 128. (7-(naphthalen-1-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0575] Example 129. (7-(naphthalen-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0576] Example 130. piperidin-1-yl(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[0577] Example 131. 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[0578] Example 134. 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one

[0579] Example 136. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[0580] Example 138. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one

[0581] Example 140. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[0582] Example 143. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[0583] Example 145. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinolin-2(1H)-one

[0584] Example 195. 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

[0585] Example 205. 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carbonitrile

[0586] Example 207. 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-4(3H)-one

[0587] Example 224. 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1(2H)-one

[0588] Example 232. 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one

[0589] Example 233. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1(2H)-one

[0590] Example 244. Methyl 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylate

[0591] Example 245. 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one

[0592] Example 246. 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

[0593] Example 251. 3-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one

[0594] Example 252. 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one

[0595] Example 254. 2-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile

[0596] Example 255. 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[2,3-d]pyrimidin-4(3H)-one

[0597] Example 256. 3-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[3,2-d]pyrimidin-4(3H)-one

[0598] Example 264. (7-(2-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0599] Example 265. (7-(5-bromo-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0600] Example 266. (7-(2,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0601] Example 267. (7-(2-chloropyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0602] Example 268. 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzo[d]isoxazol-3(2H)-one

[0603] Example 269. (7-(3-methoxybenzo[d]isoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0604] Example 270. 2-(dimethylamino)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinonitrile

[0605] Example 271. (7-(6-fluoropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0606] Example 272. (7-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0607] Example 273. (7-(2,6-difluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0608] Example 279. (7-(3-chloro-5-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0609] Example 280. 5,6-dimethyl-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one

[0610] Example 281. (7-(6-chloro-5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0611] Example 282. (7-(2,6-dichloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0612] Example 283. (7-(5-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0613] Example 284. (7-(5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0614] Example 285. 3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile

[0615] Example 288. (7-(5,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0616] Example 289. (7-(5-chloro-6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0617] Example 290. 2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0618] Example 291. 3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0619] Example 292. (7-(4-bromophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0620] Example 293. 5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidine-2-carbonitrile

[0621] Example 294. [7-(2-hydroxypyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0622] Example 298. (7-(5-chloro-2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0623] Example 312. 3-nitro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0624] Example 313. (7-(6-bromopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0625] Example 314. (7-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0626] Example 315. (7-(6-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0627] Example 318. (7-(5-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0628] For Examples 2, 3, 4, 5, 6, 8, 10, 11, 12, 13, 15, 16, 18, 19, 20, 21, 22, 23, 24, 25, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 131, 134, 136, 138, 140, 143, 145, 195, 205, 207, 224, 232, 233, 244, 245, 246, 251, 252, 254, 255, 256, 264, 265, 266, 267, 268, 269, 270, 271, 272, 273, 279, 280, 281, 282, 283, 284, 285, 288, 289, 290, 291, 292, 293, 294, 298, 312, 313, 314, 315, 318 compounds were obtained by the same synthetic method as in Step 1-3 in Example 1, using the corresponding compounds and compound 1-2. The structural and spectral data are shown in Table 1 below.

[0629] Table 1 Example Structure 1H NMR MS 2 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (s, 1H), 8.05 (d, J=2.1 Hz, 1H), 7.93-7.84 (m, 2H), 7.64-7.56 (m, 2H), 7.52 (dd, J=8.9, 7.0 Hz, 1H), 7.24 (dd, J=7.1, 1.3 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=6.5 Hz, 2H), 1.57 (d, J=8.4 Hz, 4H). MS(ESI, LR) Calculated for C19H19ClN3O [M+H]+: 340.1, found: 340.1. 3 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.53 (t, J=1.8 Hz, 1H), 8.27 (s, 1H), 8.18 (dt, J=7.8, 1.5 Hz, 1H), 8.12 (dt, J=7.8, 1.4 Hz, 1H), 7.92 (dd, J=8.9, 1.4 Hz, 1H), 7.73 (t, J=7.8 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.25 (dd, J=7.0, 1.4 Hz, 1H), 3.90 (s, 3H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.57 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C21H22N3O3 [M+H]+: 364.2, found: 364.2. 4 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.23 ​​(s, 1H), 7.88 (dd, J=8.9, 1.4 Hz, 1H), 7.53-7.45 (m, 4H), 7.18 (dd, J=7.0, 1.4 Hz, 1H), 7.14-7.08 (m, 1H), 3.83 (s, 3H), 3.62 (t, J=5.4 Hz, 4H), 1.69-1.61 (m, 2H), 1.61-1.51 (m, 4H). MS(ESI, LR) Calculated for C20H22N3O2 [M+H]+: 336.2, found: 336.1. 5 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.87 (t, J=2.0 Hz, 1H), 8.42-8.35 (m, 2H), 8.29 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.87 (t, J=8.0 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.7 Hz, 2H), 1.57 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C19H19N4O3 [M+H]+: 351.1, found: 351.1. 6 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.21 (s, 1H), 7.83 (dd, J=8.9, 1.4 Hz, 1H), 7.47 (dd, J=8.9, 7.0 Hz, 1H), 7.17 (d, J=7.8 Hz, 1H), 7.09 (t, J=2.0 Hz, 1H), 7.05 (dd, J=7.1, 1.4 Hz, 1H), 6.99-6.94 (m, 1H), 6.75-6.68 (m, 1H), 5.27 (s, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.2 Hz, 2H), 1.57 (c, 4H). MS(ESI, LR) Calculated for C20H19N4O [M+H]+: 331.2, found: 331.2. 8 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.62 (d, J=5.2 Hz, 1H), 8.30 (s, 1H), 8.17 (d, J=1.5 Hz, 1H), 8.03-7.94 (m, 2H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.43 (dd, J=7.1, 1.3 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.62-1.52 (m, 4H). MS(ESI, LR) Calculated for C18H18ClN4O [M+H]+: 341.1, found: 341.0. 10 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (s, 1H), 8.08 (q, J=8.5 Hz, 4H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.25 (dd, J=7.0, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.72-1.61 (m, 2H), 1.58-1.54 (m, 4H). MS(ESI, LR) Calculated for C20H20N3O3 [M+H]+: 350.1, found: 350.2. 11 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (s, 1H), 8.18-8.06 (m, 4H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.0, 1.4 Hz, 1H), 3.92 (s, 3H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C21H22N3O3 [M+H]+: 364.2, found: 364.2. 12 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.24 (s, 1H), 8.02-7.93 (m, 2H), 7.89 (dd, J=8.9, 1.3 Hz, 1H), 7.68-7.58 (m, 27, 51, J=9.9), (dd, J=8.9). 7.1 Hz, 1H), 7.20 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=8.2 Hz, 2H), 1.57 (d, J=7.7 Hz, 4H). MS(ESI, LR) Calculated for C19H19ClN3O [M+H]+: 340.1, found: 340.0. 13 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.46-8.36 (m, 2H), 8.32-8.20 (m, 3H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 1.1 Hz, Hz), 7.33 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.2 Hz, 2H), 1.62-1.45 (m, 4H). MS(ESI, LR) Calculated for C19H19N4O3 [M+H]+: 351.1, found: 351.1. 15 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.26 (s, 1H), 8.20-8.11 (m, 2H), 8.09-7.99 (m, 2H), 7.94 (dd, J=8.9, 1.3 Hz, 1.3 Hz, 7.9, J=8.9, J 7.0 Hz, 1H), 7.28 (dd, J=7.0, 1.3 Hz, 1H), 3.62 (t, J=5.5 Hz, 4H), 1.71-1.62 (m, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C20H19N4O [M+H]+: 331.2, found: 331.2. 16 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.21 (d, J=2.2 Hz, 1H), 8.87 (dd, J=8.5, 2.3 Hz, 1H), 8.51 (d, J=8.4 Hz, 1H), 8.29 (s, 1H), 8.00 (dd, J=8.9, 1.3 Hz, 1H), 7.67-7.64 (m, 1H), 7.46 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.4 Hz, 2H), 1.57 (d, J=7.1 Hz, 4H). MS(ESI, LR) Calculated for C18H18N5O3 [M+H]+: 352.1, found: 352.1. 18 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.30 (d, J=2.2 Hz, 1H), 8.68 (dd, J=8.2, 2.2 Hz, 1H), 8.30-8.24 (m, 2H), 7.98 (dd, J=8.9, 1.3 Hz, 1H), 7.65 (t, J=1.3 Hz, 1H), 7.44-7.39 (m, 1H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=7.9 Hz, 2H), 1.56 (s, 4H). MS(ESI, LR) Calculated for C19H18N5O [M+H]+: 332.1, found: 332.1. 19 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.77 (d, J=2.5 Hz, 1H), 8.60 (td, J=8.3, 2.5 Hz, 1H), 8.25 (d, J=5.6 Hz, 1H), 7.93 (d, J=8.9 Hz, 1H), 7.65 (s, 1H), 7.41 (dd, J=8.6, 2.8 Hz, 1H), 7.30 (d, J=7.1 Hz, 1H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=6.0 Hz, 2H), 1.56 (s, 4H). MS(ESI, LR) Calculated for C18H18FN4O [M+H]+: 325.1, found: 325.1. 20 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.27 (d, J=2.7 Hz, 2H), 8.20 (dd, J=8.8, 2.3 Hz, 1H), 7.88 (dd, J=8.8, 1.3 Hz, 1H), 7.55-7.43 (m, 2H), 7.24 (dd, J=7.1, 1.4 Hz, 1H), 4.00 (s, 3H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.4 Hz, 2H), 1.61-1.49 (m, 4H). MS(ESI, LR) Calculated for C21H21F3N3O2 [M+H]+: 404.2, found: 404.1. 21 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (s, 1H), 8.04 (d, J=2.2 Hz, 1H), 7.83 (dd, J=8.9, 1.3 Hz, 1H), 7.74 (dd, J=8.5, 2.3 Hz, 1H), 7.48 (dd, J=8.9, 7.1 Hz, 1H), 7.15 (dd, J=7.1, 1.4 Hz, 1H), 7.12 (d, J=8.6 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.0 Hz, 2H), 1.57 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C19H19ClN3O2 [M+H]+: 356.1, found: 356.1. 22 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.28 (s, 1H), 8.20 (dd, J=10.8, 1.5 Hz, 1H), 8.13 (dd, J=8.2, 6.9 Hz, 1H), 8.02 (dd, J=8.2, 1.6 Hz, 1H), 7.96 (dd, J=8.9, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.36 (dd, J=7.1, 1.3 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=8.2 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C20H18FN4O [M+H]+: 349.1, found: 349.1. 23 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.24 (s, 1H), 7.92 (dd, J=9.0, 1.4 Hz, 1H), 7.76 (d, J=8.1 Hz, 1H), 7.55-7.49 (m, 2H), 7.43 (dd, J=8.1, 1.5 Hz, 1H), 7.27 (dd, J=7.1, 1.3 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 3.06 (s, 6H), 1.65 (d, J=7.4 Hz, 2H), 1.62-1.53 ​​(m, 4H). MS(ESI, LR) Calculated for C22H24N5O [M+H]+: 374.2, found: 374.2. 24 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.24 (s, 1H), 7.84 (dd, J=8.9, 1.3 Hz, 1H), 7.64-7.61 (m, 2H), 7.49 (dd, J=8.9, 7.0 Hz, 1H), 7.17 (dd, J=7.0, 1.4 Hz, 1H), 7.13 (d, J=8.3 Hz, 1H), 3.85 (s, 3H), 3.82 (s, 3H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=6.9 Hz, 2H), 1.57 (d, J=8.4 Hz, 4H). MS(ESI, LR) Calculated for C21H24N3O3 [M+H]+: 366.2, found: 366.1. 25 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (s, 1H), 7.97 (dd, J=9.0, 1.4 Hz, 1H), 7.61 (d, J=1.9 Hz, 1H), 7.52 (dd, J=8.9, 7.0 Hz, 1H), 7.22 (dd, J=7.0, 1.3 Hz, 1H), 6.69 (d, J=1.9 Hz, 1H), 3.74 (s, 3H), 3.62 (t, J=5.5 Hz, 4H), 1.70-1.61 (m, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C17H20N5O [M+H]+: 310.2, found: 310.1. 120 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.24 (d, J=5.2 Hz, 1H), 7.82 (dd, J=15.5, 8.7 Hz, 1H), 7.43 (dt, J=8.9, 6.3 Hz, 1H), 7.02 (dd, J=23.5, 7.1 Hz, 1H), 6.51 (d, J=27.0 Hz, 1H), 4.10 (s, 2H), 3.60 (t, J=5.3 Hz, 6H), 2.68 (s, 2H), 1.64 (s, 2H), 1.56 (s, 4H), 1.46 (d, J=4.8 Hz, 9H). MS(ESI, LR) Calculated for C23H31N4O3 [M+H]+: 411.2, found: 411.2. 121 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.23 ​​(s, 1H), 7.84 (dd, J=8.9, 1.3 Hz, 1H), 7.53 (d, J=1.7 Hz, 1H), 7.48 (dd, J=8.9, 7.1 Hz, 1H), 7.43 (dd, J=8.1, 1.8 Hz, 1H), 7.13 (dd, J=7.1, 1.4 Hz, 1H), 7.10 (d, J=8.1 Hz, 1H), 6.14 (s, 2H), 3.62 (t, J=5.3 Hz, 4H), 1.65 (s, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C20H20N3O3 [M+H]+: 350.1, found: 350.1. 122 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.16 (s, 1H), 8.36 (s, 1H), 8.03 (d, J=7.8 Hz, 1H), 7.93 (dd, J=8.8, 1.4 Hz, 1H), 7.79 (d, J=8.1 Hz, 1H), 7.68 (dd, J=7.2, 1.4 Hz, 1H), 7.60 (dd, J=8.8, 7.1 Hz, 1H), 7.53-7.46 (m, 1H), 7.46-7.40 (m, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.5 Hz, 2H), 1.58 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C21H20N3O2 [M+H]+: 346.2, found: 346.1. 123 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.47 (d, J=1.6 Hz, 2H), 7.97 (dd, J=8.8, 1.3 Hz, 1H), 7.91-7.82 (m, 2H), 7.74 (d, J=8.3 Hz, 1H), 7.63 (dd, J=8.8, 7.3 Hz, 1H), 7.48 (td, J=7.8, 1.3 Hz, 1H), 7.37 (t, J=7.5 Hz, 1H), 3.65 (t, J=5.4 Hz, 4H), 1.67 (d, J=6.2 Hz, 2H), 1.59 (s, 4H). MS(ESI, LR) Calculated for C21H20N3O2 [M+H]+: 346.2, found: 346.1. 124 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.33 (s, 1H), 8.19 (s, 1H), 8.13 (d, J=8.0 Hz, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.60-7.34 (m, 4H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.64 (dd, J=7.8, 3.6 Hz, 2H), 1.57 (td, J=6.6, 3.4 Hz, 4H). MS(ESI, LR) Calculated for C21H20N3OS [M+H]+: 362.1, found: 362.1. 125 1H NMR (400 MHz, DMSO-d6) δ(ppm): 13.32 (s, 1H), 8.25 (s, 1H), 8.18 (d, J=3.9 Hz, 2H), 7.97-7.83 (m, 2H), 7.62-7.49 (m, 2H), 7.26 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=7.2 Hz, 2H), 1.57 (d, J=6.9 Hz, 4H). MS(ESI, LR) Calculated for C20H20N5O [M+H]+: 346.2, found: 346.1. 126 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.34 (s, 1H), 8.23 ​​(s, 1H), 8.19-8.12 (m, 1H), 7.83 (dd, J=8.8, 1.3 Hz, 1H), 7.64 (dd, J=8.5, 1.7 Hz, 1H), 7.57-7.42 (m, 3H), 7.14 (dd, J=7.1, 1.4 Hz, 1H), 6.56 (t, J=2.6 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=7.6 Hz, 2H), 1.57 (d, J=6.9 Hz, 4H). MS(ESI, LR) Calculated for C21H21N4O [M+H]+: 345.2, found: 345.1. 127 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.24 (d, J=2.1 Hz, 2H), 8.12 (d, J=2.2 Hz, 1H), 7.86 (ddd, J=15.3, 8.8, 1.6 Hz, 2H), 7.77 (d, J=8.6 Hz, 1H), 7.52 (dd, J=8.9, 7.0 Hz, 1H), 7.19 (dd, J=7.0, 1.4 Hz, 1H), 7.09 (d, J=2.2 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.69-1.62 (m, 2H), 1.57 (q, J=5.8 Hz, 4H). MS(ESI, LR) Calculated for C21H20N3O2 [M+H]+: 346.2, found: 346.1. 128 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.17-8.11 (m, 1H), 8.06 (d, J=6.4 Hz, 2H), 8.00 (dd, J=9.0, 1.4 Hz, 1H), 7.71-7.66 (m, 2H), 7.62-7.53 (m, 2H), 7.42 (ddd, J=8.3, 6.8, 1.3 Hz, 1H), 7.22-7.14 (m, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.3 Hz, 2H), 1.57 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C23H22N3O [M+H]+: 356.2, found: 356.1. 129 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.51 (d, J=1.6 Hz, 1H), 8.27 (s, 1H), 8.12-7.99 (m, 4H), 7.93 (dd, J=8.8, 1.4 Hz, 1H), 7.69-7.49 (m, 3H), 7.31 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.6 Hz, 2H), 1.58 (d, J=7.1 Hz, 4H). MS(ESI, LR) Calculated for C23H22N3O [M+H]+: 356.2, found: 356.1. 130 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.39 (d, J=2.2 Hz, 1H), 8.98 (d, J=2.2 Hz, 1H), 8.30 (s, 1H), 8.13 (d, J=8.3 Hz, 2H), 7.97 (dd, J=8.9, 1.3 Hz, 1H), 7.94-7.84 (m, 1H), 7.78-7.67 (m, 1H), 7.60 (dd, J=8.9, 7.0 Hz, 1H), 7.43 (dd, J=7.0, 1.3 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=6.2 Hz, 2H), 1.58 (d, J=7.7 Hz, 4H). MS(ESI, LR) Calculated for C22H21N4O [M+H]+: 357.2, found: 357.1. 131 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.40 (d, J=2.0 Hz, 1H), 8.24 (s, 1H), 8.07 (s, 1H), 8.00 (dd, J=7.9, 2.0 Hz, 1H), 7.89 (dd, J=8.9, 1.4 Hz, 1H), 7.51 (dd, J=9.3, 7.3 Hz, 2H), 7.19 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.45 (td, J=6.5, 2.7 Hz, 2H), 3.01 (t, J=6.5 Hz, 2H), 1.68-1.62 (m, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H23N4O2 [M+H]+: 375.2, found: 375.1. 134 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.42 (d, J=5.6 Hz, 1H), 8.78 (d, J=2.0 Hz, 1H), 8.32-8.18 (m, 2H), 7.95-7.77 (m, 2H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.35-7.24 (m, 2H), 6.66 (d, J=7.1 Hz, 1H), 3.64 (t, J=5.5 Hz, 4H), 1.66 (s, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H21N4O2 [M+H]+: 373.2, found: 373.1. 136 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (s, 1H), 8.06 (s, 1H), 7.99 (d, J=8.6 Hz, 1H), 7.95-7.84 (m, 3H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.22 (dd, J=7.1, 1.3 Hz, 1H), 3.62 (t, J=5.6 Hz, 4H), 3.49-3.41 (m, 2H), 3.00 (t, J=6.6 Hz, 2H), 1.65 (d, J=5.4 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H23N4O2 [M+H]+: 375.2, found: 375.2. 138 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.38 (s, 1H), 8.31 (d, J=8.4 Hz, 1H), 8.27 (s, 1H), 8.22 (d, J=1.8 Hz, 1H), 7.99 (dd, J=8.3, 1.7 Hz, 1H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.8, 7.0 Hz, 1H), 7.34-7.19 (m, 2H), 6.65 (d, J=7.1 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (s, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H21N4O2 [M+H]+: 373.2, found: 373.2. 140 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.25 (d, J=3.2 Hz, 2H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.76 (d, J=7.8 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.1, 1.4 Hz, 1H), 4.50 (s, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.73-1.50 (m, 6H). MS(ESI, LR) Calculated for C21H21N4O2 [M+H]+: 361.2, found: 361.1. 143 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.72 (s, 1H), 8.25 (s, 1H), 8.14 (s, 1H), 8.00 (d, J=8.0 Hz, 1H), 7.94-7.89 (m, 1H), 7.83 (d, J=7.9 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.23 (d, J=7.0 Hz, 1H), 4.48 (s, 2H), 3.63 (t, J=5.5 Hz, 4H), 1.65 (s, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C21H21N4O2 [M+H]+: 361.2, found: 361.2. 145 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.97 (s, 1H), 8.33-8.20 (m, 2H), 8.06 (dd, J=8.6, 2.0 Hz, 1H), 8.01 (d, J=9.6 Hz, 1H), 7.88 (dd, J=8.9, 1.3 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.45 (d, J=8.6 Hz, 1H), 7.21 (dd, J=7.0, 1.4 Hz, 1H), 6.58 (d, J=9.5 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=6.0 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H21N4O2 [M+H]+: 373.2, found: 373.1. 195 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.10 (d, J=2.3 Hz, 1H), 8.77 (d, J=2.3 Hz, 1H), 8.27 (s, 2H), 7.93 (dd, J=8.9, 1.4 Hz, 1H), 7.54 (dd, J=8.9, 7.1 Hz, 1H), 7.34 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.55 (td, J=6.7, 2.8 Hz, 2H), 3.16 (t, J=6.7 Hz, 2H), 1.65 (d, J=5.3 Hz, 2H), 1.57 (d, J=7.1 Hz, 4H). MS(ESI, LR) Calculated for C21H22N5O2 [M+H]+: 376.1, found: 376.1. 205 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.23 (t, J=1.6 Hz, 1H), 8.80 (dd, J=10.3, 1.7 Hz, 1H), 8.31 (s, 1H), 8.01 (dd, J=8.8, 1.4 Hz, 1H), 7.58 (dd, J=8.9, 7.1 Hz, 1H), 7.49 (dd, J=7.2, 1.4 Hz, 1H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=6.8 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C19H17FN5O [M+H]+: 350.1, found: 350.1. 207 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.64 (s, 1H), 8.40 (s, 1H), 8.25 (s, 1H), 8.04 (d, J=8.0 Hz, 2H), 7.59 (t, J=8.0 Hz, 1H), 3.62 (dt, J=10.9, 5.2 Hz, 4H), 3.49 (s, 3H), 1.65 (d, J=5.9 Hz, 2H), 1.56 (p, J=5.6 Hz, 4H). MS(ESI, LR) Calculated for C18H20N5O2 [M+H]+: 338.2, found: 338.1. 224 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.80 (s, 1H), 8.83 (d, J=1.8 Hz, 1H), 8.46 (dd, J=8.2, 1.4 Hz, 2H), 8.29 (s, 1H), 8.11 (d, J=8.3 Hz, 1H), 7.96 (dd, J=8.9, 1.4 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.3 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=6.2 Hz, 2H), 1.58 (s, 4H). MS(ESI, LR) Calculated for C21H20N5O2 [M+H]+: 374.2, found: 374.1. 232 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.24 (d, J=2.1 Hz, 1H), 8.94 (s, 1H), 8.67 (d, J=2.1 Hz, 1H), 8.27 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.38 (dd, J=7.1, 1.4 Hz, 1H), 4.56 (s, 2H), 3.62 (dt, J=10.9, 5.4 Hz, 6H), 1.71-1.53 ​​(m, 8H). MS(ESI, LR) Calculated for C20H20N5O2 [M+H]+: 362.2, found: 362.1. 233 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.78 (s, 1H), 8.52 (t, J=1.2 Hz, 1H), 8.46 (s, 1H), 8.37 (d, J=1.3 Hz, 2H), 8.29 (s, 1H), 7.97 (dd, J=8.9, 1.4 Hz, 1H), 7.58 (dd, J=8.9, 7.0 Hz, 1H), 7.35 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.7 Hz, 2H), 1.58 (d, J=6.3 Hz, 4H). MS(ESI, LR) Calculated for C21H20N5O2 [M+H]+: 374.2, found: 374.1. 244 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.12 (t, J=1.5 Hz, 1H), 8.63 (dd, J=11.6, 1.7 Hz, 1H), 8.31 (s, 1H), 7.99 (dd, J=8.9, 1.4 Hz, 1H), 7.58 (dd, J=8.9, 7.1 Hz, 1H), 7.48 (dd, J=7.1, 1.4 Hz, 1H), 3.96 (s, 3H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.2 Hz, 2H), 1.57 (d, J=7.3 Hz, 4H). MS(ESI, LR) Calculated for C20H20FN4O3 [M+H]+: 383.1, found: 383.1. 245 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.76 (d, J=2.1 Hz, 1H), 8.48 (s, 1H), 8.36 (dd, J=8.6, 2.2 Hz, 1H), 8.28 (s, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.83 (d, J=8.5 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.32 (dd, J=7.0, 1.3 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 3.55 (s, 3H), 1.66 (d, J=5.5 Hz, 2H), 1.57 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C22H22N5O2 [M+H]+: 388.2, found: 388.1. 246 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.82 (t, J=1.4 Hz, 1H), 8.33 (s, 1H), 7.92 (dd, J=8.8, 1.4 Hz, 1H), 7.77 (dd, J=9.8, 1.8 Hz, 1H), 7.53 (dd, J=8.8, 7.1 Hz, 1H), 7.44-7.35 (m, 2H), 3.61 (d, J=13.8 Hz, 7H), 1.66 (q, J=5.9 Hz, 2H), 1.58 (q, J=5.6 Hz, 4H). MS(ESI, LR) Calculated for C20H21N6O2 [M+H]+: 377.2, found: 377.1. 251 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.46 (s, 1H), 8.32-8.24 (m, 3H), 8.07 (dd, J=8.3, 1.8 Hz, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.34 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.55 (s, 3H), 1.66 (d, J=5.4 Hz, 2H), 1.57 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C22H22N5O2 [M+H]+: 388.2, found: 388.1. 252 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.30 (s, 1H), 8.00-7.92 (m, 3H), 7.54 (dd, J=8.9, 7.1 Hz, 1H), 7.39 (dd, J=7.1, 1.4 Hz, 1H), 7.15-7.10 (m, 1H), 3.62 (d, J=8.7 Hz, 7H), 1.69-1.63 (m, 2H), 1.57 (d, J=5.8 Hz, 4H). MS(ESI, LR) Calculated for C20H21N6O2 [M+H]+: 377.2, found: 377.1. 254 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.54 (dd, J=6.3, 2.4 Hz, 1H), 8.38 (ddd, J=8.9, 5.3, 2.4 Hz, 1H), 8.27 (s, 1H), 7.93 (dd, J=8.9, 1.4 Hz, 1H), 7.74 (t, J=9.1 Hz, 1H), 7.54 (dd, J=8.9, 7.1 Hz, 1H), 7.29 (dd, J=7.1, 1.3 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.2 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C20H18FN4O [M+H]+: 349.1, found: 349.1. 255 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.46 (d, J=2.5 Hz, 1H), 9.21 (d, J=2.5 Hz, 1H), 8.69 (s, 1H), 8.31 (s, 1H), 7.96 (dd, J=8.9, 1.4 Hz, 1H), 7.60-7.55 (m, 1H), 7.47 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.5 Hz, 4H), 3.56 (s, 3H), 1.66 (d, J=5.9 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C21H21N6O2 [M+H]+: 389.2, found: 389.2. 256 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.31 (d, J=2.1 Hz, 1H), 8.73 (d, J=2.1 Hz, 1H), 8.55 (s, 1H), 8.31 (s, 1H), 8.00 (dd, J=8.8, 1.4 Hz, 1H), 7.59 (dd, J=8.9, 7.0 Hz, 1H), 7.49 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.5 Hz, 4H), 3.59 (s, 3H), 1.66 (d, J=5.7 Hz, 2H), 1.58 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C21H21N6O2 [M+H]+: 389.2, found: 389.1. 264 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.16 (s, 1H), 7.95 (dd, J=9.0, 1.4 Hz, 1H), 7.66 (dd, J=8.4, 1.5 Hz, 1H), 7.63-7.56 (m, 2H), 7.53 (ddd, J=9.1, 6.6, 2.5 Hz, 2H), 7.08 (dd, J=6.9, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.74-1.60 (m, 2H), 1.57 (q, J=5.8 Hz, 4H). MS(ESI, LR) Calculated for C19H19ClN3O [M+H]+: 340.1, found: 340.1. 265 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.63 (d, J=7.3 Hz, 2H), 8.24 (s, 1H), 7.99 (dd, J=9.0, 1.3 Hz, 1H), 7.55 (dd, J=9.0, 7.0 Hz, 1H), 7.34-7.29 (m, 1H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=6.0 Hz, 2H), 1.57 (d, J=6.6 Hz, 4H). MS(ESI, LR) Calculated for C18H17BrFN4O [M+H]+: 403, found: 403. 266 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.54 (dt, J=9.3, 7.9 Hz, 1H), 8.23 ​​(s, 1H), 7.98 (dd, J=9.0, 1.4 Hz, 1H), 7.55 (dd, J=9.0, 7.0 Hz, 1H), 7.43 (dd, J=8.1, 2.4 Hz, 1H), 7.27 (dd, J=7.1, 1.3 Hz, 1H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (q, J=4.8 Hz, 2H), 1.56 (h, J=4.4 Hz, 4H). MS(ESI, LR) Calculated for C18H17F2N4O [M+H]+: 343.1, found: 343.1. 267 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.39 (s, 2H), 8.31 (s, 1H), 7.98 (dd, J=8.9, 1.4 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.45 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=8.2 Hz, 2H), 1.57 (d, J=5.7 Hz, 4H). MS(ESI, LR) Calculated for C17H17ClN5O [M+H]+: 342.1, found: 342.1. 268 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.39 (d, J=1.9 Hz, 1H), 8.30-8.24 (m, 2H), 7.91 (dd, J=8.9, 1.3 Hz, 1H), 7.69 (d, J=8.8 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.28 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (d, J=9.0 Hz, 7H), 1.66 (d, J=5.6 Hz, 2H), 1.57 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C21H21N4O3 [M+H]+: 377.2, found: 377.1. 269 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.35 (d, J=1.8 Hz, 1H), 8.26 (s, 1H), 8.20 (dd, J=8.8, 1.8 Hz, 1H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.82 (d, J=8.8 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 4.17 (s, 3H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.7 Hz, 2H), 1.57 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C21H21N4O3 [M+H]+: 377.2, found: 377.1. 270 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.91 (d, J=2.4 Hz, 1H), 8.67 (d, J=2.5 Hz, 1H), 8.27 (s, 1H), 7.85 (dd, J=8.9, 1.3 Hz, 1H), 7.50 (dd, J=8.9, 7.1 Hz, 1H), 7.29 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 3.34 (s, 6H), 1.65 (d, J=5.5 Hz, 2H), 1.57 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C21H23N6O [M+H]+: 375.2, found: 375.1. 271 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.77 (dd, J=7.6, 2.7 Hz, 1H), 8.35 (s, 1H), 8.25 (q, J=8.1 Hz, 1H), 8.00 (dd, J=8.8, 1.5 Hz, 1H), 7.72 (dd, J=7.2, 1.5 Hz, 1H), 7.59 (dd, J=8.8, 7.1 Hz, 1H), 7.37 (dd, J=8.2, 2.7 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.71-1.63 (m, 2H), 1.63-1.54 (m, 4H). MS(ESI, LR) Calculated for C18H18FN4O [M+H]+: 325.1, found: 325.1. 272 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.47 (d, J=7.8 Hz, 1H), 8.21 (d, J=7.7 Hz, 2H), 8.02 (dd, J=9.0, 1.4 Hz, 1H), 7.59 (dd, J=9.0, 7.0 Hz, 1H), 7.28 (dd, J=7.0, 1.3 Hz, 1H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=7.0 Hz, 2H), 1.57 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C19H17ClF3N4O [M+H]+: 409.1, found: 409.1. 273 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.33 (s, 1H), 8.02 (dd, J=8.8, 1.4 Hz, 1H), 7.88 (s, 2H), 7.57 (dd, J=8.8, 7.1 Hz, 1H), 7.51 (dd, J=7.1, 1.5 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.0 Hz, 2H), 1.57 (d, J=7.8 Hz, 4H). MS(ESI, LR) Calculated for C18H17F2N4O [M+H]+: 343.1, found: 343.1. 279 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.28 (s, 1H), 7.96-7.90 (m, 2H), 7.88-7.82 (m, 1H), 7.64 (dt, J=8.7, 2.2 Hz, 1H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.31 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.69-1.61 (m, 2H), 1.57 (q, J=5.9 Hz, 4H). MS(ESI, LR) Calculated for C19H18ClFN3O [M+H]+: 358.1, found: 358.1. 280 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.19 (d, J=2.0 Hz, 1H), 8.69 (d, J=1.9 Hz, 1H), 8.29 (s, 1H), 7.97 (dd, J=8.8, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.39-7.34 (m, 1H), 4.74 (sq., J=6.8 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.11 (s, 3H), 1.66 (d, J=5.5 Hz, 2H), 1.57 (s, 4H), 1.52 (d, J=6.7 Hz, 2H). MS(ESI, LR) Calculated for C22H24N5O2 [M+H]+: 390.2, found: 390.1. 281 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.88 (d, J=1.9 Hz, 1H), 8.64 (dd, J=9.8, 2.0 Hz, 1H), 8.30 (s, 1H), 7.97 (dd, J=8.9, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.41 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=4.5 Hz, 2H), 1.57 (d, J=6.1 Hz, 4H). MS(ESI, LR) Calculated for C18H17ClFN4O [M+H]+: 359.1, found: 359.1. 282 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.33 (s, 1H), 8.23 ​​(s, 2H), 8.00 (dd, J=8.7, 1.6 Hz, 1H), 7.58-7.49 (m, 2H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=7.6 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C18H17Cl2N4O [M+H]+: 375.1, found: 375. 283 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.57-8.52 (m, 2H), 8.24 (s, 1H), 7.99 (dd, J=9.0, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.32 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.2 Hz, 2H), 1.57 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C18H17ClFN4O [M+H]+: 359.1, found: 359.1. 284 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.99 (t, J=1.8 Hz, 1H), 8.76 (d, J=2.8 Hz, 1H), 8.40 (ddd, J=10.1, 2.8, 1.7 Hz, 1H), 8.28 (s, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (q, J=5.8 Hz, 2H), 1.57 (h, J=5.9 Hz, 4H). MS(ESI, LR) Calculated for C18H18FN4O [M+H]+: 325.1, found: 325.1. 285 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.21 (s, 1H), 8.14-8.06 (m, 1H), 7.99 (dd, J=8.9, 1.3 Hz, 1H), 7.94 (d, J=5.8 Hz, 2H), 7.55 (dd, J=9.0, 7.0 Hz, 1H), 7.24 (dd, J=7.0, 1.3 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.4 Hz, 2H), 1.61-1.46 (m, 4H). MS(ESI, LR) Calculated for C20H18FN4O [M+H]+: 349.1, found: 349.1. 288 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.72 (dd, J=11.1, 9.3, 2.0 Hz, 1H), 8.63 (t, J=1.8 Hz, 1H), 8.28 (s, 1H), 7.96 (dd, J=8.9, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.5 Hz, 4H), 1.72-1.62 (m, 2H), 1.57 (d, J=4.4 Hz, 4H). MS(ESI, LR) Calculated for C18H17F2N4O [M+H]+: 343.1, found: 343.1. 289 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.86 (dd, J=8.9, 2.2 Hz, 1H), 8.76-8.72 (m, 1H), 8.29 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.69-1.63 (m, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C18H17ClFN4O [M+H]+: 359.1, found: 359.1. 290 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.31 (s, 1H), 8.14 (d, J=9.9 Hz, 2H), 7.99 (dd, J=8.9, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.1 Hz, 1H), 7.42 (d, J=7.1 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.4 Hz, 2H), 1.58 (d, J=7.9 Hz, 4H). MS(ESI, LR) Calculated for C20H17F2N4O [M+H]+: 367.1, found: 367.1. 291 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.33 (t, J=1.5 Hz, 1H), 8.30-8.23 (m, 2H), 8.08-8.03 (m, 1H), 7.96 (dd, J=8.9, 1.4 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.5 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C20H18FN4O [M+H]+: 349.1, found: 349.1. 292 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.24 (s, 1H), 7.93-7.86 (m, 3H), 7.80-7.73 (m, 2H), 7.51 (dd, J=8.9, 7.1 Hz, 1H), 7.20 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.69-1.61 (m, 2H), 1.57 (td, J=6.8, 3.4 Hz, 4H). MS(ESI, LR) Calculated for C19H19BrN3O [M+H]+: 384.1, found: 384. 293 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.65 (s, 2H), 8.32 (s, 1H), 8.02 (dd, J=8.8, 1.5 Hz, 1H), 7.60 (dd, J=8.8, 7.0 Hz, 1H), 7.54 (dd, J=7.1, 1.5 Hz, 1H), 3.63 (dd, J=7.0, 4.1 Hz, 4H), 1.68-1.62 (m, 2H), 1.61-1.55 (m, 4H). MS(ESI, LR) Calculated for C18H17N6O [M+H]+: 333.1, found: 333.1. 294 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.66 (s, 2H), 8.20 (s, 1H), 7.64 (dd, J=8.8, 1.3 Hz, 1H), 7.39 (dd, J=8.8, 7.2 Hz, 1H), 6.99 (dd, J=7.2, 1.4 Hz, 1H), 3.61 (t, J=5.4 Hz, 4H), 1.72-1.61 (m, 2H), 1.56 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C17H18N5O2 [M+H]+: 324.1, found: 324.1 298 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.58 (s, 1H), 8.22 (s, 1H), 8.02 (dd, J=8.9, 1.3 Hz, 1H), 7.70 (d, J=2.6 Hz, 1H), 7.57 (dd, J=9.0, 6.9 Hz, 1H), 7.26-7.22 (m, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=7.8 Hz, 2H), 1.61-1.55 (m, 4H). MS(ESI, LR) Calculated for C18H17ClFN4O [M+H]+: 359.1, found: 359.1 312 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.18 (t, J=1.9 Hz, 1H), 8.90 (dt, J=7.0, 1.6 Hz, 2H), 8.33 (s, 1H), 7.99 (dd, J=8.8, 1.4 Hz, 1H), 7.58 (dd, J=8.9, 7.1 Hz, 1H), 7.48 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.7 Hz, 2H), 1.58 (s, 4H). MS(ESI, LR) Calculated for C20H18N5O3 [M+H]+: 376.1, found: 376.1 313 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.92 (d, J=2.5 Hz, 1H), 8.37 (dd, J=8.3, 2.6 Hz, 1H), 8.26 (s, 1H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.87 (d, J=8.4 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.32 (dd, J=7.1, 1.3 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.69-1.61 (m, 2H), 1.61-1.53 ​​(m, 4H). MS(ESI, LR) Calculated for C18H18BrN4O [M+H]+: 385.1, found: 385 314 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.95 (d, J=2.5 Hz, 1H), 8.48 (dd, J=8.4, 2.5 Hz, 1H), 8.26 (s, 1H), 7.94 (dd, J=8.9, 1.4 Hz, 1H), 7.74 (d, J=8.4 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.33 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.5 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C18H18ClN4O [M+H]+: 341.1, found: 341.1 315 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.41 (dd, J=9.2, 7.8 Hz, 1H), 8.23 ​​(s, 1H), 7.98 (dd, J=8.9, 1.4 Hz, 1H), 7.76 (dd, J=7.9, 1.1 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.28 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (q, J=5.0 Hz, 2H), 1.57 (q, J=6.0 Hz, 4H). MS(ESI, LR) Calculated for C18H17ClFN4O [M+H]+: 359.1, found: 359.0 318 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.50 (dd, J=6.2, 2.2 Hz, 2H), 9.27 (t, J=2.3 Hz, 1H), 8.32 (s, 1H), 8.00 (dd, J=8.9, 1.4 Hz, 1H), 7.58 (dd, J=8.9, 7.1 Hz, 1H), 7.50 (dd, J=7.0, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.82-1.62 (m, 2H), 1.57 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C18H18N5O3 [M+H]+: 352.1, found: 352.1

[0630] Example 7. (7-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0631] <Scheme 2>

[0632]

[0633] Compound 5 (0.331 g, 0.94 mmol) was dissolved in methanol (16.5 mL), and palladium / carbon (0.025 g, 0.24 mmol) was added. The reaction solution was filled with hydrogen gas and stirred for 12 hours. After completion of the reaction, the remaining palladium was removed using diatomaceous earth (Celite), and the filtrate was concentrated. Dichloromethane (30 mL) was added, and the mixture was washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated using column chromatography to give the target compound 7 (0.297 g, 95%).

[0634] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.21 (s, 1H), 7.83 (dd,J=8.9, 1.4 Hz, 1H), 7.47 (dd,J=8.9, 7.0 Hz, 1H), 7.17 (d,J=7.8 Hz, 1H), 7.09 (t,J=2.0 Hz, 1H), 7.05 (dd,J=7.1, 1.4 Hz, 1H), 6.99-6.94 (m, 1H), 6.75-6.68 (m, 1H), 5.27 (s, 2H), 3.62 (t,J=5.4 Hz, 4H), 1.65 (d,J=5.2 Hz, 2H), 1.57 (s, 4H).

[0635] MS(ESI, LR) Calculated for C 19 H21 N4O [M+H] + : 321.2, found: 321.2.

[0636] Example 9. (7-(5-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0637] Example 14. (7-(4-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0638] Example 17. (7-(6-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0639] For Examples 9, 14, and 17, compounds were obtained sequentially using the synthesis method of Step 1-3 of Example 1 and the synthesis method of Example 7, using the corresponding compounds and compound 1-2. The structural and spectral data are shown in Table 2 below.

[0640] Table 2 Example Structure 1H NMR MS 9 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.23 ​​(s, 1H), 8.16 (d, J=1.9 Hz, 1H), 8.06 (d, J=2.7 Hz, 1H), 7.87 (dd, J=8.9, 1.3 Hz, 1H), 7.53-7.46 (m, 2H), 7.15 (dd, J=7.0, 1.4 Hz, 1H), 5.54 (s, 2H), 3.61 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.2 Hz, 2H), 1.56 (d, J=7.7 Hz, 4H). MS(ESI, LR) Calculated for C18H20N5O [M+H]+: 322.2, found: 322.1. 14 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.21 (s, 1H), 7.75-7.68 (m, 3H), 7.43 (dd, J=8.8, 7.1 Hz, 1H), 7.03 (dd, J=7.2, 1.4 Hz, 1H), 6.68 (d, J=8.6 Hz, 2H), 5.59 (s, 2H), 3.61 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.56 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C19H21N4O [M+H]+: 321.2, found: 321.2. 17 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.51 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.02 (dd, J=8.7, 2.5 Hz, 1H), 7.78 (dd, J=8.8, 1.3 Hz, 1H), 7.46 (dd, J=8.8, 7.1 Hz, 1H), 7.11 (dd, J=7.1, 1.4 Hz, 1H), 6.57 (d, J=8.7 Hz, 1H), 6.43 (s, 2H), 3.61 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.56 (d, J=6.5 Hz, 4H). MS(ESI, LR) Calculated for C18H20N5O [M+H]+: 322.2, found: 322.1.

[0641] Example 26. (7-(3-(morpholine-4-carbonyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0642] <Diagram 3>

[0643]

[0644] Step 26-1: Using compound 1-2 and 3-boronobenzoic acid, the target compound 26-1 was obtained in the same synthetic method as in Step 1-3 in Example 1.

[0645] Step 26-2: Using compound 26-1 and morpholine, the target compound 26 was obtained in the same synthetic method as in Step 1-2 in Example 1.

[0646] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.03-7.92 (m, 3H), 7.65-7.54 (m, 2H), 7.38 (dd,J=8.9, 7.0 Hz, 1H), 6.98 (dd,J=7.0, 1.4 Hz, 1H), 3.78-3.60 (m, 12H), 1.74-1.66 (m, 6H).

[0647] MS(ESI, LR) Calculated for C 24 H 27 N4O3[M+H] + : 419.2, found: 419.2.

[0648] Example 27.N-methyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0649] Example 28.N-isopropyl-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0650] Example 29. azetidin-1-yl(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0651] Example 30.N-(2-methoxyethyl)-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0652] Example 31.N-(2-(dimethylamino)ethyl)-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0653] Example 32.N-(cyclopropylmethyl)-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0654] Example 33.N-(1-methylpiperidin-4-yl)-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0655] Example 35.tert-butyl 4-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridine-7-yl)benzoyl)piperazine-1-carboxylate

[0656] Example 36.N-(2-cyanoethyl)-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0657] Example 37. 3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide

[0658] Example 38. 3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide

[0659] For Examples 27, 28, 29, 30, 31, 32, 33, 35, 36, 37, and 38, compounds were obtained in the same synthetic method as in Step 1-2 in Example 1, using the corresponding compounds and compound 26-1. The structural and spectral data are shown in Table 3 below.

[0660] Table 3 Example Structure 1H NMR MS 27 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (t, J=1.8 Hz, 1H), 8.06 (s, 1H), 7.98 (ddd, J=8.9, 6.9, 1.4 Hz, 2H), 7.89 (dt, J=7.7, 1.5 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.38 (dd, J=8.9, 7.0 Hz, 1H), 6.98 (dd, J=7.0, 1.4 Hz, 1H), 6.33 (s, 1H), 3.04 (d, J=4.9 Hz, 3H), 1.70 (d, J=27.1 Hz, 10H). MS(ESI, LR) Calculated for C21H23N4O2 [M+H]+: 363.2, found: 363.2. 28 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.21 (t, J=1.8 Hz, 1H), 8.06 (s, 1H), 8.02-7.93 (m, 2H), 7.87 (dt, J=7.8, 1.5 Hz, 1H), 7.60 (t, J=7.8 Hz, 1H), 7.39 (dd, J=8.9, 7.0 Hz, 1H), 6.98 (dd, J=6.9, 1.4 Hz, 1H), 6.01 (d, J=7.7 Hz, 1H), 4.31 (dq, J=13.4, 6.7 Hz, 1H), 3.72 (t, J=5.4 Hz, 4H), 1.73-1.72 (m, 2H), 1.59 (s, 4H), 1.28 (d, J=6.6 Hz, 6H). MS(ESI, LR) Calculated for C23H27N4O2 [M+H]+: 391.2, found: 391.2. 29 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.16 (t, J=1.8 Hz, 1H), 8.06 (s, 1H), 8.02-7.93 (m, 2H), 7.77 (dt, J=7.7, 1.5 Hz, 1H), 7.58 (t, J=7.8 Hz, 1H), 7.38 (dd, J=8.9, 7.0 Hz, 1H), 6.98 (dd, J=7.0, 1.4 Hz, 1H), 4.40 (t, J=7.8 Hz, 2H), 4.26 (t, J=7.9 Hz, 2H), 3.72 (t, J=5.4 Hz, 4H), 2.43-2.32 (m, 2H), 1.78-1.70 (m, 2H), 1.70-1.64 (m, 4H). MS(ESI, LR) Calculated for C23H25N4O2 [M+H]+: 389.2, found: 389.2. 30 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.06 (s, 1H), 8.03-7.96 (m, 2H), 7.91 (dt, J=7.9, 1.5 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.39 (dd, J=8.9, 7.0 Hz, 1H), 6.98 (dd, J=7.0, 1.4 Hz, 1H), 6.64 (s, 1H), 3.72 (t, J=5.4 Hz, 4H), 3.68 (t, J=5.2 Hz, 2H), 3.58 (t, J=5.0 Hz, 2H), 3.39 (s, 3H), 1.72 (t, J=4.7 Hz, 2H), 1.67 (s, 4H). MS(ESI, LR) Calculated for C23H27N4O3 [M+H]+: 407.2, found: 407.2. 31 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (t, J=1.8 Hz, 1H), 8.04 (s, 1H), 8.00 (dt, J=7.8, 1.4 Hz, 1H), 7.98-7.88 (m, 2H), 7.59 (t, J=7.8 Hz, 1H), 7.38 (dd, J=8.9, 7.0 Hz, 1H), 6.99 (dd, J=7.0, 1.4 Hz, 1H), 3.69 (t, J=5.3 Hz, 4H), 3.60 (qt, J=5.5 Hz, 2H), 2.76 (t, J=5.7 Hz, 2H), 2.45 (s, 6H), 1.80-1.57 (m, 6H). MS(ESI, LR) Calculated for C24H30N5O2 [M+H]+: 420.2, found: 420.2. 32 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (t, J=1.9 Hz, 1H), 8.06 (s, 1H), 8.04-7.95 (m, 2H), 7.91 (dt, J=8.0, 1.4 Hz, 1H), 7.61 (t, J=7.8 Hz, 1H), 7.39 (dd, J=8.9, 7.0 Hz, 1H), 6.99 (dd, J=7.0, 1.4 Hz, 1H), 6.32 (s, 1H), 3.72 (t, J=5.3 Hz, 4H), 3.34 (dd, J=7.2, 5.4 Hz, 2H), 1.74-1.67 (m, 6H), 1.06 (dt, J=7.7, 4.4 Hz, 1H), 0.62-0.50 (m, 2H), 0.31-0.26 (m, J=5.0 Hz, 2H). MS(ESI, LR) Calculated for C24H27N4O2 [M+H]+: 403.2, found: 403.2. 33 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.44 (d, J=7.5 Hz, 1H), 8.33 (d, J=2.0 Hz, 1H), 8.25 (s, 1H), 8.07 (d, J=7.7 Hz, 1H), 8.01 (d, J=7.8 Hz, 1H), 7.92 (d, J=8.9 Hz, 1H), 7.66 (t, J=7.8 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.23 (d, J=7.0 Hz, 1H), 3.91 (s, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.36-3.31 (m, 2H), 3.12 (d, J=23.3 Hz, 2H), 2.46 (s, 3H), 1.98-1.85 (m, 2H), 1.77-1.61 (m, 4H), 1.58 (qt, J=5.7 Hz, 4H). MS(ESI, LR) Calculated for C26H32N5O2 [M+H]+: 446.3, found: 446.2. 35 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.03-7.92 (m, 3H), 7.66-7.52 (m, 2H), 7.43-7.34 (m, 1H), 7.28-7.26 (m, 1H), 6.98 (d, J=7.0 Hz, 1H), 3.72 (t, J=5.3 Hz, 6H), 3.51 (s, 6H), 1.73-1.67 (m, 6H), 1.48 (s, 9H). MS(ESI, LR) Calculated for C29H36N5O4 [M+H]+: 518.3, found: 518.2. 36 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.97 (t, J=5.6 Hz, 1H), 8.37 (d, J=1.8 Hz, 1H), 8.26 (s, 1H), 8.11 (d, J=7.8 Hz, 1H), 8.02 (d, J=7.8 Hz, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.69 (t, J=7.8 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.24 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.54 (q, J=6.2 Hz, 2H), 2.81 (t, J=6.5 Hz, 2H), 1.66 (d, J=5.7 Hz, 2H), 1.57 (d, J=6.8 Hz, 4H). MS(ESI, LR) Calculated for C23H24N5O2 [M+H]+: 402.2, found: 402.2. 37 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.55 (s, 1H), 8.94 (d, J=2.6 Hz, 1H), 8.51 (t, J=1.7 Hz, 1H), 8.34 (dd, J=4.7, 1.5 Hz, 1H), 8.27 (s, 1H), 8.24-8.09 (m, 3H), 7.93 (dd, J=8.9, 1.3 Hz, 1H), 7.75 (t, J=7.8 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.42 (dd, J=8.3, 4.7 Hz, 1H), 7.30 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=6.4 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C25H24N5O2 [M+H]+: 426.2, found: 426.1. 38 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.00 (s, 1H), 8.52 (d, J=5.5 Hz, 2H), 8.39 (t, J=1.8 Hz, 1H), 8.11-7.89 (m, 4H), 7.72-7.58 (m, 3H), 7.35 (dd, J=8.9, 7.0 Hz, 1H), 6.96 (dd, J=7.1, 1.4 Hz, 1H), 3.69 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.7 Hz, 6H). MS(ESI, LR) Calculated for C25H24N5O2 [M+H]+: 426.2, found: 426.2.

[0661] Example 34. piperazin-1-yl(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0662] <Diagram 4>

[0663]

[0664] Compound 35 (0.1 g, 0.19 mmol) was dissolved in dichloromethane (1 mL) and stirred at 0°C for 10 minutes. 1,4-dioxane dissolved in 4 N hydrochloric acid (0.48 mL) was added, and the mixture was stirred at room temperature for 16 hours. After completion of the reaction, the reaction solution was concentrated and separated using column chromatography to obtain the target compound 34 (36 mg, 44%).

[0665] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (s, 1H), 8.07 (d, J=1.7 Hz, 1H), 8.01 (dt, J=7.5, 1.7 Hz, 1H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.71-7.60 (m, 2H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.23 (dd, J=7.0, 1.4 Hz, 1H), 3.76 (s, 4H), 3.62 (t, J=5.5 Hz, 4H), 3.20 (t, J=5.1 Hz, 4H), 1.66 (d, J=5.2 Hz, 2H), 1.57 (s, 4H).

[0666] MS(ESI, LR) Calculated for C 24 H 28 N5O2[M+H] + : 418.2, found: 418.2.

[0667] Example 39. (7-(5-(morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0668] <Diagram 5>

[0669]

[0670] Step 39-1: Using compound 1-2 and methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylate, the target compound 39-1 was obtained in the same synthetic method as in Step 1-3 in Example 1.

[0671] Step 39-2: Using compound 39-1 and morpholine, the target compound 39 was obtained in the same synthetic method as in Step 1-2 in Example 1.

[0672] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.15 (d,J=2.2 Hz, 1H), 8.77 (d,J=2.0 Hz, 1H), 8.48 (t,J=2.1 Hz, 1H), 8.27 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd,J=8.9, 7.0 Hz, 1H), 7.36 (dd,J=7.1, 1.4 Hz, 1H), 3.67 (s, 4H), 3.63 (t, J=5.4 Hz, 6H), 3.47 (s, 2H), 1.66 (d,J=5.7 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H).

[0673] MS(ESI, LR) Calculated for C 23 H 26 N5O3[M+H] + : 420.2, found: 420.2.

[0674] Example 40. N-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0675] Example 41. Azetidin-1-yl(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0676] Example 42. (3-hydroxyazetidin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0677] Example 43. (7-(5-(2-azaspiro[3,3]heptan-2-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0678] Example 44. (3,3-Difluoroazetidin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0679] Example 45. N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0680] Example 46.N-(cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0681] Example 47. N-(1-methylpiperidin-4-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0682] Example 51. N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0683] Example 52. N-(cyanomethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0684] Example 53. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)nicotinamide

[0685] Example 54. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)nicotinamide

[0686] Example 55. N-(isoxazol-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0687] Example 56. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridazin-4-yl)nicotinamide

[0688] Example 57. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(thiazol-5-ylmethyl)nicotinamide

[0689] Example 192. (3-fluoroazetidin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0690] Example 193.N-(1-methyl-1H-pyrazol-3-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0691] Example 201.N-methylsulfonyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide

[0692] Example 203. 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazin-2-one

[0693] Example 204. 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazine-2,6-dione

[0694] Example 225

[0695] Example 226. 2-oxa-7-azaspiro[3,5]nonan-7-yl-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone

[0696] For Examples 40, 41, 42, 43, 44, 45, 46, 47, 51, 52, 53, 54, 55, 56, 57, 192, 193, 201, 203, 204, 225 and 226, compounds were obtained in the same synthetic method as in Step 1-2 in Example 1, using the corresponding compounds and compound 39-1. The structural and spectral data are shown in Table 4 below.

[0697] Table 4 Example Structure 1H NMR MS 40 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.15 (d, J=2.2 Hz, 1H), 8.90 (d, J=5.1 Hz, 1H), 8.58 (dd, J=8.2, 2.2 Hz, 1H), 8.28 (s, 1H), 8.20 (d, J=8.2 Hz, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.87 (d, J=4.8 Hz, 3H), 1.65 (d, J=6.1 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C20H22N5O2 [M+H]+: 364.2, found: 364.2. 41 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.17 (d, J=2.2 Hz, 1H), 8.92 (d, J=2.1 Hz, 1H), 8.62 (t, J=2.2 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.0, 1.4 Hz, 1H), 4.42 (t, J=7.7 Hz, 2H), 4.11 (t, J=7.8 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 2.30 (p, J=7.7 Hz, 2H), 1.66 (q, J=5.9 Hz, 2H), 1.57 (q, J=5.7 Hz, 4H). MS(ESI, LR) Calculated for C22H24N5O2 [M+H]+: 390.2, found: 390.2. 42 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.18 (d, J=2.2 Hz, 1H), 8.92 (d, J=2.0 Hz, 1H), 8.62 (t, J=2.1 Hz, 1H), 8.27 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.0, 1.4 Hz, 1H), 5.82 (s, 1H), 4.57 (d, J=8.4 Hz, 2H), 4.31 (dd, J=10.1, 6.4 Hz, 1H), 4.21-4.11 (m, 1H), 3.85 (dd, J=11.0, 3.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (qt, J=5.8 Hz, 2H), 1.58 (t, J=6.8 Hz, 4H). MS(ESI, LR) Calculated for C22H24N5O3 [M+H]+: 406.2, found: 406.2. 43 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.18 (d, J=2.2 Hz, 1H), 8.92 (d, J=2.1 Hz, 1H), 8.59 (t, J=2.1 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=9.0, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.1, 1.4 Hz, 1H), 4.39 (s, 2H), 4.08 (s, 2H), 3.63 (t, J=5.4 Hz, 4H), 2.18 (t, J=7.6 Hz, 4H), 1.78 (td, J=7.9, 5.9 Hz, 2H), 1.71-1.61 (m, 2H), 1.58 (sq., J=5.7 Hz, 4H). MS(ESI, LR) Calculated for C25H28N5O2 [M+H]+: 430.2, found: 430.2. 44 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.23 (d, J=2.1 Hz, 1H), 8.99 (d, J=2.1 Hz, 1H), 8.67 (t, J=2.2 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=8.9, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 4.93 (s, 2H), 4.56 (s, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.8 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C22H22F2N5O2 [M+H]+: 426.2, found: 426.1. 45 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.16 (d, J=2.2 Hz, 1H), 8.82 (s, 1H), 8.60 (dd, J=8.2, 2.2 Hz, 1H), 8.28 (s, 1H), 8.21 (d, J=8.2 Hz, 1H), 7.96 (dd, J=8.8, 1.4 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.52 (d, J=2.7 Hz, 4H), 3.30 (s, 3H), 1.66 (d, J=5.6 Hz, 2H), 1.57 (d, J=6.6 Hz, 4H). MS(ESI, LR) Calculated for C22H26N5O3 [M+H]+: 408.2, found: 408.1. 46 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.97 (d, J=2.1 Hz, 1H), 8.88 (d, J=2.1 Hz, 1H), 8.63 (t, J=5.6 Hz, 1H), 8.51 (t, J=2.2 Hz, 1H), 8.04 (s, 1H), 7.70 (dd, J=8.9, 1.4 Hz, 1H), 7.32 (dd, J=8.9, 7.0 Hz, 1H), 7.12 (dd, J=7.1, 1.4 Hz, 1H), 3.38 (t, J=5.4 Hz, 4H), 2.95 (t, J=6.2 Hz, 2H), 1.40 (d, J=5.5 Hz, 2H), 1.32 (s, 4H), 0.87-0.75 (m, 1H), 0.29-0.17 (m, 2H), 0.01 (dd, J=4.8, 1.6 Hz, 2H). MS(ESI, LR) Calculated for C23H26N5O2 [M+H]+: 404.2, found: 404.1. 47 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.21 (d, J=2.1 Hz, 1H), 9.11 (d, J=2.1 Hz, 1H), 8.73 (t, J=2.1 Hz, 1H), 8.56 (d, J=7.6 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=9.0, 7.0 Hz, 1H), 7.36 (dd, J=7.1, 1.3 Hz, 1H), 3.87-3.73 (m, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.79 (d, J=11.0 Hz, 2H), 2.19 (d, J=4.9 Hz, 3H), 2.06-1.93 (m, 2H), 1.88-1.77 (m, 2H), 1.65 (dd, J=7.9, 4.3 Hz, 2H), 1.57 (sq., J=7.6 Hz, 6H). MS(ESI, LR) Calculated for C25H31N6O2 [M+H]+: 447.2, found: 447.2. 51 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.25 (d, J=2.2 Hz, 1H), 9.22-9.12 (m, 2H), 8.78 (t, J=2.1 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.0, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.57 (q, J=6.3 Hz, 2H), 2.82 (t, J=6.5 Hz, 2H), 1.66 (d, J=5.3 Hz, 2H), 1.57 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C22H23N6O2 [M+H]+: 403.2, found: 403.1. 52 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.55 (s, 1H), 9.28 (d, J=2.1 Hz, 1H), 9.14 (d, J=2.1 Hz, 1H), 8.82 (t, J=2.2 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.39 (dd, J=7.1, 1.4 Hz, 1H), 4.41 (d, J=4.3 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.7 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C21H21N6O2 [M+H]+: 389.2, found: 389.1. 53 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.73 (s, 1H), 9.32 (d, J=2.1 Hz, 1H), 9.26 (d, J=2.1 Hz, 1H), 8.95 (d, J=2.5 Hz, 1H), 8.90 (t, J=2.2 Hz, 1H), 8.36 (dd, J=4.7, 1.5 Hz, 1H), 8.30 (s, 1H), 8.21 (dt, J=8.4, 1.9 Hz, 1H), 7.97 (dd, J=8.9, 1.3 Hz, 1H), 7.59 (dd, J=8.9, 7.0 Hz, 1H), 7.48-7.39 (m, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=4.9 Hz, 2H), 1.58 (q, J=5.8 Hz, 4H). MS(ESI, LR) Calculated for C24H23N6O2 [M+H]+: 427.2, found: 427.1. 54 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.17 (s, 1H), 9.15 (d, J=2.1 Hz, 1H), 8.64-8.57 (m, 2H), 8.53 (dd, J=8.2, 2.1 Hz, 1H), 8.46 (d, J=8.2 Hz, 1H), 8.12-8.05 (m, 2H), 7.77-7.71 (m, 2H), 7.43 (dd, J=9.0, 7.0 Hz, 1H), 7.07 (dd, J=7.0, 1.4 Hz, 1H), 3.73 (t, J=5.3 Hz, 4H), 1.79-1.72 (m, 2H), 1.69 (s, 4H). MS(ESI, LR) Calculated for C24H23N6O2 [M+H]+: 427.2, found: 427.1. 55 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.41 (t, J=5.9 Hz, 1H), 9.26 (d, J=2.1 Hz, 1H), 9.16 (d, J=2.1 Hz, 1H), 8.87 (d, J=1.7 Hz, 1H), 8.80 (t, J=2.1 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 6.62-6.55 (m, 1H), 4.62 (d, J=5.8 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.6 Hz, 2H), 1.58 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C23H23N6O3 [M+H]+: 431.2, found: 431.1. 56 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.10 (s, 1H), 9.52 (d, J=2.7 Hz, 1H), 9.35 (d, J=2.1 Hz, 1H), 9.27 (d, J=2.1 Hz, 1H), 9.14 (d, J=5.9 Hz, 1H), 8.91 (t, J=2.1 Hz, 1H), 8.30 (s, 1H), 8.12 (dd, J=5.9, 2.7 Hz, 1H), 7.98 (dd, J=8.9, 1.3 Hz, 1H), 7.59 (dd, J=8.9, 7.0 Hz, 1H), 7.42 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.73-1.63 (m, 2H), 1.58 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C23H22N7O2 [M+H]+: 428.2, found: 428.1. 57 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.49 (t, J=5.7 Hz, 1H), 9.24 (d, J=2.1 Hz, 1H), 9.14 (d, J=2.1 Hz, 1H), 9.00 (s, 1H), 8.78 (t, J=2.2 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.87 (s, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.1, 1.4 Hz, 1H), 4.75 (d, J=5.7 Hz, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.71-1.61 (m, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C23H23N6O2S [M+H]+: 447.2, found: 447.1. 192 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.20 (d, J=2.2 Hz, 1H), 8.95 (d, J=2.1 Hz, 1H), 8.64 (t, J=2.1 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.0, 1.4 Hz, 1H), 5.48 (ddt, J=57.6, 6.1, 2.9 Hz, 1H), 4.72-4.42 (m, 3H), 4.16 (dd, J=24.6, 11.8 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.57 (d, J=7.7 Hz, 4H). MS(ESI, LR) Calculated for C22H23FN5O2 [M+H]+: 408.1, found: 408.1. 193 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.22 (s, 1H), 9.31 (d, J=2.1 Hz, 1H), 9.22 (d, J=2.1 Hz, 1H), 8.92 (t, J=2.2 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=9.0, 1.4 Hz, 1H), 7.65 (d, J=2.2 Hz, 1H), 7.58 (dd, J=8.9, 7.0 Hz, 1H), 7.42 (dd, J=7.1, 1.3 Hz, 1H), 6.64 (d, J=2.2 Hz, 1H), 3.80 (s, 3H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=6.9 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C23H24N7O2 [M+H]+: 430.1, found: 430.1. 201 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.49 (s, 1H), 9.36 (d, J=2.1 Hz, 1H), 9.18 (d, J=2.1 Hz, 1H), 8.88 (t, J=2.1 Hz, 1H), 8.30 (s, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.58 (dd, J=8.9, 7.0 Hz, 1H), 7.40 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.41 (s, 3H), 1.70-1.62 (m, 2H), 1.57 (t, J=6.1 Hz, 4H). MS(ESI, LR) Calculated for C20H22N5O4S [M+H]+: 428.1, found: 428.1. 203 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.11 (d, J=2.2 Hz, 1H), 8.84 (d, J=2.1 Hz, 1H), 8.52 (t, J=2.1 Hz, 1H), 8.11-7.98 (m, 2H), 7.41 (dd, J=9.0, 7.0 Hz, 1H), 7.06 (dd, J=7.0, 1.4 Hz, 1H), 6.34 (s, 1H), 4.38 (s, 2H), 3.90 (s, 2H), 3.72 (t, J=5.3 Hz, 4H), 3.54 (s, 2H), 1.74 (s, 2H), 1.67 (d, J=6.5 Hz, 4H). MS(ESI, LR) Calculated for C23H25N6O3[M+H]+: 433.2, found: 433.2. 204 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.48 (s, 1H), 9.19 (d, J=2.1 Hz, 1H), 8.82 (d, J=2.1 Hz, 1H), 8.54 (t, J=2.1 Hz, 1H), 8.26 (s, 1H), 7.95 (dd, J=8.9, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 4.41 (s, 4H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=6.5 Hz, 2H), 1.57 (d, J=7.3 Hz, 4H). MS(ESI, LR) Calculated for C23H23N6O4[M+H]+: 447.2, found: 447.1. 225 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.18 (t, J=1.6 Hz, 1H), 8.91 (t, J=1.8 Hz, 1H), 8.58 (q, J=2.2 Hz, 1H), 8.28 (s, 1H), 7.94 (dd, J=9.0, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.35 (dd, J=7.0, 1.4 Hz, 1H), 5.04 (d, J=6.0 Hz, 1H), 4.36 (d, J=17.6 Hz, 2H), 4.06 (d, J=21.1 Hz, 2H), 3.96 (dq., J=20.5, 6.8 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.47 (td, J=6.7, 3.4 Hz, 2H), 1.99 (s, 2H), 1.66 (d, J=5.7 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C25H28N5O3[M+H]+: 446.2, found: 446.1. 226 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.14 (d, J=2.2 Hz, 1H), 8.73 (d, J=2.0 Hz, 1H), 8.44 (t, J=2.1 Hz, 1H), 8.27 (s, 1H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.1, 1.4 Hz, 1H), 4.35 (d, J=5.7 Hz, 4H), 3.73-3.51 (m, 6H), 3.36 (s, 2H), 1.86 (s, 4H), 1.65 (d, J=6.3 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C26H30N5O3[M+H]+: 460.2, found: 460.1.

[0698] Example 48. piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0699] Example 200.N-(azetidin-3-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0700] The target compound was obtained by successively using the same synthetic method as in Step 1-2 of Example 1 and the synthetic method of Example 34 using the corresponding compounds and compound 39-1. The structural and spectral data are shown in Table 5 below.

[0701] Table 5 Example Structure 1H NMR MS 48 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.17 (d, J=2.1 Hz, 1H), 8.81 (d, J=2.0 Hz, 1H), 8.54 (t, J=2.1 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (t, J=5.5 Hz, 8H), 3.20 (t, J=5.3 Hz, 4H), 1.66 (q, J=5.9 Hz, 2H), 1.57 (q, J=5.8 Hz, 4H). MS(ESI, LR) Calculated for C23H28N6O2 [M+H]+: 419.2, found: 419.1. 200 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.61 (d, J=6.6 Hz, 1H), 9.27 (d, J=2.1 Hz, 1H), 9.19 (d, J=2.1 Hz, 1H), 9.05 (s, 2H), 8.82 (t, J=2.1 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.39 (dd, J=7.0, 1.4 Hz, 1H), 4.88 (h, J=7.6 Hz, 1H), 4.26-4.09 (m, 4H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=6.8 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H25N6O2 [M+H]+: 405.2, found: 405.1.

[0702] Example 49. (4-methylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0703] <Diagram 6>

[0704]

[0705] Compound 48 (50 mg, 0.12 mmol) was dissolved in ethyl alcohol (0.6 mL) and water (0.6 mL), 37% formaldehyde solution (17.8 μL, 0.24 mmol) was added, and the mixture was stirred at 60 °C for 1 hour. Sodium cyanoborohydride (15 mg, 0.24 mmol) and acetic acid (6.8 μL, 0.12 mmol) were added to the reaction solution, and the mixture was stirred at 60 °C for 12 hours. The reaction solution was concentrated and separated using column chromatography to obtain the target compound 49 (30 mg, 57%).

[0706] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.14 (d,J=2.1 Hz, 1H), 8.74 (d,J=2.0 Hz, 1H), 8.45 (t,J=2.1 Hz, 1H), 8.27 (s, 1H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd,J=8.9, 7.0 Hz, 1H), 7.36 (dd,J=7.0, 1.4 Hz, 1H), 3.64 (sq.,J=8.5 Hz, 6H), 3.44 (s, 2H), 2.37 (d,J=19.9 Hz, 4H), 2.21 (s, 3H), 1.65 (d, J=5.5 Hz, 2H), 1.57 (d, J=7.2 Hz, 4H).

[0707] MS(ESI, LR) Calculated for C 24 H 29 N6O2[M+H] + : 433.2, found: 433.1.

[0708] Example 202.N-(1-methylazetidin-3-yl)-5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-3-carboxamide

[0709]

[0710] Using compound 200 and corresponding compounds, target compound 202 was obtained using the same synthesis method as in Example 49.

[0711] 1 H NMR (400 MHz, DMSO-d6) δ(m.d.): 9.68-9.54 (m, 1H), 9.26 (t,J=2.4 Hz, 1H), 9.18 (d,J=5.6 Hz, 1H), 8.81 (t,J=2.8 Hz, 1H), 8.81 (t,J=2.8 Hz, 7.39-Hz). (m, 1H), 7.56 (dd,J=8.9, 7.0 Hz, 1H), 7.38 (dd,J=7.1, 2.9 Hz, 1H), 4.49 (s, 1H), 4.16 (dt,J=18.1, 8.5 Hz, 2H), t 3.62,J=8.4, Hz, 2.89 (d,J=5.5 Hz, 4H), 2.73 (s, 1H), 1.65 (sq.,J=5.6 Hz, 2H), 1.60-1.51 (m, 4H).

[0712] MS(ESI, LR) Calculated for C 23 H 27 N6O2[M+H] + : 419.1, found: 419.1.

[0713] Example 50. (4-isopropylpiperazin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0714]

[0715] Using compound 48 and acetone, the target compound 50 was obtained in the same synthetic method as used in Example 49.

[0716] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.14 (d, J=2.2 Hz, 1H), 8.75 (d, J=2.1 Hz, 1H), 8.45 (t, J=2.1 Hz, 1H), 8.27 (s, 1H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.36 (dd, J=7.0, 1.3 Hz, 1H), 3.63 (t, J=5.5 Hz, 6H), 3.42 (s, 2H), 2.70 (p, J=6.5 Hz, 1H), 2.49 (d, J=12.9 Hz, 4H), 1.65 (d, J=5.1 Hz, 2H), 1.57 (s, 4H), 0.98 (d, J=6.5 Hz, 6H).

[0717] MS(ESI, LR) Calculated for C 26 H 33 N6O2[M+H] + : 461.3, found: 461.2.

[0718] Example 58. N-methyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0719] Example 59.N,N-dimethyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0720] Example 60.N-isopropyl-4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0721] Example 61. azetidin-1-yl(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0722] Example 62.N-(2-methoxyethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0723] Example 63. N-(2-(dimethylamino)ethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0724] Example 64. N-(cyclopropylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0725] Example 65. N-(1-methylpiperidin-4-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0726] Example 69. N-(2-cyanoethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0727] Example 70. N-(cyanomethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0728] Example 71. 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide

[0729] Example 72. 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide

[0730] Example 73. N-(isoxazol-3-ylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0731] For Examples 58, 59, 60, 61, 62, 63, 64, 65, 69, 70, 71, 72 and 73, compounds were obtained in the same synthetic method as in Step 1-2 in Example 1, using the corresponding compounds and compound 10. The structural and spectral data are shown in Table 6 below.

[0732] Table 6 Example Structure 1H NMR MS 58 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.59 (d, J=4.8 Hz, 1H), 8.25 (s, 1H), 8.01 (q, J=8.6 Hz, 4H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.24 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.84 (d, J=4.5 Hz, 3H), 1.71-1.61 (m, 2H), 1.57 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C21H23N4O2 [M+H]+: 363.2, found: 363.2. 59 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (s, 1H), 8.04-7.97 (m, 2H), 7.90 (dd, J=8.9, 1.3 Hz, 1H), 7.62-7.56 (m, 2H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.23 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.01 (d, J=17.6 Hz, 6H), 1.65 (d, J=5.5 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H25N4O2 [M+H]+: 377.2, found: 377.3. 60 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.05 (s, 1H), 7.99 (dd, J=8.9, 1.4 Hz, 1H), 7.96-7.86 (m, 4H), 7.38 (dd, J=8.9, 7.0 Hz, 1H), 6.97 (dd, J=7.0, 1.4 Hz, 1H), 5.98 (d, J=7.8 Hz, 1H), 4.32 (dq, J=13.4, 6.7 Hz, 1H), 3.72 (t, J=5.3 Hz, 4H), 1.73-1.65 (m, 6H), 1.29 (d, J=6.5 Hz, 6H). MS(ESI, LR) Calculated for C23H27N4O2 [M+H]+: 391.2, found: 391.2. 61 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (s, 1H), 8.06-7.98 (m, 2H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.84-7.74 (m, 2H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.23 (dd, J=7.1, 1.4 Hz, 1H), 4.38 (t, J=7.7 Hz, 2H), 4.10 (t, J=7.8 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 2.30 (p, J=7.7 Hz, 2H), 1.72-1.61 (m, 2H), 1.57 (sq., J=6.0 Hz, 4H). MS(ESI, LR) Calculated for C23H25N4O2 [M+H]+: 389.2, found: 389.2. 62 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.68 (d, J=6.3 Hz, 1H), 8.25 (s, 1H), 8.09-7.97 (m, 4H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.24 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.57-3.44 (m, 4H), 3.30 (s, 3H), 1.65 (d, J=5.4 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C23H27N4O3 [M+H]+: 407.2, found: 407.2. 63 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.53 (s, 1H), 8.25 (s, 1H), 8.01 (q, J=8.6 Hz, 4H), 7.91 (dd, J=8.9, 1.3 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.23 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.5 Hz, 4H), 3.40 (q, J=6.5 Hz, 2H), 2.44 (t, J=6.9 Hz, 2H), 2.20 (s, 6H), 1.65 (d, J=6.5 Hz, 2H), 1.57 (d, J=6.9 Hz, 4H). MS(ESI, LR) Calculated for C24H30N5O2 [M+H]+: 420.2, found: 420.2. 64 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.06 (s, 1H), 7.99 (dd, J=8.9, 1.4 Hz, 1H), 7.94 (s, 4H), 7.39 (dd, J=8.9, 7.0 Hz, 1H), 6.98 (dd, J=7.0, 1.4 Hz, 1H), 6.27 (s, 1H), 3.72 (t, J=5.4 Hz, 4H), 3.36 (dd, J=7.2, 5.3 Hz, 2H), 1.73-1.66 (m, 6H), 1.09 (ddd, J=12.6, 7.8, 4.9 Hz, 1H), 0.63-0.53 (m, 2H), 0.35-0.24 (m, 2H). MS(ESI, LR) Calculated for C24H27N4O2 [M+H]+: 403.2, found: 403.2. 65 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.38 (d, J=7.7 Hz, 1H), 8.25 (s, 1H), 8.06-7.96 (m, 4H), 7.91 (dd, J=8.9, 1.3 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.22 (dd, J=7.2, 1.4 Hz, 1H), 3.83-3.71 (m, 1H), 3.62 (t, J=5.4 Hz, 4H), 2.79 (d, J=11.0 Hz, 2H), 2.18 (s, 3H), 1.96 (dd, J=12.8, 10.3 Hz, 2H), 1.79 (d, J=12.3 Hz, 2H), 1.70-1.53 ​​(m, 8H). MS(ESI, LR) Calculated for C26H32N5O2 [M+H]+: 446.3, found: 446.2. 69 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.00 (t, J=5.7 Hz, 1H), 8.25 (s, 1H), 8.07 (d, J=8.3 Hz, 2H), 8.02 (d, J=8.5 Hz, 2H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.54 (dd, J=8.9, 7.1 Hz, 1H), 7.25 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.55 (q, J=6.3 Hz, 2H), 2.83 (t, J=6.5 Hz, 2H), 1.65 (d, J=8.1 Hz, 2H), 1.57 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C23H24N5O2 [M+H]+: 402.2, found: 402.1. 70 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.36 (t, J=5.4 Hz, 1H), 8.25 (s, 1H), 8.08 (d, J=8.5 Hz, 2H), 8.03 (d, J=8.3 Hz, 2H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.25 (dd, J=7.1, 1.4 Hz, 1H), 4.37 (d, J=5.4 Hz, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.3 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H22N5O2 [M+H]+: 388.2, found: 388.1. 71 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.61 (s, 1H), 8.98 (d, J=2.5 Hz, 1H), 8.35 (dd, J=4.7, 1.5 Hz, 1H), 8.30-8.21 (m, 2H), 8.19-8.06 (m, 4H), 7.93 (dd, J=8.9, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.43 (dd, J=8.3, 4.7 Hz, 1H), 7.28 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=6.6 Hz, 2H), 1.58 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C25H24N5O2 [M+H]+: 426.2, found: 426.1. 72 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.75 (s, 1H), 8.57-8.48 (m, 2H), 8.27 (s, 1H), 8.13 (s, 4H), 7.93 (dd, J=8.9, 1.3 Hz, 1H), 7.88-7.79 (m, 2H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.28 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.8 Hz, 2H), 1.62-1.49 (m, 4H). MS(ESI, LR) Calculated for C25H24N5O2 [M+H]+: 426.2, found: 426.2. 73 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.26 (t, J=5.8 Hz, 1H), 8.87 (d, J=1.7 Hz, 1H), 8.25 (s, 1H), 8.05 (s, 4H), 7.91 (dd, J=8.8, 1.4 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.24 (dd, J=7.1, 1.4 Hz, 1H), 6.55 (d, J=1.7 Hz, 1H), 4.61 (d, J=5.9 Hz, 2H), 3.63 (t, J=5.5 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C24H24N5O3 [M+H]+: 430.2, found: 430.2.

[0733] Example 66. piperazin-1-yl(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0734]

[0735] Using compound 10 and 1-Boc-piperazine, the target compound 66 was obtained by successively using the synthetic method of Step 1-2 in Example 1 and the synthetic method of Example 34.

[0736] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.24 (s, 1H), 8.03 (d, J=8.1 Hz, 2H), 7.90 (dd, J=8.9, 1.3 Hz, 1H), 7.65 (d, J=8.3 Hz, 2H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.22 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 8H), 3.18 (s, 4H), 1.66 (d, J=5.8 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H).

[0737] MS(ESI, LR) Calculated for C 24 H 28 N5O2[M+H] + : 418.2, found: 418.1.

[0738] Example 67. (4-methylpiperazin-1-yl)(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0739] Example 68 (4-isopropylpiperazin-1-yl)(4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0740] For Examples 67 and 68, compounds were obtained in the same synthetic method as in Example 49 using the corresponding compounds and compound 66. The structural and spectral data are shown in Table 7 below.

[0741] Table 7 Example Structure 1H NMR MS 67 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.24 (s, 1H), 8.06-7.96 (m, 2H), 7.90 (dd, J=8.9, 1.3 Hz, 1H), 7.63-7.48 (m, 3H), 7.22 (dd, J=7.0, 1.3 Hz, 1H), 3.62 (t, J=5.3 Hz, 8H), 2.36 (d, J=19.6 Hz, 4H), 2.22 (s, 3H), 1.70-1.62 (m, 2H), 1.57 (d, J=6.9 Hz, 4H). MS(ESI, LR) Calculated for C25H30N5O2 [M+H]+: 432.2, found: 432.1. 68 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.24 (s, 1H), 8.05-7.96 (m, 2H), 7.90 (dd, J=8.9, 1.3 Hz, 1H), 7.54 (dd, J=16.2, 8.6 Hz, 3H), 7.22 (dd, J=7.1, 1.4 Hz, 1H), 3.74-3.54 (m, 6H), 3.41 (s, 2H), 2.70 (p, J=6.5 Hz, 1H), 2.51-2.35 (m, 4H), 1.65 (d, J=5.8 Hz, 2H), 1.57 (d, J=7.2 Hz, 4H), 0.99 (d, J=6.5 Hz, 6H). MS(ESI, LR) Calculated for C27H34N5O2 [M+H]+: 460.3, found: 460.2.

[0742] Example 74. (7-(6-(morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0743] <Diagram 7>

[0744]

[0745] Using compound 1-2 and methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate, the target compound 74 was obtained by the same synthetic method as in Example 39.

[0746] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.15 (d, J=2.1 Hz, 1H), 8.77 (d, J=2.0 Hz, 1H), 8.48 (t, J=2.1 Hz, 1H), 8.27 (s, 1H), 7.95 (dd, J=9.0, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.0, 1.4 Hz, 1H), 3.64 (q, J=9.3 Hz, 10H), 3.46 (s, 2H), 1.72-1.61 (m, 2H), 1.58 (t, J=6.5 Hz, 4H).

[0747] MS(ESI, LR) Calculated for C 23 H 26 N5O3[M+H] + : 420.2, found: 420.1.

[0748] Example 75.N-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0749] Example 76.N-isopropyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0750] Example 77. azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0751] Example 78.N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0752] Example 79. N-(2-(dimethylamino)ethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0753] Example 80.N-(cyclopropylmethyl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0754] Example 81. N-(1-methylpiperidin-4-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0755] Example 85. N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0756] Example 86. N-(cyanomethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0757] Example 87. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)picolinamide

[0758] Example 88. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)picolinamide

[0759] Example 89. N-(isoxazol-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0760] Example 213. (3-fluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone

[0761] Example 214. 2-azaspiro[3,3]heptan-2-yl-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone

[0762] Example 237. (3,3-difluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone

[0763] For Examples 75, 76, 77, 78, 79, 80, 81, 85, 86, 87, 88, 89, 213, 214 and 237, compounds were obtained in the same synthetic method as in Step 1-2 in Example 1, using the corresponding compounds and compound 74-1. The structural and spectral data are shown in Table 8 below.

[0764] Table 8 Example Structure 1H NMR MS 75 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.22 (d, J=2.1 Hz, 1H), 9.10 (d, J=2.1 Hz, 1H), 8.81-8.70 (m, 2H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.85 (d, J=4.5 Hz, 3H), 1.65 (d, J=6.2 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C20H22N5O2 [M+H]+: 364.2, found: 364.2. 76 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.20 (d, J=2.1 Hz, 1H), 9.11 (d, J=2.1 Hz, 1H), 8.73 (t, J=2.1 Hz, 1H), 8.53 (d, J=7.6 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.0, 1.3 Hz, 1H), 4.14 (dq, J=13.4, 6.6 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=6.5 Hz, 2H), 1.57 (s, 4H), 1.20 (d, J=6.6 Hz, 6H). MS(ESI, LR) Calculated for C22H26N5O2 [M+H]+: 392.2, found: 392.2. 77 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.17 (d, J=2.2 Hz, 1H), 8.92 (d, J=2.1 Hz, 1H), 8.62 (t, J=2.1 Hz, 1H), 8.27 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.36 (dd, J=7.1, 1.4 Hz, 1H), 4.42 (t, J=7.7 Hz, 2H), 4.11 (t, J=7.8 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 2.30 (p, J=7.6 Hz, 2H), 1.65 (d, J=5.4 Hz, 2H), 1.57 (d, J=6.4 Hz, 4H). MS(ESI, LR) Calculated for C22H24N5O2 [M+H]+: 390.2, found: 390.1. 78 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.22 (d, J=2.1 Hz, 1H), 9.12 (d, J=2.1 Hz, 1H), 8.86 (s, 1H), 8.76 (t, J=2.2 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.1 Hz, 1H), 7.36 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.49 (sq., J=2.8 Hz, 4H), 3.29 (s, 3H), 1.71-1.61 (m, 2H), 1.57 (d, J=7.3 Hz, 4H). MS(ESI, LR) Calculated for C22H26N5O3 [M+H]+: 408.2, found: 408.2. 79 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.22 (d, J=2.1 Hz, 1H), 9.11 (d, J=2.1 Hz, 1H), 8.79-8.67 (m, 2H), 8.29 (s, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.41 (q, J=6.5 Hz, 2H), 2.43 (t, J=6.8 Hz, 2H), 2.19 (s, 6H), 1.66 (d, J=6.4 Hz, 2H), 1.57 (d, J=6.6 Hz, 4H). MS(ESI, LR) Calculated for C23H29N6O2 [M+H]+: 421.2, found: 421.2. 80 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.22 (d, J=2.1 Hz, 1H), 9.13 (d, J=2.1 Hz, 1H), 8.88 (t, J=5.6 Hz, 1H), 8.77 (t, J=2.1 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.20 (t, J=6.2 Hz, 2H), 1.66 (d, J=5.4 Hz, 2H), 1.58 (d, J=4.4 Hz, 4H), 1.12-1.00 (m, 1H), 0.51-0.42 (m, 2H), 0.30-0.21 (m, 2H). MS(ESI, LR) Calculated for C23H26N5O2 [M+H]+: 404.2, found: 404.2. 81 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.20-9.12 (m, 1H), 8.66 (d, J=8.4 Hz, 1H), 8.58 (dd, J=8.2, 2.2 Hz, 1H), 8.27 (s, 1H), 8.23-8.14 (m, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=7.0, 1.4 Hz, 1H), 3.80 (dd, J=9.4, 4.9 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.76 (d, J=11.2 Hz, 2H), 2.18 (s, 3H), 1.99 (t, J=11.0 Hz, 2H), 1.74 (dt, J=14.0, 10.0 Hz, 4H), 1.65 (d, J=6.1 Hz, 2H), 1.62-1.51 (m, 4H). MS(ESI, LR) Calculated for C25H31N6O2 [M+H]+: 447.2, found: 447.3. 85 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.25 (d, J=2.1 Hz, 1H), 9.17 (t, J=5.6 Hz, 1H), 9.14 (d, J=2.1 Hz, 1H), 8.78 (t, J=2.1 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.57 (sq., J=6.2 Hz, 2H), 2.82 (t, J=6.5 Hz, 2H), 1.66 (d, J=5.5 Hz, 2H), 1.62-1.52 (m, 4H). MS(ESI, LR) Calculated for C22H23N6O2 [M+H]+: 403.2, found: 403.2. 86 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.54 (s, 1H), 9.28 (d, J=2.1 Hz, 1H), 9.14 (d, J=2.1 Hz, 1H), 8.81 (t, J=2.1 Hz, 1H), 8.29 (s, 1H), 7.96 (dd, J=9.0, 1.4 Hz, 1H), 7.57 (dd, J=8.9, 7.1 Hz, 1H), 7.38 (dd, J=7.0, 1.4 Hz, 1H), 4.41 (d, J=4.6 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.7 Hz, 2H), 1.57 (d, J=6.8 Hz, 4H). MS(ESI, LR) Calculated for C21H21N6O2 [M+H]+: 389.2, found: 389.1. 87 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.74 (s, 1H), 9.29 (dd, J=22.2, 2.1 Hz, 2H), 8.99-8.87 (m, 2H), 8.37 (dd, J=4.7, 1.5 Hz, 1H), 8.30 (s, 1H), 8.22 (dt, J=8.5, 2.0 Hz, 1H), 7.97 (dd, J=8.9, 1.3 Hz, 1H), 7.59 (dd, J=8.9, 7.0 Hz, 1H), 7.44 (td, J=8.1, 3.0 Hz, 2H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=7.1 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C24H23N6O2 [M+H]+: 427.2, found: 427.1. 88 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.86 (s, 1H), 9.32 (d, J=2.1 Hz, 1H), 9.24 (d, J=2.1 Hz, 1H), 8.88 (t, J=2.2 Hz, 1H), 8.58-8.48 (m, 2H), 8.30 (s, 1H), 7.97 (dd, J=8.9, 1.4 Hz, 1H), 7.84-7.74 (m, 2H), 7.58 (dd, J=8.9, 7.0 Hz, 1H), 7.42 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=6.0 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C24H23N6O2 [M+H]+: 427.2, found: 427.1. 89 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.42 (t, J=5.9 Hz, 1H), 9.26 (d, J=2.1 Hz, 1H), 9.16 (d, J=2.1 Hz, 1H), 8.87 (d, J=1.7 Hz, 1H), 8.80 (t, J=2.1 Hz, 1H), 8.29 (s, 1H), 7.95 (dd, J=8.9, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 6.58 (d, J=1.7 Hz, 1H), 4.62 (d, J=5.8 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.8 Hz, 2H), 1.56 (t, J=5.8 Hz, 4H). MS(ESI, LR) Calculated for C23H23N6O3 [M+H]+: 431.2, found: 431.1. 213 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.18 (t, J=1.6 Hz, 1H), 8.91 (t, J=1.8 Hz, 1H), 8.58 (q, J=2.2 Hz, 1H), 8.28 (s, 1H), 7.94 (dd, J=9.0, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.35 (dd, J=7.0, 1.4 Hz, 1H), 5.04 (d, J=6.0 Hz, 1H), 4.36 (d, J=17.6 Hz, 2H), 4.06 (d, J=21.1 Hz, 2H), 3.96 (dq., J=20.5, 6.8 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.47 (td, J=6.7, 3.4 Hz, 2H), 1.99 (s, 2H), 1.66 (d, J=5.7 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H23FN5O2 [M+H]+: 408.2, found: 408.1. 214 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.14 (d, J=2.2 Hz, 1H), 8.54 (dd, J=8.2, 2.3 Hz, 1H), 8.27 (s, 1H), 8.11 (d, J=8.2 Hz, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.35 (dd, J=7.0, 1.4 Hz, 1H), 4.62 (s, 2H), 4.09 (s, 2H), 3.63 (t, J=5.4 Hz, 4H), 2.19 (t, J=7.6 Hz, 4H), 1.86-1.75 (m, 2H), 1.66 (t, J=5.7 Hz, 2H), 1.57 (d, J=6.3 Hz, 4H). MS(ESI, LR) Calculated for C25H28N5O2 [M+H]+: 430.2, found: 430.2. 237 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.19 (d, J=2.2 Hz, 1H), 8.59 (dd, J=8.2, 2.2 Hz, 1H), 8.28 (s, 1H), 8.20 (d, J=8.3 Hz, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.66-7.62 (m, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 5.09 (t, J=12.5 Hz, 2H), 4.57 (t, J=12.5 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.8 Hz, 2H), 1.57 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C22H22F2N5O2 [M+H]+: 426.2, found: 426.1.

[0765] Example 82. piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0766]

[0767] With the use of compound74-1and 1-Boc-piperazine, the target compound82was obtained by successively using the step 1-2 synthesis method in Example 1 and the synthesis method of Example 34.

[0768] 1 H NMR (400 MHz, DMSO-d6) δ(m.d.): 9.13 (d,J=2.1 Hz, 1H), 9.02 (s, 2H), 8.56 (dd,J=8.1, 2.2 Hz, 1H), 8.27 (d,J=8.1, 2.2 Hz, 1H), 8.27 (s, 1H, 7,95), ,J=1,9 Hz, 1H), 7.87 (d,J=8.2 Hz, 1H), 7.57 (dd,J=8.9, 7.1 Hz, 1H), 7.35 (dd,J=7.1, 1.4 Hz, 1H), 3.91 (d,J=5.6 Hz, 2H, 78), ,J=6.2 Hz, 3.63 (t,J=5.4 Hz, 4H), 3.21 (d,J=6.3 Hz, 2H), 3.18-3.08 (m, 2H), 1.66 (sq.,J=5.6 Hz, 2H), 1.58 (sq.,J=5.5 Hz, 4H).

[0769] MS(ESI, LR) Calculated for C 23 H 27 N6O2[M+H] + : 419.2, found: 419.1.

[0770] Example 83. (4-methylpiperazin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0771] Example 84. (4-isopropylpiperazin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0772] For Examples 83 and 84, the compounds were prepared in the same synthetic method as in Example 49 using the corresponding compounds and compound 74-1. The structural and spectral data are shown in Table 9 below.

[0773] Table 9 Example Structure 1H NMR MS 83 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.10 (dd, J=2.3, 0.9 Hz, 1H), 8.52 (dd, J=8.2, 2.2 Hz, 1H), 8.27 (s, 1H), 7.94 (dd, J=8.9, 1.4 Hz, 1H), 7.76 (dd, J=8.2, 0.9 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.35 (dd, J=7.0, 1.4 Hz, 1H), 3.69 (t, J=5.1 Hz, 2H), 3.63 (t, J=5.5 Hz, 4H), 3.47 (t, J=4.9 Hz, 2H), 2.42 (t, J=5.1 Hz, 2H), 2.33 (t, J=5.0 Hz, 2H), 1.66 (qt, J=6.2 Hz, 2H), 1.57 (p, J=5.3 Hz, 4H). MS(ESI, LR) Calculated for C24H29N6O2 [M+H]+: 433.2, found: 433.1. 84 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.10 (dd, J=2.2, 0.9 Hz, 1H), 8.52 (dd, J=8.2, 2.2 Hz, 1H), 8.27 (s, 1H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.76 (dd, J=8.2, 0.9 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.35 (dd, J=7.1, 1.4 Hz, 1H), 3.67 (t, J=5.0 Hz, 2H), 3.63 (t, J=5.5 Hz, 4H), 3.45 (t, J=4.9 Hz, 2H), 2.71 (p, J=6.5 Hz, 1H), 2.54 (t, J=5.1 Hz, 2H), 2.45 (t, J=5.0 Hz, 2H), 1.65 (d, J=4.9 Hz, 2H), 1.57 (d, J=7.0 Hz, 4H), 0.99 (d, J=6.5 Hz, 6H). MS(ESI, LR) Calculated for C26H33N6O2 [M+H]+: 461.3, found: 461.2.

[0774] Example 243. 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid

[0775] <Pattern 8>

[0776]

[0777] Step 243-1: Using compound 1-2 and (5-fluoro-6-(methoxycarbonyl)pyridin-3-yl)boronic acid, the target compound 243-1 was obtained in the same synthetic method as in Step 1-3 in Example 1.

[0778] Step 243-2: Compound 243-1 (19 mg, 49 μM) was dissolved in tetrahydrofuran (1 mL), 1 N sodium hydroxide solution (0.3 mL) was added, and the mixture was stirred at 0°C for 2 hours. After completion of the reaction, water (3 mL) was added to the reaction solution, and it was washed with dichloromethane solution. The aqueous layer was acidified with 1 N hydrochloric acid solution until the pH of the aqueous solution was adjusted to 2, and then extracted with dichloromethane (5 mL x 3). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain the target compound 243 (12 mg, 66%).

[0779] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 13.82 (s, 1H), 9.07 (d, J=1.6 Hz, 1H), 8.57 (dd, J=11.5, 1.7 Hz, 1H), 8.31 (s, 1H), 7.98 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.1 Hz, 1H), 7.46 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (q, J=5.6 Hz, 2H), 1.57 (q, J=5.7 Hz, 4H).

[0780] MS(ESI, LR) Calculated for C 19 H 18 FN4O3[M+H] +: 369.1, found: 369.1.

[0781] Example 248. [7-[6-(azetidine-1-carbonyl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0782]

[0783] Using compound243and azetidine, the target compound248was obtained by the same synthesis method as in steps 1-2 in Example 1.

[0784] 1 H NMR (400 MHz, DMSO-d6) δ(m.d.): 9.02 (t,J=1.5 Hz, 1H), 8.53 (dd,J=11.2, 1.7 Hz, 1H), 8.30 (s, 1H), 7.97 (dd,J=1.9, G, 1.5 Hz), 7.5 (dd,J=8.9, 7.1 Hz, 1H), 7.43 (dd,J=7.0, 1.3 Hz, 1H), 4.28 (t,J=7.7 Hz, 2H), 4.13 (t,J=7.8 Hz, 2H), 3.63 (t,J=7.4 Hz, 2H), 3.63 (t,J=5.4 Hz, 2H), p Hz, 2H), 1.66 (e,J=5.2 Hz, 2H), 1.57 (e,J=6.7 Hz, 4H).

[0785] MS(ESI, LR) Calculated for C 22 H 23 FN5O2[M+H] + : 408.2, found: 408.1.

[0786] Example 249. [7-[5-fluoro-6-(morpholine-4-carbonyl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0787] Example 250. 3-Fluoro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-2-carboxamide

[0788] For Examples 249 and 250, the target compounds were obtained using the same synthetic method as in Step 1-2 in Example 1, using the corresponding compounds and compound 243. The structural and spectral data are shown in Table 10 below.

[0789] Table 10 Example Structure 1H NMR MS 249 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.03 (t, J=1.6 Hz, 1H), 8.56 (dd, J=10.5, 1.7 Hz, 1H), 8.30 (s, 1H), 7.97 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.1 Hz, 1H), 7.42 (dd, J=7.1, 1.4 Hz, 1H), 3.72 (s, 4H), 3.61 (dt, J=13.6, 5.2 Hz, 6H), 3.35 (d, J=4.9 Hz, 2H), 1.65 (d, J=4.7 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C23H25FN5O3 [M+H]+: 438.2, found: 438.2. 250 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.03 (t, J=1.5 Hz, 1H), 8.78 (d, J=5.1 Hz, 1H), 8.53 (dd, J=11.7, 1.7 Hz, 1H), 8.30 (s, 1H), 7.98 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.1 Hz, 1H), 7.45 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.84 (d, J=4.7 Hz, 3H), 1.66 (d, J=5.7 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C20H21FN5O2 [M+H]+: 382.2, found: 382.1.

[0790] Example 277. [7-[2-(azetidine-1-carbonyl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0791] <Diagram 9>

[0792]

[0793] Compound 277-1 was obtained in the same synthetic method as in Step 1-3 in Example 1 using compound 1-2 and (2-(methoxycarbonyl)pyrimidin-5-yl)boronic acid, and then the target compound 277 was obtained in the same synthetic method as in Step 1-2 in Example 1 using azetidine.

[0794] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.51 (s, 2H), 8.31 (s, 1H), 7.98 (dd, J=8.9, 1.4 Hz, 1H), 7.58 (dd, J=8.9, 7.0 Hz, 1H), 7.48 (dd, J=7.1, 1.4 Hz, 1H), 4.48 (t, J=7.7 Hz, 2H), 4.14 (t, J=7.7 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 2.39-2.27 (m, 2H), 1.66 (d, J=5.4 Hz, 2H), 1.57 (d, J=6.9 Hz, 4H).

[0795] MS(ESI, LR) Calculated for C 21 H 23 N6O2[M+H] + : 391.2, found: 391.1.

[0796] Example 258. 3-chloro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid

[0797]

[0798] The intermediate compound was obtained in the same synthetic method as in Step 1-3 in Example 1 using (5-chloro-6-(methoxycarbonyl)pyridin-3-yl)boronic acid, and then the target compound 258 was obtained in the same synthetic method as in Step 243-2 in Example 243.

[0799] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 14.07 (s, 1H), 9.08 (d, J=1.8 Hz, 1H), 8.71 (d, J=1.9 Hz, 1H), 8.30 (s, 1H), 7.97 (dd, J=8.9, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.1 Hz, 1H), 7.43 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.73-1.62 (m, 2H), 1.57 (d, J=7.4 Hz, 4H).

[0800] MS(ESI, LR) Calculated for C 19 H 18 ClN4O3[M+H] + : 385.1, found: 385.1.

[0801] Example 262. 3-chloro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide

[0802] Example 286. [7-[6-(azetidine-1-carbonyl)-5-chloro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0803] For Examples 262 and 286, compounds were obtained in the same synthetic method as in Step 1-2 in Example 1 using the corresponding compounds and compound 258. The structural and spectral data are shown in Table 11 below.

[0804] Table 11 Example Structure 1H NMR MS 262 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.06 (d, J=1.8 Hz, 1H), 8.72 (d, J=5.0 Hz, 1H), 8.67 (d, J=1.8 Hz, 1H), 8.30 (s, 1H), 7.97 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.42 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.83 (d, J=4.7 Hz, 3H), 1.65 (d, J=5.3 Hz, 2H), 1.57 (d, J=5.1 Hz, 4H). MS(ESI, LR) Calculated for C20H21ClN5O2 [M+H]+: 398.1, found: 398.1. 286 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.08 (d, J=1.8 Hz, 1H), 8.71 (d, J=1.8 Hz, 1H), 8.31 (s, 1H), 7.97 (dd, J=8.9, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.46-7.40 (m, 1H), 4.12 (dt, J=22.1, 7.8 Hz, 4H), 3.63 (t, J=5.4 Hz, 4H), 2.34 (p, J=7.7 Hz, 2H), 1.66 (d, J=5.8 Hz, 2H), 1.58 (d, J=7.8 Hz, 4H). MS(ESI, LR) Calculated for C22H23ClN5O2 [M+H]+: 424.1, found: 424.1.

[0805] MS(ESI, LR) Calculated for C 22 H 23 ClN5O2[M+H] + : 424.1, found: 424.1.

[0806] Example 90.N-(2-cyanoethyl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)furan-2-carboxamide

[0807] <Scheme 10>

[0808]

[0809] Compound 90-1 was prepared by the same synthetic method as used in Example 39C, using compound 1-2 and methyl (5-methoxycarbonyl-2-furyl)boronic acid, and then obtained target compound 90 by the same synthetic method as in both steps 1-2 in Example 1, using 3-aminopropannitrile.

[0810] 1 H NMR (400 MHz, DMSO-d6) δ(m.d.): 9.11 (t,J=5.9 Hz, 1H), 8.42 (s, 1H), 8.05-7.91 (m, 3H), 7.64 (dd,J=8.8, 7.3 Hz, 17,J=3.6), (d,J=5.6). Hz, 1H), 3.64 (t,J=5.4 Hz, 4H), 3.56 (sq.,J=6.3 Hz, 2H), 2.83 (t,J=6.5 Hz, 2H), 1.66 (d,J=4.9 Hz, 2H), 1.58 (d,J=4.0Hz, 4H).

[0811] MS(ESI, LR) Calculated for C 21 H 22N5O3[M+H] + : 392.2, found: 392.1.

[0812] Example 230. (3-hydroxyiminoazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone

[0813]

[0814] After obtaining the intermediate compound in the same synthetic method as in Step 1-2 in Example 1, using compound 39-1 and azetidin-3-one, the target compound 230 was obtained in the same synthetic method as in Step 236-2 in Example 236.

[0815] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 11.07 (d,J=12.6 Hz, 1H), 9.22 (d,J=2.2 Hz, 1H), 9.00 (d,J=2.1 Hz, 1H), 8.68 (s, 1H), 8.27 (d,J=6.5 Hz, 1H), 7.95 (d,J=8.9 Hz, 1H), 7.56 (dd,J=8.9, 7.0 Hz, 1H), 7.37 (d,J=7.0 Hz, 1H), 5.13 (s, 2H), 4.79 (d,J=17.8 Hz, 2H), 3.63 (s, 4H), 1.65 (d,J=6.1 Hz, 2H), 1.57 (s, 4H).

[0816] MS(ESI, LR) Calculated for C 22 H 23 N6O3[M+H] + : 419.2, found: 419.1.

[0817] Example 91. 3-methoxy-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide

[0818] Example 93. 1-Methyl-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide

[0819] Example 94. N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropanecarboxamide

[0820] Example 95.N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide

[0821] Example 96. N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide

[0822] For Examples 91, 93, 94, 95, and 96, compounds were obtained in the same synthetic method as in Step 1-2 in Example 1, using the corresponding compounds and compound 7. The structural and spectral data are shown in Table 12 below.

[0823] Table 12 Example Structure 1H NMR MS 91 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.14 (s, 1H), 8.23 ​​(s, 1H), 8.18 (t, J=2.0 Hz, 1H), 7.88 (dd, J=8.9, 1.4 Hz, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.57-7.45 (m, 3H), 7.12 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (dq, J=5.6, 3.0 Hz, 6H), 3.25 (s, 3H), 2.58 (t, J=6.1 Hz, 2H), 1.65 (d, J=5.6 Hz, 2H), 1.57 (d, J=7.8 Hz, 4H). MS(ESI, LR) Calculated for C23H27N4O3 [M+H]+: 407.2, found: 407.2. 93 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 10.24 (s, 1H), 8.23 ​​(s, 1H), 8.18 (s, 1H), 7.88 (d, J=8.7 Hz, 1H), 7.75 (d, J=8.7 Hz, 1H), 7.75 (d, 8.0 Hz), H (dq, J=15.8, 7.9 Hz, 3H), 7.11 (d, J=7.0 Hz, 1H), 3.62 (s, 4H), 2.98 (s, 2H), 2.78 (s, 2H), 2.03 (s, 3H), 1.66 (s, 2H), 1.25 (s, 2H). MS(ESI, LR) Calculated for C26H32N5O2 [M+H]+: 446.3, found: 446.2. 94 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 10.39 (s, 1H), 8.23 ​​(s, 1H), 8.16 (d, J=2.0 Hz, 1H), 7.88 (dd, J=8.9, 1.4 Hz, 1H), J, 7.8 Hz (7.4 Hz). 1H), 7.57-7.44 (m, 3H), 7.12 (dd, J=7.0, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.85-1.78 (m, 1H), 1.65 (d, J=7.7 Hz, 2H), 0.82 (d, J=5.1 Hz, 4H). MS(ESI, LR) Calculated for C23H25N4O2 [M+H]+: 389.2, found: 389.2. 95 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.64 (s, 1H), 9.14 (d, J=2.3 Hz, 1H), 8.78 (dd, J=4.8, 1.7 Hz, 1H), 8.39-8.28 (m, 2H), 8.25 (s, 1H), 7.92 (dd, J=17.9, 8.5, 1.7 Hz, 2H), 7.66 (d, J=7.8 Hz, 1H), 7.63-7.48 (m, 3H), 7.17 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.57 (d, J=4.8 Hz, 4H). MS(ESI, LR) Calculated for C25H24N5O2 [M+H]+: 426.2, found: 426.1. 96 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.99 (s, 1H), 8.23 ​​(s, 1H), 8.18 (d, J=2.0 Hz, 1H), 7.88 (dd, J=9.0, 1.4 Hz, 1H), 7.75 (d, J=8.1 Hz, 1H), 7.56-7.42 (m, 3H), 7.11 (dd, J=7.0, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.79 (dd, J=22.7, 12.6 Hz, 4H), 1.65 (d, J=7.6 Hz, 2H), 1.57 (s, 4H), 1.42 (q.v., J=12.0 Hz, 2H), 1.25 (dkv., J=24.3, 12.0 Hz, 4H). MS(ESI, LR) Calculated for C26H31N4O2 [M+H]+: 431.2, found: 431.2.

[0824] Example 92. 1-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)urea

[0825] <Diagram 11>

[0826]

[0827] Sodium cyanate (28.4 mg, 0.44 mmol) was dissolved in warm water (3 mL). Compound 7 (70 mg, 0.22 mmol) dissolved in acetic acid (0.5 mL) and water (1.5 mL) was added to the reaction solution, and the mixture was stirred at 50°C for 12 hours. After completion of the reaction, the temperature was lowered using ice water, and the precipitated solid was filtered. The target compound 92 (35.6 mg, 45%) was obtained by recrystallization using boiling water.

[0828] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.74 (s, 1H), 8.22 (s, 1H), 7.95 (d, J=2.1 Hz, 1H), 7.86 (dd, J=8.9, 1.3 Hz, 1H), 7.60-7.54 (m, 1H), 7.50 (dd,J=8.9, 7.0 Hz, 1H), 7.42-7.37 (m, 2H), 7.11 (dd,J=7.0, 1.4 Hz, 1H), 5.91 (s, 2H), 3.62 (t,J=5.3 Hz, 4H), 1.65 (d,J=7.7 Hz, 2H), 1.57 (s, 4H).

[0829] MS(ESI, LR) Calculated for C 20 H 22 N5O2[M+H] + : 364.2, found: 364.2.

[0830] Example 97.N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)acetamide

[0831] Example 98. 3-methoxy-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide

[0832] Example 99. 1-Methyl-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide

[0833] Example 100. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropanecarboxamide

[0834] Example 101.N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide

[0835] Example 102. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide

[0836] Example 274. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide

[0837] For Examples 97, 98, 99, 100, 101, 102 and 274, compounds were obtained in the same synthetic method as in Step 1-2 in Example 1, using the corresponding compounds and compound 14. The structural and spectral data are shown in Table 13 below.

[0838] Table 13 Example Structure 1H NMR MS 97 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.19 (s, 1H), 8.23 ​​(s, 1H), 7.94-7.87 (m, 2H), 7.84 (dd, J=8.9, 1.4 Hz, 1H), 7.75 (d, J=8.6 Hz, 2H), 7.49 (dd, J=8.9, 7.1 Hz, 1H), 7.14 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 2.10 (s, 3H), 1.65 (d, J=6.0 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C21H23N4O2 [M+H]+: 363.2, found: 363.2. 98 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.20 (s, 1H), 8.23 ​​(s, 1H), 7.93-7.88 (m, 2H), 7.84 (dd, J=8.9, 1.4 Hz, 1H), 7.77 (d, J=8.7 Hz, 2H), 7.49 (dd, J=8.9, 7.1 Hz, 1H), 7.14 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (dt, J=11.6, 5.8 Hz, 6H), 3.26 (s, 3H), 2.60 (t, J=6.2 Hz, 2H), 1.65 (d, J=5.9 Hz, 2H), 1.56 (s, 4H). MS(ESI, LR) Calculated for C23H27N4O3 [M+H]+: 407.2, found: 407.2. 99 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.46 (s, 1H), 8.23 ​​(s, 1H), 7.92 (d, J=8.5 Hz, 2H), 7.82 (dd, J=15.7, 8.7 Hz, 3H), 7.49 (dd, J=8.9, 7.1 Hz, 1H), 7.14 (d, J=7.0 Hz, 1H), 3.62 (t, J=5.5 Hz, 4H), 2.73 (s, 3H), 2.09-1.91 (m, 4H), 1.64 (t, J=5.5 Hz, 2H), 1.56 (sq., J=5.4 Hz, 4H), 1.31-1.16 (m, 3H). MS(ESI, LR) Calculated for C26H32N5O2 [M+H]+: 446.3, found: 446.4. 100 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.45 (s, 1H), 8.23 ​​(s, 1H), 7.91 (d, J=8.6 Hz, 2H), 7.84 (dd, J=8.9, 1.3 Hz, 1H), 7.76 (d, J=8.7 Hz, 2H), 7.49 (dd, J=8.9, 7.1 Hz, 1H), 7.15 (dd, J=7.0, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.87-1.78 (m, 1H), 1.65 (d, J=6.9 Hz, 2H), 1.57 (d, J=7.6 Hz, 4H), 0.87-0.83 (m, 4H). MS(ESI, LR) Calculated for C23H25N4O2 [M+H]+: 389.2, found: 389.2. 101 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.69 (s, 1H), 9.16 (d, J=2.2 Hz, 1H), 8.80 (dd, J=4.8, 1.7 Hz, 1H), 8.37-8.32 (m, 1H), 8.25 (s, 1H), 8.06-7.92 (m, 4H), 7.89-7.84 (m, 1H), 7.61 (dd, J=8.0, 4.8 Hz, 1H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.20 (d, J=7.0 Hz, 1H), 3.64 (d, J=5.9 Hz, 4H), 1.66 (s, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C25H24N5O2 [M+H]+: 426.2, found: 426.1. 102 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.05 (s, 1H), 8.23 ​​(s, 1H), 7.90 (d, J=8.7 Hz, 2H), 7.84 (dd, J=9.0, 1.3 Hz, 1H), 7.78 (d, J=8.7 Hz, 2H), 7.49 (dd, J=8.9, 7.1 Hz, 1H), 7.14 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.81 (dd, J=23.4, 12.8 Hz, 4H), 1.66 (s, 2H), 1.57 (s, 4H), 1.44 (sq., J=11.9 Hz, 2H), 1.27 (dq., J=23.5, 12.0 Hz, 4H). MS(ESI, LR) Calculated for C26H31N4O2 [M+H]+: 431.2, found: 431.2. 274 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.49 (s, 1H), 8.56 (d, J=2.4 Hz, 1H), 8.52-8.43 (m, 1H), 8.23 ​​(s, 1H), 7.93 (d, J=8.5 Hz, 2H), 7.85 (d, J=8.9 Hz, 1H), 7.80-7.72 (m, 3H), 7.49 (dd, J=8.9, 7.0 Hz, 1H), 7.39 (dd, J=7.9, 4.8 Hz, 1H), 7.15 (d, J=7.0 Hz, 1H), 3.78 (s, 2H), 3.62 (t, J=5.3 Hz, 4H), 1.65 (d, J=5.6 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C26H26N5O2 [M+H]+: 440.2, found: 440.1.

[0839] Example 196. 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0840] Example 197. 3-methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)propenamide

[0841] Example 198. 2-oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)piperidin-4-carboxamide

[0842] Example 326.N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide

[0843] Example 327.N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyridin-3-yl)acetamide

[0844] Example 333. 1,2-Dimethyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1H-imidazol-5-carboxamide

[0845] Example 334.N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)pyrimidin-5-carboxamide

[0846] Example 335. 5-fluoro-N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide

[0847] Example 388. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetamide

[0848] Example 389. 2-phenyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0849] Example 402. 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0850] Example 403.N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyrimidin-5-yl)acetamide

[0851] Example 406. 2-(4-chlorophenoxy)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0852] For Examples 196, 197, 198, 326, 327, 333, 334, 335, 388, 389, 402, 403 and 406, compounds were obtained in the same synthetic method as in Step 1-2 in Example 1, using the corresponding compounds and compound 9. The structural and spectral data are shown in Table 14 below.

[0853] Table 14 Example Structure 1H NMR MS 196 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.18 (s, 1H), 8.99 (d, J=2.4 Hz, 1H), 8.75 (d, J=2.0 Hz, 1H), 8.70 (t, J=2.2 Hz, 1H), 8.27 (s, 1H), 7.93 (dd, J=8.9, 1.4 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.15 (s, 2H), 2.31 (s, 6H), 1.65 (d, J=5.4 Hz, 2H), 1.57 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C22H27N6O2 [M+H]+: 407.2, found: 407.1. 197 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.40 (s, 1H), 8.89 (d, J=2.4 Hz, 1H), 8.72 (d, J=2.0 Hz, 1H), 8.67 (t, J=2.2 Hz, 1H), 8.27 (s, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (sq, J=6.1 Hz, 6H), 3.26 (s, 3H), 2.63 (t, J=6.1 Hz, 2H), 1.65 (d, J=6.5 Hz, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C22H26N5O3 [M+H]+: 408.2, found: 408.1. 198 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.45 (s, 1H), 8.90 (d, J=2.4 Hz, 1H), 8.73 (d, J=2.0 Hz, 1H), 8.68 (t, J=2.2 Hz, 1H), 8.27 (s, 1H), 7.93 (dd, J=8.9, 1.4 Hz, 1H), 7.58-7.51 (m, 2H), 7.26 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.26-3.13 (m, 2H), 2.98-2.89 (m, 1H), 2.36 (d, J=7.7 Hz, 2H), 1.65 (d, J=5.8 Hz, 2H), 1.57 (s, 4H), 1.25 (s, 2H). MS(ESI, LR) Calculated for C24H27N6O3 [M+H]+: 447.2, found: 447.2. 326 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.86 (s, 1H), 9.17 (d, J=2.2 Hz, 1H), 9.08 (d, J=1.5 Hz, 1H), 8.86-8.77 (m, 3H), 8.36 (dt, J=8.0, 2.0 Hz, 1H), 8.27 (s, 1H), 7.94 (dd, J=9.0, 1.3 Hz, 1H), 7.61 (dd, J=8.0, 4.8 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.30 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (sq., J=5.8 Hz, 2H), 1.61-1.47 (m, 4H). MS(ESI, LR) Calculated for C24H23N6O3 [M+H]+: 427.2, found: 427.1. 327 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.67 (s, 1H), 8.90 (d, J=2.4 Hz, 1H), 8.74 (d, J=2.0 Hz, 1H), 8.67 (t, J=2.2 Hz, 1H), 8.55 (d, J=2.3 Hz, 1H), 8.48 (dd, J=4.8, 1.7 Hz, 1H), 8.25 (s, 1H), 7.92 (dd, J=8.9, 1.4 Hz, 1H), 7.77 (dt, J=8.0, 2.0 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.37 (dd, J=7.8, 4.8 Hz, 1H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 3.80 (s, 2H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (m, 2H), 1.57 (m, 4H). MS(ESI, LR) Calculated for C25H25N6O2 [M+H]+: 441.2, found: 441.1. 333 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 10.32 (s, 1H), 9.01 (d, J=2.4 Hz, 1H), 8.77 (d, J=2.0 Hz, 1H), 8.72 (t, J=2.2 Hz, 1H), 8.72 (t, J=2.2 Hz, 1H), 7.94 (dd, J=8.9, 1.4 Hz, 1H), 7.78 (s, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.28 (dd, J=7.1, 1.4 Hz, 1H), 3.80 (s, 3H), 3.4 Hz, J 4H), 2.37 (s, 3H), 1.66 (m, 2H), 1.58 (m, 4H). MS(ESI, LR) Calculated for C24H26N7O2 [M+H]+: 444.2, found: 444.1. 334 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 11.01 (s, 1H), 9.40 (s, 1H), 9.33 (s, 2H), 9.07 (d, J=2.3 Hz, 1H), 8.84 (dd, J=2.3 Hz, 1H), 8.84 (dd, J=2.7 Hz, 2.8 H), (s, 1H), 7.95 (dd, J=8.9, 1.4 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.31 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 1.4 Hz), (1H), 1.58 (m, 4H). MS(ESI, LR) Calculated for C23H22N7O2 [M+H]+: 428.2, found: 428.1. 335 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 10.90 (s, 1H), 9.12-8.98 (m, 2H), 8.83 (dt, J=9.0, 2.0 Hz, 3H), 8.34-8.20 (m, 2Hz, 9.8, J=9.8), (dd 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.30 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.71-1.59 (m, 2H, 1.60, 4H). MS(ESI, LR) Calculated for C24H22FN6O2 [M+H]+: 445.2, found: 445.1. 388 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 10.75 (s, 1H), 8.90 (d, J=2.4 Hz, 1H), 8.75 (t, J=2.4 Hz, 2H), 8.67 (t, J=2.4 Hz, 2H), 8.67 (t, J=2.3 Hz, 18, 1H), 8.12-7.99 (m, 1H), 7.96-7.84 (m, 2H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 3.97 (s, 2H), 3.5 Hz, J 1.65 (m, 2H), 1.57 (m, 2H), 1.25 (m, 2H). MS(ESI, LR) Calculated for C26H24F3N6O2 [M+H]+: 509.2, found: 509.1. 389 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.62 (s, 1H), 8.90 (d, J=2.4 Hz, 1H), 8.72 (d, J=2.0 Hz, 1H), 8.67 (t, J=2.2 Hz, 1H), 8.26 (s, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.52 (dd, J=8.9, 7.0 Hz, 1H), 7.42-7.16 (m, 5H), 3.73 (s, 2H), 3.62 (t, J=5.4 Hz, 3H), 1.65 (m, 2H), 1.56 (m, 2H), 1.25 (m, 2H). MS(ESI, LR) Calculated for C26H26N5O2 [M+H]+: 440.2, found: 440.1. 402 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.71 (s, 1H), 8.90 (d, J=2.4 Hz, 1H), 8.75 (d, J=2.0 Hz, 1H), 8.67 (t, J=2.2 Hz, 1H), 8.50 (d, J=2.8 Hz, 1H), 8.43 (t, J=1.8 Hz, 1H), 8.26 (s, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.73 (dt, J=10.0, 2.2 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 3.88 (s, 2H), 3.62 (m, 4H), 1.65 (m, 2H), 1.56 (m, 4H). MS(ESI, LR) Calculated for C25H24FN6O2 [M+H]+: 459.2, found: 459.1. 403 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.75 (s, 1H), 9.10 (s, 1H), 8.89 (d, J=2.4 Hz, 1H), 8.78 (s, 2H), 8.75 (d, J=1.9 Hz, 1H), 8.68 (d, J=2.2 Hz, 1H), 8.25 (s, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 3.87 (s, 2H), 3.62 (t, J=5.4 Hz, 5H), 1.65 (m, 2H), 1.56 (m, 4H). MS(ESI, LR) Calculated for C24H24N7O2 [M+H]+: 442.2, found: 442.2. 406 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.56 (s, 1H), 8.96 (d, J=2.4 Hz, 1H), 8.78 (d, J=2.0 Hz, 1H), 8.70 (t, J=2.2 Hz, 1H), 8.26 (s, 1H), 7.93 (dd, J=8.9, 1.4 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.42-7.35 (m, 2H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 7.12-7.02 (m, 2H), 4.81 (s, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.73-1.62 (m, 2H), 1.57 (m, 4H). MS(ESI, LR) Calculated for C26H25ClN5O3 [M+H]+: 490.2, found: 490.1.

[0854] Example 103. 3-methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)propanamide

[0855] <Scheme 12>

[0856]

[0857] Compound 17 (50 mg, 0.16 mmol) was dissolved in N,N-dimethylformamide (5 mL), and triethylamine (64 μL, 0.47 mmol) was added. 3-Methoxypropionyl chloride (28 mg, 0.23 mmol) was added to the reaction solution, and the mixture was stirred at room temperature for 12 hours. After completion of the reaction, the reaction solution was concentrated, diluted with ethyl acetate (20 mL), and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to obtain the target compound 103 (27.2 mg, 43%).

[0858] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 10.75 (s, 1H), 8.89 (d, J=2.4 Hz, 1H), 8.40 (dd, J=8.8, 2.4 Hz, 1H), 8.28-8.25 (m, 1H), 7.89 (dd,J=8.8, 1.3 Hz, 1H), 7.52 (dd,J=8.9, 7.1 Hz, 1H), 7.27 (dd,J=7.1, 1.4 Hz, 1H), 5.75 (s, 1H), 3.64 (dt,J=10.7, 5.7 Hz, 6H), 3.26 (s, 3H), 2.70 (t, J=6.2 Hz, 2H), 1.65 (d,J=5.6 Hz, 2H), 1.57 (s, 4H).

[0859] MS(ESI, LR) Calculated for C 23 H 28 N5O3[M+H] + : 408.2, found: 408.1.

[0860] Example 104. 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide

[0861] <Diagram 13>

[0862]

[0863] HOBt (21 mg, 0.16 mmol) and EDCI⋅HCl (71.6 mg, 0.37 mmol) were dissolved in dichloromethane (10 mL), triethylamine (64.7 μL, 0.47 mmol) was added, and stirred for 1 hour. Compound 17 (0.1 g, 0.31 mmol) was added to the reaction solution, and stirred for 3 hours. After completion of the reaction, the reaction solution was diluted with dichloromethane (20 mL) and washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated using column chromatography to give the target compound 104 (36.3 mg, 29%). [HOBt (Hydroxybenzotriazole), EDCI (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide)]

[0864] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 10.17 (s, 1H), 8.88 (d, J=2.4 Hz, 1H), 8.43 (dd, J=8.7, 2.4 Hz, 1H), 8.30-8.22 (m, 2H), 7.89 (dd, J=8.9, 1.4 Hz, 1H), 7.52 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 3.20 (s, 2H), 2.33 (s, 6H), 1.65 (d, J=7.6 Hz, 2H), 1.57 (sq., J=5.8 Hz, 4H).

[0865] MS(ESI, LR) Calculated for C 22 H 27 N6O2[M+H] + : 407.2, found: 407.1.

[0866] Example 105. 2-oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)piperidin-4-carboxamide

[0867] <Diagram 14>

[0868]

[0869] HOBt (42 mg, 0.31 mmol), EDCI⋅HCl (58 mg, 0.37 mmol), and 4-dimethylaminopyridine (19 mg, 0.15 mmol) were dissolved in dichloromethane (7 mL), triethylamine (86 μL, 0.62 mmol) was added, and stirred for 1 hour. Compound 17 (0.1 mg, 0.31 mmol) was added to the reaction solution, which was stirred for 3 hours. After completion of the reaction, the reaction solution was diluted with dichloromethane (20 mL) and washed with water. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to obtain the target compound 105 (29.8 mg, 22%).

[0870] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 10.87 (s, 1H), 8.90 (d,J=2.4 Hz, 1H), 8.41 (dd,J=8.8, 2.4 Hz, 1H), 8.26 (d,J=7.7 Hz, 2H), 7.91-7.86 (m, 1H), 7.52 (t,J=7.9 Hz, 2H), 7.27 (d,J=7.0 Hz, 1H), 3.62 (t,J=5.5 Hz, 4H), 3.24-3.00 (m, 4H), 2.35 (d, J=7.7 Hz, 2H), 2.05-1.96 (m, 1H), 1.65 (s, 2H), 1.57 (s, 4H).

[0871] MS(ESI, LR) Calculated for C24 H 27 N6O3[M+H] + : 447.2, found: 447.1

[0872] Example 106.N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide

[0873]

[0874] The target compound 106 was obtained in the same synthetic method as in Example 105 using compound 17 and 2-(3-pyridyl)acetic acid.

[0875] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 11.10 (s, 1H), 8.91 (dd, J=2.4, 0.9 Hz, 1H), 8.56 (d, J=2.3 Hz, 1H), 8.48 (dd, J=4.8, 1.7 Hz, 1H), 8.40 (dd, J=8.7, 2.4 Hz, 1H), 8.26 (s, 1H), 8.21 (d, J=8.7 Hz, 1H), 7.89 (dd, J=8.8, 1.4 Hz, 1H), 7.78 (dt, J=7.8, 2.1 Hz, 1H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.42-7.34 (m, 1H), 7.27 (dd,J=7.1, 1.3 Hz, 1H), 3.85 (s, 2H), 3.62 (t,J=5.4 Hz, 4H), 1.65 (d,J=5.6 Hz, 2H), 1.56 (d,J=7.1 Hz, 4H).

[0876] MS(ESI, LR) Calculated for C 25 H 25 N6O2[M+H] + : 441.2, found: 441.1

[0877] Example 407.N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-2-pyrimidin-5-yl-acetamide

[0878] Example 408.N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-2-[6-(trifluoromethyl)-3-pyridyl]acetamide

[0879] Example 409. 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide

[0880] Example 410. 2-(4-chlorophenoxy)-N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]acetamide

[0881] For Examples 407, 408, 409, and 410, compounds were prepared by the same synthetic method as in Step 1-2 of Example 1, using compound 17 and the corresponding compounds. The structural and spectral data are shown in Table 15 below.

[0882] Table 15 Example Structure 1H NMR MS 407 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.15 (s, 1H), 9.11 (s, 1H), 8.95-8.90 (m, 1H), 8.79 (s, 2H), 8.41 (dd, J=8.8, 2.4 Hz, 1H), 8.27 (s, 1H), 8.21 (d, J=8.8 Hz, 1H), 7.89 (dd, J=8.9, 1.3 Hz, 1H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.28 (dd, J=7.1, 1.3 Hz, 1H), 3.93 (s, 2H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=5.8 Hz, 2H), 1.57 (s, 5H). MS(ESI, LR) Calculated for C24H24N7O2 [M+H]+: 442.2, found: 442.1. 408 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.17 (s, 1H), 8.96-8.87 (m, 1H), 8.75 (d, J=2.1 Hz, 1H), 8.41 (dd, J=8.8, 2.4 Hz, 1H), 8.27 (s, 1H), 8.21 (d, J=8.8 Hz, 1H), 8.08 (dd, J=8.5, 2.1 Hz, 1H), 7.94-7.84 (m, 2H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.28 (dd, J=7.0, 1.3 Hz, 1H), 4.02 (s, 2H), 3.62 (d, J=5.3 Hz, 4H), 1.65 (d, J=5.9 Hz, 2H), 1.56 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C26H24F3N6O2[M+H]+: 509.2, found: 509.1. 409 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.11 (s, 1H), 8.92 (d, J=2.4 Hz, 1H), 8.50 (d, J=2.8 Hz, 1H), 8.44 (t, J=1.9 Hz, 1H), 8.40 (dd, J=8.8, 2.4 Hz, 1H), 8.26 (s, 1H), 8.21 (d, J=8.7 Hz, 1H), 7.89 (dd, J=8.9, 1.4 Hz, 1H), 7.73 (dt, J=9.8, 2.3 Hz, 1H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 3.93 (s, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.64 (d, J=7.1 Hz, 2H), 1.57 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C25H24FN6O2[M+H]+: 459.2, found: 459.2. 410 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.88 (s, 1H), 8.97-8.88 (m, 1H), 8.43 (dd, J=8.8, 2.4 Hz, 1H), 8.27 (s, 1H), 8.21 (d, J=8.7 Hz, 1H), 7.89 (dd, J=8.9, 1.3 Hz, 1H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.43-7.32 (m, 2H), 7.28 (dd, J=7.1, 1.4 Hz, 1H), 7.08-6.97 (m, 2H), 4.88 (s, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.3 Hz, 2H), 1.57 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C26H25ClN5O3[M+H]+: 490.2, found: 490.1.

[0883] Example 278. N-(2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide

[0884] <Scheme 15>

[0885]

[0886] Step 278-1: The target compound 278-1 was obtained in the same synthetic method as in Step 1-2 in Example 1 using 4-bromo-2,6-difluoroaniline and 2-(3-pyridyl)acetic acid.

[0887] Step 278-2: The target compound 278-2 was obtained in the same synthetic method as in Step 351-1 in Example 351 using compound 278-1.

[0888] Step 278-3: The target compound 278 was obtained in the same synthetic method as in Step 159-3 of Example 159 using compound 278-2.

[0889] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 10.21 (s, 1H), 8.56 (d, J=2.3 Hz, 1H), 8.49 (dd, J=4.8, 1.7 Hz, 1H), 8.27 (s, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.84 (d, J=8.9 Hz, 2H), 7.82-7.72 (m, 1H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.40 (dd, J=7.9, 4.8 Hz, 1H), 7.32 (dd, J=7.1, 1.3 Hz, 1H), 3.82 (s, 2H), 3.62 (t,J=5.4 Hz, 4H), 1.65 (d,J=5.6 Hz, 2H), 1.56 (d,J=6.9 Hz, 4H).

[0890] MS(ESI, LR) Calculated for C 26 H 24 F2N5O2[M+H] + : 476.2, found: 476.1.

[0891] Example 107. (7-(6-((3-methoxypropyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0892] <Diagram 16>

[0893]

[0894] Potassium carbonate (0.106 g, 0.77 mmol) was added to a solution of 3-methoxypropylamine (47 μL, 0.46 mmol) in N,N-dimethylformamide (6 mL), and stirred for 10 minutes. Compound 19 (0.1 g, 0.31 mmol) was added to the reaction solution, and the mixture was stirred at 100 °C for 12 hours. After completion of the reaction, the reaction solution was concentrated, diluted with dichloromethane (20 mL), and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to obtain the target compound 107 (0.059 g, 49%).

[0895] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.55 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.02 (dd, J=8.9, 2.5 Hz, 1H), 7.78 (dd, J=8.9, 1.4 Hz, 1H), 7.46 (dd, J=8.9, 7.1 Hz, 1H), 7.11 (dd, J=7.2, 1.4 Hz, 1H), 6.59 (d, J=8.9 Hz, 1H), 3.61 (t, J=5.4 Hz, 4H), 3.42 (t, J=6.3 Hz, 2H), 3.38 (d, J=6.7 Hz, 2H), 3.26 (s, 3H), 1.80 (p, J=6.6 Hz, 2H), 1.65 (d, J=6.0 Hz, 2H), 1.56 (d, J=7.1 Hz, 4H).

[0896] MS(ESI, LR) Calculated for C 22 H 28 N5O2[M+H] + : 394.2, found: 394.2.

[0897] Example 108. (7-(6-morpholinopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0898] Example 109. (7-(6-(isopropylamino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0899] Example 110. piperidin-1-yl(7-(6-(piperidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[0900] Example 111. (7-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0901] Example 206. (7-(6-(azetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0902] Example 208. (7-(6-(3-fluoroazetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0903] Example 209. (7-(6-(3,3-difluoroazetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0904] Example 210. (7-(6-(3-hydroxyazetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0905] Example 215. (7-(6-(2-azabicyclo[2,2,1]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0906] Example 216. (7-(6-(2-azabicyclo[2,2,2]octane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0907] Example 217. -(6-(7-azabicyclo[2,2,1]heptane-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0908] Example 218. (7-(6-(3-(dimethylamino)azetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0909] Example 219. methyl 1-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridine-7-yl)pyridin-2-yl)azetidine-3-carboxylate

[0910] Example 220. (7-(6-(2-azaspiro[3,3]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0911] Example 221. (7-(6-(3-(hydroxymethyl)azetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0912] Example 222. (7-(6-(7-azaspiro[3,5]nonan-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0913] Example 223. (7-(6-(6-azaspiro[3,4]octan-6-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0914] Example 332. piperidin-1-yl(7-(6-(((2-(pyridin-3-yl)ethyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[0915] Example 344. (7-(6-(4-amino-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0916] For Examples 108, 109, 110, 111, 206, 208, 209, 210, 215, 216, 217, 218, 219, 220, 221, 222, 223, 332 and 344, compounds were obtained in the same synthetic method as in Example 107 using the corresponding compounds and compound 19. The structural and spectral data are shown in Table 16 below.

[0917] Table 16 Example Structure 1H NMR MS 108 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.70 (d, J=2.5 Hz, 1H), 8.22 (d, J=9.5 Hz, 2H), 7.81 (dd, J=8.8, 1.3 Hz, 1H), 7.48 (dd, J=8.9, 7.1 Hz, 1H), 7.18 (dd, J=7.1, 1.3 Hz, 1H), 6.99 (d, J=9.0 Hz, 1H), 3.74 (t, J=4.8 Hz, 4H), 3.60 (dt, J=9.9, 5.0 Hz, 8H), 1.65 (d, J=5.6 Hz, 2H), 1.57 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C22H26N5O2 [M+H]+: 392.2, found: 392.2. 109 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.55 (d, J=2.5 Hz, 1H), 8.22 (s, 1H), 8.00 (dd, J=8.9, 2.5 Hz, 1H), 7.77 (dd, J=8.8, 1.4 Hz, 1H), 7.46 (dd, J=8.9, 7.1 Hz, 1H), 7.11 (dd, J=7.1, 1.4 Hz, 1H), 6.89 (d, J=7.6 Hz, 1H), 6.57 (d, J=8.9 Hz, 1H), 4.11 (h, J=6.6 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.7 Hz, 2H), 1.62-1.53 ​​(m, 4H), 1.19 (d, J=6.5 Hz, 6H). MS(ESI, LR) Calculated for C21H26N5O [M+H]+: 364.2, found: 364.2. 110 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.67 (d, J=2.5 Hz, 1H), 8.23 ​​(s, 1H), 8.16 (dd, J=9.0, 2.6 Hz, 1H), 7.80 (dd, J=8.8, 1.4 Hz, 1H), 7.47 (dd, J=8.8, 7.1 Hz, 1H), 7.16 (dd, J=7.2, 1.4 Hz, 1H), 6.96 (d, J=9.1 Hz, 1H), 3.64 (dt, J=13.9, 5.4 Hz, 8H), 1.66 (dt, J=9.2, 5.6 Hz, 4H), 1.58 (p, J=5.8 Hz, 8H). MS(ESI, LR) Calculated for C23H28N5O [M+H]+: 390.2, found: 390.2. 111 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.68 (d, J=2.5 Hz, 1H), 8.23 ​​(s, 1H), 8.19 (dd, J=9.0, 2.5 Hz, 1H), 7.81 (dd, J=8.9, 1.3 Hz, 1H), 7.47 (dd, J=8.8, 7.1 Hz, 1H), 7.17 (dd, J=7.1, 1.4 Hz, 1H), 6.98 (d, J=9.1 Hz, 1H), 3.63 (dd, J=6.4, 3.2 Hz, 8H), 2.42 (t, J=5.1 Hz, 4H), 2.24 (s, 3H), 1.65 (d, J=8.5 Hz, 2H), 1.56 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C23H29N6O [M+H]+: 405.2, found: 405.2. 206 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.61 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.15 (dd, J=8.7, 2.4 Hz, 1H), 7.80 (dd, J=8.8, 1.4 Hz, 1H), 7.47 (dd, J=8.9, 7.1 Hz, 1H), 7.13 (dd, J=7.1, 1.4 Hz, 1H), 6.48 (d, J=8.8 Hz, 1H), 4.05 (t, J=7.4 Hz, 4H), 3.61 (t, J=5.4 Hz, 4H), 2.38 (p, J=7.4 Hz, 2H), 1.65 (sq., J=5.8 Hz, 2H), 1.57 (sq., J=5.6 Hz, 4H). MS(ESI, LR) Calculated for C21H24N5O [M+H]+: 362.2, found: 362.1. 208 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.64 (d, J=2.3 Hz, 1H), 8.23 ​​(s, 1H), 8.19 (dd, J=8.7, 2.4 Hz, 1H), 7.82 (dd, J=8.9, 1.4 Hz, 1H), 7.48 (dd, J=8.8, 7.1 Hz, 1H), 7.16 (dd, J=7.1, 1.4 Hz, 1H), 6.61 (d, J=8.7 Hz, 1H), 5.64-5.47 (m, 1H), 4.45-4.32 (m, 2H), 4.17-4.06 (m, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.61 (dd, J=34.5, 6.4 Hz, 6H). MS(ESI, LR) Calculated for C21H23FN5O [M+H]+: 380.2, found: 380.1. 209 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.69 (d, J=2.3 Hz, 1H), 8.27-8.21 (m, 2H), 7.84 (dd, J=8.8, 1.4 Hz, 1H), 7.49 (dd, J=8.9, 7.1 Hz, 1H), 7.18 (dd, J=7.0, 1.4 Hz, 1H), 6.74 (d, J=8.7 Hz, 1H), 4.50 (t, J=12.5 Hz, 4H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.0 Hz, 2H), 1.56 (d, J=7.7 Hz, 4H). MS(ESI, LR) Calculated for C21H22F2N5O [M+H]+: 398.2, found: 398.1. 210 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.61 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.15 (dd, J=8.7, 2.4 Hz, 1H), 7.80 (dd, J=8.9, 1.4 Hz, 1H), 7.47 (dd, J=8.9, 7.1 Hz, 1H), 7.14 (dd, J=7.1, 1.4 Hz, 1H), 6.52 (d, J=8.7 Hz, 1H), 5.73 (d, J=6.4 Hz, 1H), 4.63 (q, J=5.4 Hz, 1H), 4.26 (dd, J=8.9, 6.6 Hz, 2H), 3.78 (dd, J=9.0, 4.6 Hz, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.4 Hz, 2H), 1.56 (d, J=4.6 Hz, 4H). MS(ESI, LR) Calculated for C21H24N5O2 [M+H]+: 378.2, found: 378.1. 215 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.61 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.11 (dd, J=8.9, 2.5 Hz, 1H), 7.78 (dd, J=8.9, 1.4 Hz, 1H), 7.46 (dd, J=8.8, 7.1 Hz, 1H), 7.12 (dd, J=7.1, 1.4 Hz, 1H), 4.60 (s, 1H), 3.62 (t, J=5.4 Hz, 4H), 3.45 (d, J=9.5 Hz, 1H), 3.10 (s, 1H), 2.66 (s, 1H), 1.76-1.50 (m, 11H), 1.39 (t, J=8.5 Hz, 1H). MS(ESI, LR) Calculated for C24H28N5O [M+H]+: 402.2, found: 402.1. 216 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.62 (d, J=2.5 Hz, 1H), 8.22 (s, 1H), 8.15 (dd, J=9.0, 2.5 Hz, 1H), 7.78 (dd, J=8.9, 1.3 Hz, 1H), 7.47 (dd, J=8.9, 7.1 Hz, 1H), 7.13 (dd, J=7.0, 1.4 Hz, 1H), 6.62 (d, J=9.0 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 3.43 (s, 2H), 2.03 (s, 1H), 1.88-1.52 (m, 16H). MS(ESI, LR) Calculated for C25H30N5O [M+H]+: 416.2, found: 416.1. 217 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.66 (d, J=2.4 Hz, 1H), 8.23 ​​(s, 1H), 8.17 (dd, J=8.8, 2.5 Hz, 1H), 7.81 (dd, J=8.8, 1.4 Hz, 1H), 7.48 (dd, J=8.9, 7.0 Hz, 1H), 7.17 (dd, J=7.1, 1.3 Hz, 1H), 7.01 (d, J=8.8 Hz, 1H), 4.64-4.56 (m, 2H), 3.62 (t, J=5.5 Hz, 4H), 1.76-1.46 (m, 14H). MS(ESI, LR) Calculated for C24H28N5O [M+H]+: 402.2, found: 402.1. 218 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.62 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.16 (dd, J=8.8, 2.4 Hz, 1H), 7.80 (dd, J=8.9, 1.4 Hz, 1H), 7.47 (dd, J=8.8, 7.1 Hz, 1H), 7.14 (dd, J=7.1, 1.4 Hz, 1H), 6.52 (d, J=8.7 Hz, 1H), 4.08 (dd, J=8.6, 6.9 Hz, 2H), 3.82 (dd, J=8.7, 5.2 Hz, 2H), 3.61 (t, J=5.4 Hz, 4H), 3.27-3.20 (m, 1H), 2.14 (s, 6H), 1.65 (d, J=6.0 Hz, 2H), 1.57 (t, J=6.7 Hz, 4H). MS(ESI, LR) Calculated for C23H29N6O [M+H]+: 405.2, found: 405.1. 219 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.63 (d, J=2.3 Hz, 1H), 8.22 (s, 1H), 8.18 (dd, J=8.7, 2.4 Hz, 1H), 7.81 (dd, J=8.9, 1.4 Hz, 1H), 7.48 (dd, J=8.9, 7.1 Hz, 1H), 7.15 (dd, J=7.1, 1.3 Hz, 1H), 6.58 (d, J=8.8 Hz, 1H), 4.26 (t, J=8.6 Hz, 2H), 4.12 (dd, J=8.3, 5.8 Hz, 2H), 3.71 (s, 4H), 3.62 (t, J=5.5 Hz, 4H), 1.65 (d, J=8.2 Hz, 2H), 1.56 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C23H26N5O3 [M+H]+: 420.2, found: 420.1. 220 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.61 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.14 (dd, J=8.8, 2.4 Hz, 1H), 7.80 (dd, J=8.9, 1.4 Hz, 1H), 7.47 (dd, J=8.9, 7.1 Hz, 1H), 7.13 (dd, J=7.1, 1.4 Hz, 1H), 6.49 (d, J=8.8 Hz, 1H), 4.02 (s, 4H), 3.62 (t, J=5.4 Hz, 4H), 2.22 (t, J=7.6 Hz, 4H), 1.84 (p, J=7.5 Hz, 2H), 1.69-1.61 (m, 2H), 1.56 (s, 4H). MS(ESI, LR) Calculated for C24H28N5O [M+H]+: 420.2, found: 420.1. 221 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.61 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.14 (dd, J=8.7, 2.4 Hz, 1H), 7.80 (dd, J=8.9, 1.4 Hz, 1H), 7.47 (dd, J=8.8, 7.1 Hz, 1H), 7.13 (dd, J=7.1, 1.4 Hz, 1H), 6.49 (d, J=8.8 Hz, 1H), 4.81 (t, J=5.3 Hz, 1H), 4.06 (t, J=8.2 Hz, 2H), 3.79 (dd, J=8.3, 5.4 Hz, 2H), 3.61 (t, J=5.8 Hz, 6H), 2.85 (ddd, J=13.7, 7.5, 5.3 Hz, 1H), 1.61 (dd, J=35.4, 6.3 Hz, 6H). MS(ESI, LR) Calculated for C22H26N5O2 [M+H]+: 392.2, found: 392.1. 222 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.66 (d, J=2.5 Hz, 1H), 8.22 (s, 1H), 8.15 (dd, J=9.0, 2.5 Hz, 1H), 7.79 (dd, J=8.8, 1.4 Hz, 1H), 7.47 (dd, J=8.8, 7.1 Hz, 1H), 7.15 (dd, J=7.1, 1.3 Hz, 1H), 6.97 (d, J=9.1 Hz, 1H), 3.66-3.54 (m, 8H), 1.96-1.76 (m, 6H), 1.69-1.51 (m, 10H). MS(ESI, LR) Calculated for C26H32N5O [M+H]+: 430.2, found: 430.1. 223 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.64 (d, J=2.4 Hz, 1H), 8.22 (s, 1H), 8.14 (dd, J=8.9, 2.5 Hz, 1H), 7.78 (dd, J=8.9, 1.4 Hz, 1H), 7.46 (dd, J=8.8, 7.1 Hz, 1H), 7.13 (dd, J=7.2, 1.4 Hz, 1H), 6.57 (d, J=8.9 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 3.47 (d, J=6.5 Hz, 4H), 2.09-1.87 (m, 8H), 1.65 (d, J=5.6 Hz, 2H), 1.56 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C25H30N5O [M+H]+: 416.2, found: 416.1. 332 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.59 (d, J=2.4 Hz, 1H), 8.50 (d, J=2.3 Hz, 1H), 8.43 (dd, J=4.8, 1.7 Hz, 1H), 8.22 (s, 1H), 8.03 (dd, J=8.8, 2.5 Hz, 1H), 7.78 (dd, J=8.9, 1.4 Hz, 1H), 7.70 (dt, J=7.9, 2.0 Hz, 1H), 7.46 (dd, J=8.9, 7.1 Hz, 1H), 7.34 (dd, J=7.7, 4.8 Hz, 1H), 7.19-7.05 (m, 2H), 6.63 (d, J=8.8 Hz, 1H), 3.71-3.54 (m, 6H), 2.92 (t, J=7.1 Hz, 2H), 1.65 (q, J=5.8 Hz, 2H), 1.57 (q, J=5.8 Hz, 4H). MS(ESI, LR) Calculated for C25H27N6O [M+H]+: 427.2, found: 427.2. 344 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.93 (d, J=2.3 Hz, 1H), 8.50 (dd, J=8.7, 2.4 Hz, 1H), 8.27 (s, 1H), 7.98-7.88 (m, 3H), 7.56-7.51 (m, 1H), 7.44 (s, 1H), 7.34-7.29 (m, 1H), 4.39 (s, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (s, 2H), 1.58 (s, 4H). MS(ESI, LR) Calculated for C21H22N7O [M+H]+: 388.2, found: 388.1.

[0918] Example 287.N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide

[0919] <Diagram 17>

[0920]

[0921] Compound 19 (36.5 mg, 0.11 mmol), pyridine-3-carboxamide (20.6 mg, 0.17 mmol), and sodium hydride (6.8 mg, 0.17 mmol) were added to N,N-dimethylformamide (3 mL), and the mixture was stirred at 80°C for 12 hours. After completion of the reaction, the reaction solution was concentrated, diluted with dichloromethane (10 mL), and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to obtain the target compound 287 (39.4 mg, 82%).

[0922] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 11.36 (s, 1H), 9.19 (d, J=2.3 Hz, 1H), 8.98 (d, J=2.3 Hz, 1H), 8.79 (dd, J=4.8, 1.7 Hz, 1H), 8.50 (dd, J=8.8, 2.4 Hz, 1H), 8.46-8.35 (m, 2H), 8.28 (s, 1H), 7.91 (dd, J=8.8, 1.4 Hz, 1H), 7.62-7.50 (m, 2H), 7.32 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=6.0 Hz, 2H), 1.58 (d, J=7.4 Hz, 4H).

[0923] MS(ESI, LR) Calculated for C 24 H 23N6O2[M+H] + : 427.2, found: 427.1.

[0924] Example 316. 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[0925] Example 355. (7-(6-(4-nitro-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0926] For Examples 316 and 355, the compounds were prepared by the same synthetic method as that used in Example 287, using compound 19 and the corresponding compounds. The structural and spectral data are shown in Table 17 below.

[0927] Table 17 Example Structure 1H NMR MS 316 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.92 (d, J=2.4 Hz, 1H), 8.45 (dd, J=8.9, 2.4 Hz, 1H), 8.25 (t, J=4.4 Hz, 2H), 7.90 (dd, J=8.9, 1.4 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 4.52 (t, J=8.0 Hz, 2H), 4.27 (dd, J=8.7, 7.3 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.70-1.62 (m, 2H), 1.57 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C21H22N5O3 [M+H]+: 392.2, found: 392.1. 355 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.55 (s, 1H), 9.13 (d, J=2.3 Hz, 1H), 8.80-8.60 (m, 2H), 8.29 (s, 1H), 8.21 (d, J=8.6 Hz, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.39 (dd, J=7.2, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (m, 2H), 1.63-1.44 (m, 4H). MS(ESI, LR) Calculated for C21H20N7O3 [M+H]+: 418.2, found: 418.1.

[0928] Example 301.N-(3-chloro-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide

[0929] Example 311. N-(3-chloro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide

[0930] For Examples 301 and 311, the compounds were prepared by the synthetic method described in Example 287 using compound 289 and the corresponding compounds. The structural and spectral data are shown in Table 18 below.

[0931] Table 18 Example Structure 1H NMR MS 301 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.19 (s, 1H), 9.19 (d, J=2.3 Hz, 1H), 9.02-8.97 (m, 1H), 8.82 (d, J=4.7 Hz, 1H), 8.76-8.71 (m, 1H), 8.41-8.35 (m, 1H), 8.30 (s, 1H), 7.96 (d, J=8.8 Hz, 1H), 7.62 (dd, J=7.9, 4.9 Hz, 1H), 7.56 (dd, J=8.9, 7.1 Hz, 1H), 7.43 (d, J=7.0 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (m, 3H), 1.58 (m, 4H). MS(ESI, LR) Calculated for C24H22ClN6O2 [M+H]+: 461.1, found: 461.0. 311 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.71 (s, 1H), 8.91 (d, J=2.1 Hz, 1H), 8.65 (d, J=2.1 Hz, 1H), 8.57 (d, J=2.2 Hz, 1H), 8.49 (dd, J=4.8, 1.7 Hz, 1H), 8.28 (s, 1H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.79 (dt, J=7.8, 2.1 Hz, 1H), 7.54 (dd, J=8.9, 7.1 Hz, 1H), 7.38 (ddd, J=7.2, 4.9, 3.1 Hz, 2H), 3.83 (s, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.3 Hz, 2H), 1.58 (t, J=6.7 Hz, 4H). MS(ESI, LR) Calculated for C25H24ClN6O2 [M+H]+: 475.2, found: 475.1.

[0932] Example 323. 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[0933] Example 362. N-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide

[0934] For Examples 323 and 362, the compounds were prepared by the synthetic method described in Example 287 using compound 288 and the corresponding compounds. The structural and spectral data are shown in Table 19 below.

[0935] Table 19 Example Structure 1H NMR MS 323 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.92-8.80 (m, 1H), 8.53 (dd, J=11.3, 1.9 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.38 (dd, J=7.1, 1.4 Hz, 1H), 4.60 (dd, J=8.6, 6.9 Hz, 2H), 4.25 (dd, J=8.4, 7.0 Hz, 2H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (m, 2H), 1.58 (m, 4H). MS(ESI, LR) Calculated for C21H21FN5O3 [M+H]+: 410.2, found: 410.1. 362 1H NMR (400 MHz, DMSO-d6) δ(ppm): 10.80 (s, 1H), 8.81 (dd, J=1.9, 0.9 Hz, 1H), 8.56 (d, J=2.3 Hz, 1H), 8.49 (dd, J=4.8, 1.7 Hz, 1H), 8.44 (dd, J=11.2, 1.9 Hz, 1H), 8.27 (s, 1H), 7.93 (dd, J=8.9, 1.3 Hz, 1H), 7.78 (dt, J=7.9, 2.0 Hz, 1H), 7.54 (dd, J=8.9, 7.1 Hz, 1H), 7.43-7.31 (m, 2H), 3.85 (s, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (m, 2H), 1.57 (m, 4H). MS(ESI, LR) Calculated for C25H24FN6O2 [M+H]+: 459.2, found: 459.1.

[0936] Example 308. 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-2-yl)oxazolidin-2-one

[0937]

[0938] The target compound 308 was obtained by the synthetic method described in Example 287 using compound 267 and oxazolidin-2-one.

[0939] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.30 (s, 2H), 8.27 (s, 1H), 7.93 (dd, J=8.9, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.38 (dd, J=7.1, 1.4 Hz, 1H), 4.48 (t, J=7.9 Hz, 2H), 4.27 (t, J=7.9 Hz, 2H), 3.62 (d, J=5.3 Hz, 4H), 1.73-1.63 (m, 2H), 1.58 (d, J=7.2 Hz, 4H).

[0940] MS(ESI, LR) Calculated for C 20 H 21 N6O3[M+H] + : 393.2, found: 393.1.

[0941] Example 257. (7-(2-(3-fluoroazetidin-1-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0942]

[0943] After obtaining the intermediate compound using compound 1-2 and (2-fluoro-4-pyridyl)boronic acid in the same synthetic method as in Step 1-3 in Example 1, the target compound 257 was obtained by the synthetic method described in Example 107 using azetidine.

[0944] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.65 (d, J=2.3 Hz, 1H), 8.23 ​​(s, 1H), 8.19 (dd, J=8.7, 2.4 Hz, 1H), 7.82 (dd, J=8.9, 1.4 Hz, 1H), 7.48 (dd, J=8.9, 7.1 Hz, 1H), 7.16 (dd, J=7.1, 1.4 Hz, 1H), 6.61 (d, J=8.8 Hz, 1H), 5.56 (ddt, J=57.4, 5.9, 2.9 Hz, 1H), 4.39 (dddd, J=21.3, 10.3, 5.9, 1.5 Hz, 2H), 4.12 (dddd, J=24.5, 10.4, 3.2, 1.5 Hz, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.4 Hz, 2H), 1.56 (d, J=7.6 Hz, 4H).

[0945] MS(ESI, LR) Calculated for C 21 H 23 FN5O [M+H] + : 380.2, found: 380.1.

[0946] Example 112.N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanesulfonamide

[0947] <Diagram 18>

[0948]

[0949] Compound 17 (0.1 g, 0.31 mmol) and triethylamine (97 μL, 0.7 mmol) were dissolved in dichloromethane (5 mL), the temperature was lowered to 0 °C using ice water, and methanesulfonyl chloride (52 μL, 0.7 mmol) was added dropwise. The temperature was slowly raised to room temperature, and the reaction mixture was stirred for 12 hours. After completion of the reaction, the reaction solution was diluted with dichloromethane (20 mL) and washed with water (30 mL), saturated aqueous sodium bicarbonate solution (30 mL), and saturated brine (30 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated using column chromatography to give the target compound 112 (29 mg, 24%).

[0950] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.80 (d, J=2.4 Hz, 1H), 8.33 (dd, J=8.7, 2.4 Hz, 1H), 8.25 (s, 1H), 7.88 (dd, J=8.9, 1.3 Hz, 1H), 7.51 (dd, J=8.9, 7.1 Hz, 1H), 7.24 (dd, J=7.0, 1.4 Hz, 1H), 7.12 (d, J=8.7 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 3.36 (s, 3H), 1.65 (d, J=7.5 Hz, 2H), 1.56 (d, J=7.6 Hz, 4H).

[0951] MS(ESI, LR) Calculated for C 20 H 22 N5O4S [M+H] + : 400.1, found: 400.0.

[0952] Example 113. (7-(3-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0953] <Diagram 19>

[0954]

[0955] Compound 6 (0.1 g, 0.3 mmol) was dissolved in N,N-dimethylformamide (8 mL). Sodium azide (0.039 g, 0.61 mmol) dissolved in water (2 mL) was added, and the mixture was stirred at 140°C for 12 hours. After completion of the reaction, the reaction solution was concentrated and separated using column chromatography to obtain the target compound 113 (7 mg, 6%).

[0956] 1 H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.51 (t,J=1.7 Hz, 1H), 8.25 (s, 1H), 8.12 (dt,J=7.7, 1.4 Hz, 1H), 7.89 (dd,J=7.7 Hz, 1.7 Hz), 7.7 (dt,J=7.7, 1.5 Hz, 1H), 7.55 (dt,J=10.8, 8.3 Hz, 2H), 7.20 (dd,J=7.0, 1.3 Hz, 1H), 3.64 (t,J=5.4 Hz, 4H), (c, 4H).

[0957] MS(ESI, LR) Calculated for C 20 H 20 N7O [M+H] + : 374.2, found: 374.2.

[0958] Example 114. (7-(4-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0959]

[0960] Target compound 114 was obtained by the synthesis method described in Example 113 using compound 15 and related compounds.

[0961] 1 H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.26 (s, 1H), 8.14 (d,J=8.1 Hz, 2H), 7.97 (d,J=9.2 Hz, 2H), 7.90-7.83 (m, 1H, 7.52 Hz), 7.90-7.83 (m, 1H, 7.8). Hz, 1H), 7.22 (d,J=7.0 Hz, 1H), 3.63 (t,J=5.4 Hz, 4H), 1.65 (s, 2H), 1.58 (s, 4H).

[0962] MS(ESI, LR) Calculated for C 20 H 20 N7O [M+H] + : 374.2, found: 374.2.

[0963] Example 115. 3-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

[0964] <Scheme 20>

[0965]

[0966] Step 115-1: After compound 6 (0.15 g, 0.45 mmol) was dissolved in ethanol (6.5 mL), hydroxyamine (47 mg, 0.68 mmol) was added and stirred at 80°C for 16 hours. After completion of the reaction, the reaction solution was concentrated, diluted with ethyl acetate (20 mL), and washed with water (10 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to give the target compound 115-1 (0.079 g, 24%).

[0967] Step 115-2: Compound 115-1 (0.2 g, 0.55 mmol) was dissolved in tetrahydrofuran (20 mL), and DIPEA (0.19 mL, 1.1 mmol) was added thereto. Triphosgene (0.065 g, 0.22 mmol) dissolved in tetrahydrofuran (5 mL) was slowly added to the reaction solution, which was stirred at room temperature for 30 minutes. The temperature was raised to 80 °C and stirred for 1 hour. After completion of the reaction, the reaction solution was concentrated and separated using column chromatography to give the target compound 115 (0.093 g, 43%).

[0968] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.36 (d,J=2.0 Hz, 1H), 8.26 (s, 1H), 8.09 (d,J=7.8 Hz, 1H), 7.94 (dd,J=15.0, 8.4 Hz, 2H), 7.71 (t,J=7.5 Hz, 1H), 7.55 (dd,J=8.9, 7.0 Hz, 1H), 7.24 (d,J=6.7 Hz, 1H), 6.53 (s, 1H), 3.63 (t,J=5.4 Hz, 3H), 1.65 (s, 2H), 1.57 (s, 4H).

[0969] MS(ESI, LR) Calculated for C 21 H 20 N5O3[M+H] + : 390.2, found: 390.1.

[0970] Example 116. 3-(4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

[0971] Example 117. 3-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-1,2,4-oxadiazol-5(4H)-one

[0972] Example 247. 3-[3-fluoro-5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-4H-1,2,4-oxadiazol-5-one

[0973] Example 275. 3-[2-fluoro-5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one

[0974] Example 295. 3-[3-fluoro-4-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one

[0975] Example 297. 3-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1,2,4-oxadiazol-5(4H)-one

[0976] Example 299. 3-(3-fluoro-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

[0977] Example 304. 3-[2-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one

[0978] Example 321. 3-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidin-2-yl]-4H-1,2,4-oxadiazol-5-one

[0979] Example 329. 3-(3-nitro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

[0980] Example 331. 3-(2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

[0981] For Examples 116, 117, 247, 275, 295, 297, 299, 304, 321, 329, and 331, compounds were obtained by successively using the synthetic method as in Step 1-3 of Example 1 and the synthetic method of Example 115, using compound 1-2 and the corresponding compounds. The structural and spectral data are shown in Table 20 below.

[0982] Table 20 Example Structure 1H NMR MS 116 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (d, J=4.8 Hz, 1H), 8.11 (d, J=7.9 Hz, 2H), 7.97 (d, J=7.9 Hz, 2H), 7.91 (d, J=8.9 Hz, 1H), 7.54 (t, J=8.1 Hz, 1H), 7.27 (d, J=7.1 Hz, 1H), 6.53 (s, 1H), 3.62 (d, J=5.3 Hz, 3H), 1.65 (s, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C21H20N5O3 [M+H]+: 390.2, found: 390.1. 117 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.27 (d, J=2.2 Hz, 1H), 8.64 (dd, J=8.3, 2.2 Hz, 1H), 8.28 (s, 1H), 8.17 (d, J=8.3 Hz, 1H), 7.97 (dd, J=8.8, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.41 (dd, J=7.0, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (s, 2H), 1.57 (s, 4H). MS(ESI, LR) Calculated for C20H19N6O3 [M+H]+: 391.1, found: 391.1. 247 1H NMR (400 MHz, DMSO-d6) δ(ppm): 13.36 (s, 1H), 9.19 (s, 1H), 8.70 (d, J=11.5 Hz, 1H), 8.31 (s, 1H), 8.00 (dd, J=8.9, 1.3 Hz, 1H), 7.59 (dd, J=8.9, 7.1 Hz, 1H), 7.50 (d, J=7.1 Hz, 1H), 3.63 (t, J=5.3 Hz, 4H), 1.66 (d, J=6.0 Hz, 2H), 1.57 (qt, J=5.4 Hz, 4H). MS(ESI, LR) Calculated for C20H18FN6O3 [M+H]+: 409.1, found: 409.1. 275 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.97 (s, 1H), 8.36 (dd, J=6.8, 2.3 Hz, 1H), 8.33-8.24 (m, 2H), 7.93 (dd, J=8.9, 1.3 Hz, 1H), 7.69 (dd, J=10.4, 8.8 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.5 Hz, 4H), 1.66 (q, J=5.7 Hz, 2H), 1.57 (q, J=5.7 Hz, 4H). MS(ESI, LR) Calculated for C21H19FN5O3 [M+H]+: 408.1, found: 408.1. 295 1H NMR (400 MHz, DMSO-d6) δ(ppm): 13.19 (s, 1H), 8.21 (s, 1H), 7.98 (dd, J=8.9, 1.4 Hz, 1H), 7.92 (t, J=7.5 Hz, 1H), 7.88-7.77 (m, 2H), 7.55 (dd, J=9.0, 7.0 Hz, 1H), 7.24 (dd, J=7.0, 1.4 Hz, 1H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.4 Hz, 2H), 1.57 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C21H19FN5O3 [M+H]+: 408.1, found: 408.1. 297 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.14 (d, J=2.2 Hz, 1H), 9.07 (d, J=2.0 Hz, 1H), 8.74 (t, J=2.1 Hz, 1H), 8.28 (s, 1H), 7.95 (dd, J=8.9, 1.4 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.36 (dd, J=6.9, 1.4 Hz, 1H), 3.63 (t, J=5.5 Hz, 4H), 1.69-1.62 (m, 2H), 1.58 (d, J=7.3 Hz, 4H). MS(ESI, LR) Calculated for C20H19N6O3 [M+H]+: 391.1, found: 391.1. 299 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.28 (s, 1H), 8.23 ​​(t, J=1.5 Hz, 1H), 8.04-7.99 (m, 1H), 7.94 (dd, J=9.0, 1.3 Hz, 1H), 7.74 (dd, J=9.1, 2.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.31 (dd, J=7.2, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.7 Hz, 2H), 1.58 (d, J=4.6 Hz, 4H). MS(ESI, LR) Calculated for C21H19FN5O3 [M+H]+: 408.1, found: 408.1. 304 1H NMR (400 MHz, DMSO-d6) δ(ppm): 13.01 (s, 1H), 8.28 (s, 1H), 8.15 (dd, J=12.0, 1.6 Hz, 1H), 8.01 (dd, J=8.2, 1.6 Hz, 1H), 7.96 (dt, J=7.9, 3.3 Hz, 2H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.41-7.33 (m, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.71-1.62 (m, 2H), 1.58 (q, J=5.6 Hz, 4H). MS(ESI, LR) Calculated for C21H19FN5O3 [M+H]+: 408.1, found: 408.1. 321 1H NMR (400 MHz, DMSO-d6) δ(ppm): 13.43 (s, 1H), 9.62 (s, 2H), 8.32 (s, 1H), 8.01 (dd, J=8.8, 1.4 Hz, 1H), 7.60 (dd, J=8.9, 7.0 Hz, 1H), 7.57-7.50 (m, 1H), 3.63 (t, J=5.3 Hz, 4H), 1.75-1.64 (m, 2H), 1.57 (d, J=7.9 Hz, 4H). MS(ESI, LR) Calculated for C19H18N7O3 [M+H]+: 392.1, found: 392.1. 329 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.09 (t, J=1.9 Hz, 1H), 8.79 (t, J=1.6 Hz, 1H), 8.77 (t, J=1.8 Hz, 1H), 8.33 (s, 1H), 8.00 (dd, J=8.9, 1.3 Hz, 1H), 7.59 (dd, J=8.9, 7.1 Hz, 1H), 7.45 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=7.4 Hz, 2H), 1.58 (d, J=7.3 Hz, 4H). MS(ESI, LR) Calculated for C21H19N6O5 [M+H]+: 435.1, found: 435.1. 331 1H NMR (400 MHz, DMSO-d6) δ(ppm): 13.10 (s, 1H), 8.30 (s, 1H), 8.08 (d, J=1.6 Hz, 1H), 8.06 (s, 1H), 7.98 (dd, J=9.0, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.1 Hz, 1H), 7.43 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.7 Hz, 2H), 1.57 (d, J=4.7 Hz, 4H). MS(ESI, LR) Calculated for C21H18F2N5O3 [M+H]+: 426.1, found: 426.1.

[0983] Example 118. (7-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0984] <Diagram 21>

[0985]

[0986] After compound 116-1 (0.014 g, 0.038 mmol) was dissolved in pyridine (2 mL), acetyl chloride (5.5 μL, 47 mg, 0.077 mmol) was added and stirred at 120 °C for 24 hours. After completion of the reaction, the reaction solution was diluted with ethyl acetate (10 mL) and washed with water (10 mL × 2) and saturated brine (10 mL × 2). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated using column chromatography to obtain the target compound 118 (5.4 mg, 36%).

[0987] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.27 (s, 1H), 8.20-8.11 (m, 4H), 7.92 (dd,J=8.8, 1.3 Hz, 1H), 7.54 (dd,J=8.9, 7.0 Hz, 1H), 7.28 (d,J=7.0 Hz, 1H), 3.63 (t,J=5.5 Hz, 4H), 2.71 (s, 3H), 1.65 (s, 2H), 1.57 (s, 4H).

[0988] MS(ESI, LR) Calculated for C 22 H 22 N5O2[M+H] + : 388.2, found: 388.1.

[0989] Example 263. [7-[5-fluoro-6-(5-methyl-1,2,4-oxadiazol-3-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0990] Example 276. [7-[4-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0991] Example 296. [7-[2-fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0992] Example 303. [7-[3-fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0993] Example 317. [7-[2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0994] Example 319. (7-(5-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0995] Example 322. (7-(3-fluoro-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0996] Example 328. (7-(3,5-difluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0997] Example 330. (7-(3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0998] For Examples 263, 276, 296, 303, 317, 319, 322, 328 and 330, compounds were obtained by sequentially using the same synthetic method as in Step 159-3 of Example 159, the synthetic method of Step 115-1 of Example 115 and the synthetic method of Example 118, using compound 1-2 and the corresponding compounds. The structural and spectral data are shown in Table 21 below.

[0999] Table 21 Example Structure 1H NMR MS 263 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.20 (t, J=1.6 Hz, 1H), 8.70 (dd, J=11.5, 1.8 Hz, 1H), 8.32 (s, 1H), 8.00 (dd, J=8.9, 1.4 Hz, 1H), 7.59 (dd, J=8.8, 7.1 Hz, 1H), 7.51 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.75 (s, 3H), 1.66 (d, J=5.6 Hz, 2H), 1.58 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C21H20FN6O2 [M+H]+: 407.2, found: 407.1. 276 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.62 (dd, J=6.8, 2.4 Hz, 1H), 8.28 (s, 1H), 8.19 (ddd, J=8.7, 4.8, 2.4 Hz, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.66 (dd, J=10.5, 8.7 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.71 (s, 3H), 1.66 (d, J=5.6 Hz, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C22H21FN5O2 [M+H]+: 406.2, found: 406.1. 296 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.22 (s, 1H), 8.06-7.86 (m, 4H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.24 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.73 (s, 3H), 1.65 (d, J=7.0 Hz, 2H), 1.62-1.51 (m, 4H). MS(ESI, LR) Calculated for C22H21FN5O2 [M+H]+: 406.2, found: 406.1. 303 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.30 (s, 1H), 8.18 (t, J=7.8 Hz, 1H), 8.13 (d, J=12.0 Hz, 1H), 8.01 (d, J=8.2 Hz, 1H), 7.95 (d, J=8.9 Hz, 1H), 7.55 (t, J=8.0 Hz, 1H), 7.37 (d, J=7.1 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.80-2.67 (m, 3H), 1.66 (d, J=6.6 Hz, 2H), 1.58 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C22H21FN5O2 [M+H]+: 406.2, found: 406.1. 317 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.53 (s, 2H), 8.11 (dd, J=9.0, 1.3 Hz, 1H), 8.09 (s, 1H), 7.43 (dd, J=9.0, 7.0 Hz, 1H), 7.15-7.09 (m, 1H), 3.73 (t, J=5.3 Hz, 4H), 2.77 (s, 3H), 1.79-1.72 (m, 2H), 1.72-1.65 (m, 4H). MS(ESI, LR) Calculated for C20H20N7O2 [M+H]+: 390.2, found: 390.1. 319 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.27 (dd, J=8.0, 2.1 Hz, 2H), 9.00 (t, J=2.1 Hz, 1H), 8.30 (s, 1H), 7.97 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.43 (dd, J=7.0, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 2.73 (s, 3H), 1.66 (d, J=5.7 Hz, 2H), 1.63-1.55 (m, 4H). MS(ESI, LR) Calculated for C21H21N6O2 [M+H]+: 389.2, found: 389.1. 322 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.46 (t, J=1.5 Hz, 1H), 8.30 (s, 1H), 8.07 (dt, J=9.6, 2.1 Hz, 1H), 7.97-7.89 (m, 2H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.36 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 2.71 (s, 3H), 1.66 (d, J=5.0 Hz, 2H), 1.58 (s, 4H). MS(ESI, LR) Calculated for C22H21FN5O2 [M+H]+: 406.2, found: 406.1. 328 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.32 (s, 1H), 8.04 (d, J=9.6 Hz, 2H), 7.98 (dd, J=8.9, 1.4 Hz, 1H), 7.59-7.54 (m, 1H), 7.44 (d, J=7.0 Hz, 1H), 3.64 (d, J=5.7 Hz, 4H), 2.75 (s, 3H), 1.66 (s, 2H), 1.58 (s, 4H). MS(ESI, LR) Calculated for C22H20F2N5O2 [M+H]+: 424.2, found: 424.1. 330 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.01 (t, J=1.9 Hz, 1H), 8.98 (t, J=1.6 Hz, 1H), 8.82 (t, J=1.9 Hz, 1H), 8.33 (s, 1H), 7.99 (dd, J=8.9, 1.4 Hz, 1H), 7.58 (dd, J=8.9, 7.1 Hz, 1H), 7.48 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 2.75 (s, 3H), 1.66 (d, J=7.3 Hz, 2H), 1.58 (s, 4H). MS(ESI, LR) Calculated for C22H21N6O4 [M+H]+: 433.2, found: 433.1.

[1000] Example 352. [7-[4-(1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1001] <Diagram 22>

[1002]

[1003] Compound 116-1 (50 mg, 0.14 mmol) was added to trimethyl orthoformate (0.13 mL, 0.78 mmol) and stirred at 100°C for 16 hours. The reaction solution was concentrated and separated using column chromatography to obtain the target compound 352 (35 mg, 65%).

[1004] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.78 (s, 1H), 8.27 (s, 1H), 8.22 (d, J=8.5 Hz, 2H), 8.17 (d, J=8.5 Hz, 2H), 7.93 (dd, J=8.8, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.28 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.2 Hz, 2H), 1.58 (s, 4H).

[1005] MS(ESI, LR) Calculated for C 21 H 20 N5O2[M+H] + : 374.2, found: 374.1.

[1006] Example 341. (7-(3-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1007] Example 342. (7-(3-nitro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1008] Example 374. (7-(5-(1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1009] For Examples 341, 342, and 374, compounds were obtained by successively using the same synthetic method as in Step 159-3 of Example 159, the synthetic method of Step 115-1 of Example 115, and the synthetic method of Example 352, using compound 1-2 and the corresponding compounds. The structural and spectral data are shown in Table 22 below.

[1010] Table 22 Example Structure 1H NMR MS 341 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.81 (s, 1H), 8.51 (t, J=1.5 Hz, 1H), 8.29 (s, 1H), 8.09 (dt, J=9.8, 2.2 Hz, 1H), 7.97 (ddd, J=9.0, 7.9, 1.8 Hz, 2H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.37 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.5 Hz, 2H), 1.58 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C21H19FN5O2 [M+H]+: 392.1, found: 392.1. 342 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.89 (s, 1H), 9.03 (p, J=1.7 Hz, 2H), 8.86 (t, J=1.9 Hz, 1H), 8.32 (s, 1H), 8.00 (dd, J=8.9, 1.4 Hz, 1H), 7.59 (dd, J=8.9, 7.0 Hz, 1H), 7.49 (dd, J=7.1, 1.4 Hz, 1H), 3.65 (t, J=5.4 Hz, 4H), 1.67 (d, J=5.6 Hz, 2H), 1.58 (d, J=7.7 Hz, 4H). MS(ESI, LR) Calculated for C21H19N6O4 [M+H]+: 419.1, found: 419.0. 374 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.86 (s, 1H), 9.33 (d, J=2.0 Hz, 1H), 9.28 (d, J=2.2 Hz, 1H), 9.05 (t, J=2.1 Hz, 1H), 8.30 (s, 1H), 7.97 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.1 Hz, 1H), 7.44 (dd, J=7.0, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.5 Hz, 2H), 1.58 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C20H19N6O2 [M+H]+: 375.1, found: 375.1.

[1011] Example 361. 1-piperidyl-[7-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[1012] <Diagram 23>

[1013]

[1014] Compound 116-1 (0.040 g, 0.11 mmol) was dissolved in tetrahydrofuran (2 mL), trifluoroacetic anhydride (15.3 μL, 23 mg, 0.11 mmol) was added, and the mixture was stirred at 80 °C for 16 hours. After completion of the reaction, the reaction solution was diluted with dichloromethane (10 mL) and washed with water (10 mL × 2) and saturated brine (10 mL × 2). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated using column chromatography to obtain the target compound 361 (45 mg, 92%).

[1015] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.28 (s, 1H), 8.27-8.19 (m, 4H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.1 Hz, 1H), 7.31 (dd, J=7.0, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.0 Hz, 2H), 1.62-1.51 (m, 4H).

[1016] MS(ESI, LR) Calculated for C 22 H 19 F3N5O2[M+H] + : 442.1, found: 442.1.

[1017] Example 359. [7-[4-(5-amino-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1018] <Diagram 24>

[1019]

[1020] Step 359-1: The target compound 359-1 was obtained by the same synthetic method as in Example 361 using compound 116-1 and trichloroacetic anhydride.

[1021] Step 359-2: To compound 359-1 (130 mg, 0.26 mmol) was added 7 N ammonia solution in methanol (1.6 mL, 11.2 mmol), and stirred at room temperature for 16 hours. After concentrating the reaction solution, it was separated using column chromatography to obtain the target compound 359 (92 mg, 89%).

[1022] 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.26 (s, 1H), 8.09 (d,J=8.6 Hz, 2H), 8.04 (d,J=8.6 Hz, 2H), 8.01 (s, 2H), 7.91 (dd,J=8.6 Hz, 2H), 7.91 (dd,J=8.6 Hz, H 7.54 (dd,J=8.9, 7.1 Hz, 1H), 7.26 (dd,J=7.1, 1.4 Hz, 1H), 3.63 (t,J=5.4 Hz, 4H), 1.65 (d,J=5.1 Hz, 2H), 1.57 (s, 4H).

[1023] MS(ESI, LR) Calculated for C 21 H 21 N6O2[M+H] + : 389.2, found: 389.1.

[1024] Example 348. [7-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1025] <Scheme 25>

[1026]

[1027] Step 348-1: Compound 10 (120 mg, 0.34 mmol) was dissolved in dichloromethane (4 mL), tert-butyl carbazate (49.9 mg, 0.38 mmol) and EDC⋅HCl (72.4 mg, 0.38 mmol) were added, and stirred for 1 hour. After completion of the reaction, the mixture was diluted with dichloromethane (10 mL), washed with aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give compound 348-1 (151 mg, 95%).

[1028] Step 348-2: Compound 348-1 (220 g, 0.47 mmol) was placed in a reaction vessel, and the temperature was lowered to 0°C. Trifluoroacetic acid (1 mL, 13.1 mmol) was added, and the mixture was stirred for 1 hour. After completion of the reaction, the mixture was concentrated, diluted with diethyl ether (10 mL), recrystallized, and filtered. The filtrate was dissolved in aqueous sodium bicarbonate solution and extracted with dichloromethane. Drying over anhydrous magnesium sulfate, filtration, and concentration were performed to obtain compound 348-2 (140 mg, 65%).

[1029] Step 348-3: N,N-dimethylformamide (2 mL) was added to the reaction vessel, 4 N hydrochloric acid solution dissolved in 1,4-dioxane (0.1 mL, 0.41 mmol) was added, and stirring was carried out for 5 min. Imidazole (28.1 mg, 0.41 mmol) was added, and stirring was carried out for 30 min, compound 348-2 (50 mg, 0.14 mmol) was added, and stirring was carried out at 100 °C for 16 h. Phosphorus oxychloride (15.4 μL, 0.17 mmol) was added, and stirring was carried out for 12 h. After completion of the reaction, the temperature was lowered to room temperature, diluted with saturated brine (5 mL), and extracted with dichloromethane (5 mL × 3). The combined organic layers were dried over anhydrous magnesium sulfate, filtered, concentrated and recrystallized using N,N-dimethylformamide, filtered and dried to give the title compound 348 (14 mg, 26%).

[1030] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.27 (s, 1H), 8.23-8.10 (m, 4H), 7.93 (dd,J=8.9, 1.3 Hz, 1H), 7.58-7.51 (m, 1H), 7.29 (dd,J=7.0, 1.4 Hz, 1H), 3.63 (t,J=5.4 Hz, 4H), 2.63 (s, 3H), 1.66 (s, 2H), 1.62-1.53 ​​(m, 4H).

[1031] MS(ESI, LR) Calculated for C 22 H 22 N5O2[M+H] + : 388.2, found: 388.1.

[1032] Example 364. [7-[6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1033] Example 379. [7-[5-fluoro-6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1034] For Examples 364 and 379, compounds were obtained by successively using the same synthetic method as in Step 159-3 of Example 159 and the same synthetic method as in Example 348, using the corresponding compounds. The structural and spectral data are shown in Table 23 below.

[1035] Table 23 Example Structure 1H NMR MS 364 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.32-9.27 (m, 1H), 8.68 (dd, J=8.3, 2.2 Hz, 1H), 8.34 (dd, J=8.2, 0.8 Hz, 1H), 8.30 (s, 1H), 7.97 (dd, J=8.9, 1.3 Hz, 1H), 7.58 (dd, J=8.9, 7.1 Hz, 1H), 7.42 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.66 (s, 3H), 1.66 (d, J=5.3 Hz, 2H), 1.58 (d, J=7.0 Hz, 4H). MS(ESI, LR) Calculated for C21H21N6O2 [M+H]+: 389.2, found: 389.1. 379 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.22 (d, J=1.6 Hz, 1H), 8.74 (dd, J=11.6, 1.7 Hz, 1H), 8.33 (s, 1H), 8.00 (dd, J=8.8, 1.4 Hz, 1H), 7.59 (dd, J=8.8, 7.1 Hz, 1H), 7.51 (dd, J=7.1, 1.5 Hz, 1H), 3.64 (t, J=5.3 Hz, 4H), 2.68 (s, 3H), 1.66 (s, 2H), 1.58 (d, J=7.1 Hz, 4H). MS(ESI, LR) Calculated for C21H20FN6O2 [M+H]+: 407.2, found: 407.1.

[1036] Example 350. [7-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1037] Example 380. [7-[5-fluoro-6-(1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1038] For Examples 350 and 380, compounds were obtained by sequentially using the same synthetic method as in Step 348-1, 348-2 of Example 348 and in Example 352 using compounds 10 and 243. The structural and spectral data are shown in Table 24 below.

[1039] Table 24 Example Structure 1H NMR MS 350 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.42 (s, 1H), 8.27 (s, 1H), 8.24-8.17 (m, 4H), 7.94 (dd, J=8.9, 1.3 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.30 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.6 Hz, 2H), 1.58 (s, 4H). MS(ESI, LR) Calculated for C21H20N5O2 [M+H]+: 374.2, found: 374.1. 380 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.56 (s, 1H), 9.25 (t, J=1.5 Hz, 1H), 8.77 (dd, J=11.6, 1.7 Hz, 1H), 8.33 (s, 1H), 8.01 (dd, J=8.8, 1.4 Hz, 1H), 7.59 (dd, J=8.8, 7.1 Hz, 1H), 7.52 (dd, J=7.1, 1.4 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.7 Hz, 2H), 1.58 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C20H18FN6O2 [M+H]+: 393.1, found: 393.1.

[1040] Example 365 1-piperidyl-[7-[6-(2-thioxo-3H-1,3,4-oxadiazol-5-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[1041] <Diagram 26>

[1042]

[1043] Step 365-1: The target compound 365-1 was obtained in the same synthetic method as in Step 1-3 in Example 1 using compound 1-2.

[1044] Step 365-2: The target compound 365-2 was obtained in the same synthetic method as in Step 243-1 in Example 243 using compound 365-1.

[1045] Step 365-3: The target compound 365-3 was obtained in the same synthetic method as in Step 348-1 in Example 348 using compound 365-2.

[1046] Step 365-4: The target compound 365-4 was obtained in the same synthetic method as in Step 348-2 in Example 348 using compound 365-3.

[1047] Step 365-5: Compound 365-4 (70 mg, 0.15 mmol) was dissolved in 1,4-dioxane (2 mL), di(imidazol-1-yl)methanethione (39.5 mg, 0.22 mmol) and DBU (88 μL, 0.59 mmol) were added, and the mixture was stirred at 100°C for 16 hours. After completion of the reaction, the reaction solution was concentrated and separated using column chromatography to obtain the target compound 365 (57 mg, 95%).

[1048] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.81 (s, 1H), 9.20 (d, J=2.2 Hz, 1H), 8.62 (dd, J=8.2, 2.2 Hz, 1H), 8.28 (s, 1H), 8.24 (d, J=8.2 Hz, 1H), 7.95 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.0 Hz, 1H), 7.41 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.5 Hz, 4H), 1.65 (d, J=5.3 Hz, 2H), 1.59 (d, J=4.7 Hz, 4H).

[1049] MS(ESI, LR) Calculated for C 20 H 19 N6O2S [M+H] + : 407.1, found: 407.1.

[1050] Example 394. [7-[5-fluoro-6-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1051] <Diagram 27>

[1052]

[1053] Step 394-1: The target compound 394-1 was obtained in the same synthetic method as in Steps 348-1 and 348-2 in Example 348, using compound 243.

[1054] Step 394-2: The target compound 394-2 was obtained in the same synthetic method as in Example 361 using compound 394-1.

[1055] Step 394-3: Compound 394-2 (75 mg, 0.15 mmol) was dissolved in 1,4-dioxane (2 mL), phosphorus oxychloride (0.15 mL, 1.5 mmol) was added, and the mixture was stirred at 100°C for 16 hours. After completion of the reaction, the reaction solution was concentrated, diluted with dichloromethane (5 mL), and the pH of the solution was adjusted to 9 with aqueous sodium bicarbonate solution. After extraction with dichloromethane (5 mL × 3), the combined organic solution was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated using column chromatography to give the target compound 394 (7 mg, 9.2%).

[1056] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.29 (t, J=1.5 Hz, 1H), 8.83 (dd, J=11.6, 1.7 Hz, 1H), 8.33 (s, 1H), 8.02 (dd, J=8.8, 1.5 Hz, 1H), 7.60 (dd, J=8.8, 7.1 Hz, 1H), 7.57-7.52 (m, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (d, J=6.1 Hz, 2H), 1.58 (d, J=4.6 Hz, 4H).

[1057] MS(ESI, LR) Calculated for C 21 H 17F4N6O2[M+H] + : 461.1, found: 461.1.

[1058] Example 349. 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-3H-1,3,4-oxadiazol-2-one

[1059] <Diagram 28>

[1060]

[1061] Compound 348-2 (50 mg, 0.14 mmol) was dissolved in tetrahydrofuran (2 mL), and DIPEA (48 μL, 0.28 mmol) and triphosgene (16.3 mg, 0.05 mmol) were added and stirred at 80°C for 1 hour. After completion of the reaction, the reaction solution was concentrated and separated using column chromatography to obtain the target compound 349 (30 mg, 53%).

[1062] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 12.69 (s, 1H), 8.26 (s, 1H), 8.17-8.09 (m, 2H), 8.00-7.94 (m, 2H), 7.92 (dd, J=8.9, 1.4 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (q, J=6.2 Hz, 2H), 1.57 (q, J=5.7 Hz, 4H).

[1063] MS(ESI, LR) Calculated for C 21 H 20N5O3[M+H] + : 390.1, found: 390.1.

[1064] Example 360. 5-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one

[1065] Example 373. 5-[3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one

[1066] For Examples 360 and 373, the compounds were prepared in the same synthetic manner as in Example 349 using the corresponding compounds. The structural and spectral data are shown in Table 25 below.

[1067] Table 25 Example Structure 1H NMR MS 360 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.88 (s, 1H), 9.24 (d, J=2.2 Hz, 1H), 8.62 (dd, J=8.3, 2.2 Hz, 1H), 8.29 (s, 1H), 8.10 (d, J=8.3 Hz, 1H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.57 (dd, J=8.9, 7.1 Hz, 1H), 7.39 (dd, J=7.1, 1.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.72-1.62 (m, 2H), 1.62-1.51 (m, 4H). MS(ESI, LR) Calculated for C20H19N6O3 [M+H]+: 391.1, found: 391.1. 373 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.98 (s, 1H), 9.16 (t, J=1.6 Hz, 1H), 8.67 (dd, J=11.9, 1.7 Hz, 1H), 8.32 (s, 1H), 7.99 (dd, J=8.9, 1.4 Hz, 1H), 7.58 (dd, J=8.8, 7.1 Hz, 1H), 7.49 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.5 Hz, 4H), 1.71-1.63 (m, 2H), 1.58 (q, J=5.7 Hz, 4H). MS(ESI, LR) Calculated for C20H18FN6O3 [M+H]+: 409.1, found: 409.1.

[1068] Example 300. [7-[4-(2-methylpyrazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1069] Example 302. [7-[4-(3-furyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1070] Example 305. 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carbonitrile

[1071] Example 306. [7-[4-(2-hydroxypyrimidin-5-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1072] Example 307. 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carboxamide

[1073] Example 324. [7-[4-(3,5-dimethylisoxazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1074] Example 346. 1-piperidyl-[7-[4-(1H-pyrazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[1075] Example 347. 1-piperidyl-[7-[4-(3-thienyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[1076] For Examples 300, 302, 305, 306, 307, 324, 346, and 347, compounds were obtained using the same synthetic method as in Step 1-3 in Example 1, using compound 292 and the corresponding compounds. The structural and spectral data are shown in Table 26 below.

[1077] Table 26 Example Structure 1H NMR MS 300 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (s, 1H), 8.07 (d, J=8.0 Hz, 2H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.74 (d, J=8.1 Hz, 2H), 7.58-7.50 (m, 2H), 7.25 (d, J=7.0 Hz, 1H), 6.53 (d, J=1.9 Hz, 1H), 3.95 (s, 3H), 3.63 (t, J=5.3 Hz, 4H), 1.66 (d, J=4.9 Hz, 2H), 1.58 (d, J=6.4 Hz, 4H). MS(ESI, LR) Calculated for C23H24N5O [M+H]+: 386.2, found: 386.1. 302 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.34-8.31 (m, 1H), 8.25 (d, J=5.8 Hz, 1H), 8.01-7.95 (m, 2H), 7.88 (dd, J=8.9, 1.4 Hz, 1H), 7.83-7.78 (m, 3H), 7.52 (dd, J=8.8, 7.0 Hz, 1H), 7.21 (dd, J=7.1, 1.4 Hz, 1H), 7.09-7.05 (m, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (s, 2H), 1.57 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C23H22N3O2 [M+H]+: 372.2, found: 372.1. 305 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.51 (s, 2H), 8.26 (s, 1H), 8.16 (d, J=8.4 Hz, 2H), 8.12 (d, J=8.4 Hz, 2H), 7.92 (d, J=8.8 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.28 (d, J=7.0 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.3 Hz, 2H), 1.58 (d, J=7.7 Hz, 4H). MS(ESI, LR) Calculated for C24H21N6O [M+H]+: 409.2, found: 409.1. 306 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.29 (s, 1H), 8.75 (s, 2H), 8.24 (s, 1H), 8.02 (d, J=8.4 Hz, 2H), 7.88 (d, J=8.9 Hz, 1H), 7.83 (d, J=8.2 Hz, 2H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.22 (d, J=7.0 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.1 Hz, 2H), 1.57 (d, J=7.6 Hz, 4H). MS(ESI, LR) Calculated for C23H22N5O2 [M+H]+: 400.2, found: 400.2. 307 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.38 (s, 2H), 8.26 (s, 2H), 8.14 (d, J=8.1 Hz, 2H), 8.09 (d, J=8.2 Hz, 2H), 7.96-7.89 (m, 1H), 7.85 (s, 1H), 7.55 (dd, J=9.0, 7.1 Hz, 1H), 7.28 (d, J=6.9 Hz, 1H), 3.64 (t, J=5.4 Hz, 4H), 1.66 (s, 2H), 1.58 (s, 4H). MS(ESI, LR) Calculated for C24H23N6O2 [M+H]+: 427.2, found: 427.1. 324 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (s, 1H), 8.04 (d, J=8.2 Hz, 2H), 7.90 (dd, J=8.9, 1.4 Hz, 1H), 7.59 (d, J=8.1 Hz, 2H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.27-7.21 (m, 1H), 3.63 (t, J=5.4 Hz, 4H), 2.49 (s, 3H), 2.31 (s, 3H), 1.66 (d, J=7.5 Hz, 2H), 1.57 (d, J=7.5 Hz, 4H). MS(ESI, LR) Calculated for C24H25N4O2 [M+H]+: 401.2, found: 401.1. 346 1H NMR (400 MHz, DMSO-d6) δ(ppm): 13.04 (s, 1H), 8.31 (s, 1H), 8.24 (s, 1H), 8.05 (s, 1H), 7.95 (d, J=8.1 Hz, 2H), 7.87 (dd, J=8.9, 1.4 Hz, 1H), 7.79 (d, J=8.1 Hz, 2H), 7.51 (dd, J=8.9, 7.0 Hz, 1H), 7.20 (dd, J=7.0, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (s, 2H), 1.58 (d, J=7.4 Hz, 4H). MS(ESI, LR) Calculated for C22H22N5O [M+H]+: 372.2, found: 372.1. 347 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (s, 1H), 8.06-7.97 (m, 3H), 7.94-7.86 (m, 3H), 7.71 (dd, J=5.0, 2.8 Hz, 1H), 7.67 (dd, J=5.0, 1.5 Hz, 1H), 7.52 (dd, J=8.9, 7.1 Hz, 1H), 7.23 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=5.5 Hz, 2H), 1.58 (d, J=7.2 Hz, 4H). MS(ESI, LR) Calculated for C23H22N3OS [M+H]+: 388.1, found: 388.1.

[1078] Example 351. [7-[4-(5-methylthiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1079] <Diagram 29>

[1080]

[1081] Step 351-1: Compound 292 (0.370 g, 0.96 mmol) was dissolved in N,N-dimethylformamide (10 mL), and bis(pinacolato)diboron (0.366 g, 1.44 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.040 g, 0.05 mmol), and potassium acetate (0.283 g, 2.89 mmol) were added. The reaction solution was bubbled with nitrogen for 10 min and stirred at 90 °C for 16 h. After completion of the reaction, the temperature was lowered to room temperature, diluted with dichloromethane (10 mL), and palladium was removed using diatomaceous earth (Celite). The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated using column chromatography to afford the target compound 351-1 (0.528 g, 57%).

[1082] Step 351-2: The target compound 351 was obtained in the same synthetic method as in Step 159-3 of Example 159 using compound 351-1 and 2-bromo-5-methylthiazole.

[1083] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (s, 1H), 8.13-8.01 (m, 4H), 7.91 (dd, J=8.8, 1.3 Hz, 1H), 7.69 (d, J=1.5 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.26 (dd, J=7.1, 1.4 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.66 (d, J=6.8 Hz, 2H), 1.58 (d, J=5.0 Hz, 4H).

[1084] MS(ESI, LR) Calculated for C 23 H 23 N4OS [M+H] + : 403.2, found: 403.1.

[1085] Example 358. 7-[4-(1,2-dimethylimidazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1086]

[1087] The target compound 358 was obtained in the same synthetic method as in Step 351-2 in Example 351, using compound 351-1 and 4-bromo-1,2-dimethylimidazole.

[1088] 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.07 (s, 1H), 7.93 (d,J=8.8 Hz, 1H), 7.87 (s, 4H), 7.36 (dd,J=8.9, 7.0 Hz, 1H, 1H, 7.7), (6, 17H), (d,J=7.1 Hz, 1H), 3.72 (t,J=5.3 Hz, 4H), 3.62 (s, 3H), 2.45 (s, 3H), 1.72 (sq.,J=5.6 Hz, 2H), 1.69-1.62 (m, 4H).

[1089] MS(ESI, LR) Calculated for C 24 H 26 N5O [M+H] + : 400.2, found: 400.1.

[1090] Example 343. (7-(3-amino-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1091]

[1092] Target compound 343 was obtained by the same synthesis method as in Example 7, using compound 330.

[1093] 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.24 (s, 1H), 7.88 (dd,J=8.9, 1.3 Hz, 1H), 7.64 (t,J=1.5 Hz, 1H), 7.50 (dd,J=8.9, 7.9 Hz, 1H), 7.9 (t,J=1.9 Hz, 1H), 7.25 (t,J=1.9 Hz, 1H), 7.14 (dd,J=7.1, 1.4 Hz, 1H), 5.64 (s, 2H), 3.63 (t,J=5.4 Hz, 4H), 2.66 (s, 38 Hz, 1.6H), 2H), 1.62-1.55 (m, 4H).

[1094] MS(ESI, LR) Calculated for C 22 H 23 N6O2[M+H] + : 403.2, found: 403.1.

[1095] Example 119. (Z)-5-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzylidene)thiazolidine-2,4-dione

[1096] <Scheme 30>

[1097]

[1098] Step 119-1: Target compound 119-1 was obtained by the same synthesis method as in steps 1-3 in Example 1, using compound 1-2 and 3-formylphenylboronic acid.

[1099] Step 119-2: Compound 119-1 (0.15 g, 0.45 mmol) and thiazolidine-2,4-dione (0.063 g, 0.54 mmol) were dissolved in ethanol (5 mL), piperidine (35 μL, 0.36 mmol) was added, and the mixture was stirred at 80°C for 16 hours. After completion of the reaction, the temperature was lowered to room temperature, diluted with water (5 mL), and acidified with 1 N citric acid solution (pH 4) to obtain a precipitated solid. The solid was filtered and washed successively with water, diethyl ether, and methyl tert-butyl ether to give the target compound 119 (50 mg, 25%).

[1100] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.09-8.04 (m, 2H), 8.01-7.83 (m, 3H), 7.67-7.64 (m, 2H), 7.45 (td, J=8.7, 4.4 Hz, 1H), 7.06-6.96 (m, 1H), 3.76-3.72 (m, 4H), 1.76-1.69 (m, 6H).

[1101] MS(ESI, LR) Calculated for C 23 H 21 N4O3S [M+H] + : 433.1, found: 433.1.

[1102] Example 253. 3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzaldehyde oxime

[1103]

[1104] Target compound 253 was obtained by the synthesis method of step 236-2 of Example 236 using compound 119-1.

[1105] 1 H NMR (400 MHz, DMSO-d6) δ(m.d.): 11.35 (s, 1H), 8.16 (t,J=1.8 Hz, 1H), 7.94-7.87 (m, 2H), 7.76 (dt,J=7.9, 1.4 Hz, 1.7,7.6 H), 4H), 7.20 (dd,J=7.1, 1.4 Hz, 1H), 3.63 (t,J=5.4 Hz, 4H), 1.65 (sq.,J=5.7 Hz, 2H), 1.57 (sq.,J=7.6 Hz, 4H).

[1106] MS(ESI, LR) Calculated for C 20 H 21 N4O2[M+H] + : 349.2, found: 349.1.

[1107] Example 132. 2-methyl-7-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1108] <Scheme 31>

[1109]

[1110] Compound 131 (30 mg, 0.08 mmol) was dissolved in N,N-dimethylformamide (3 mL), the temperature was lowered to 0 °C, and sodium hydride (60%, 8 mg, 0.2 mmol) was added. The reaction solution was stirred at room temperature for 15 min, methyl iodide (7.5 μL, 0.12 mmol) was added, and the mixture was stirred for 1 hour. After completion of the reaction, the temperature was lowered to 0 °C, and the reaction solution was diluted with water (10 mL) and extracted with dichloromethane (10 mL × 3). The combined organic layers were washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated using column chromatography to give the target compound 132 (13.8 mg, 44%).

[1111] 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.41 (d,J=2.0 Hz, 1H), 8.24 (s, 1H), 8.00 (dd,J=7.9, 2.0 Hz, 1H), 7.89 (dd,J=7.9, 1.4 Hz, 1H), 7.55-7.45 (m, 2H), 7.19 (dd,J=7.0, 1.4 Hz, 1H), 3.63 (t,J=5.5 Hz, 6H), 3.08 (d,J=7.4 Hz, 5H), 1.69-1.62 (m, 2.6), 1.5H (1.5H).

[1112] MS(ESI, LR) Calculated for C 23 H 25 N4O2[M+H] + : 389.2, found: 389.2.

[1113] Example 199. 6-methyl-3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

[1114]

[1115] Target compound 199 was obtained by the synthesis method described in Example 132 using compound 195 and corresponding compounds.

[1116] 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 9.09 (d,J=2.3 Hz, 1H), 8.78 (d,J=2.3 Hz, 1H), 8.27 (s, 1H), 7.93 (dd,J=8.9 Hz, 1.4 Hz, 1.5H), 7.5 (dd,J=8.9, 7.1 Hz, 1H), 7.33 (dd,J=7.1, 1.3 Hz, 1H), 3.73 (t,J=6.8 Hz, 2H), 3.63 (t,J=5.4 Hz, 4H), 3.24 (t,J=5.4 Hz, 4H), 3.24 (t,J=6.8 Hz, 3,3H), H 1.66 (e,J=6.1 Hz, 2H), 1.57 (e,J=7.3 Hz, 4H).

[1117] MS(ESI, LR) Calculated for C 22 H 24 N5O2[M+H] + : 390.2, found: 390.1.

[1118] Example 133. 2-isopropyl-7-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1119] <Scheme 32>

[1120]

[1121] Target compound 133 was obtained by the synthesis method described in Example 132 using compound 131 and isopropyl iodide.

[1122] 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.41 (d,J=2.0 Hz, 1H), 8.24 (s, 1H), 7.98 (dd,J=7.9, 2.0 Hz, 1H), 7.88 (dd,J=7.9, 1.3 Hz, 1H), 7.54-7.46 (m, 2H), 7.19 (dd,J=7.0, 1.4 Hz, 1H), 4.89 (p,J=6.8 Hz, 1H), 3.63 (t,J=5.4 Hz, 4H), 3.50 (t,J=6.5 Hz, 4H), 3.50 (t,J=6.5 Hz, 2H), 2H), 1.65 (s, 2H), 1.57 (s, 4H), 1.17 (d,J=6.8 Hz, 6H).

[1123] MS(ESI, LR) Calculated for C 25 H 29 N4O2[M+H] + : 417.2, found: 417.1.

[1124] Example 135. 2-methyl-7-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one

[1125]

[1126] Target compound 135 was obtained by the synthesis method described in Example 132 using compound 134 and methyl iodide.

[1127] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.80 (d, J=1.9 Hz, 1H), 8.27 (s, 1H), 8.23 ​​(dd, J=8.3, 2.0 Hz, 1H), 7.91 (dd, J=8.9, 1.3 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 7.60 (d, J=7.3 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.28 (dd, J=7.1, 1.4 Hz, 1H), 6.72 (d, J=7.3 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 3.55 (s, 3H), 1.65 (d, J=7.8 Hz, 2H), 1.57 (d, J=7.7 Hz, 4H).

[1128] MS(ESI, LR) Calculated for C 23 H 23 N4O2[M+H] + : 387.2, found: 387.1.

[1129] Example 137. 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1130]

[1131] The target compound 137 was obtained by the synthetic method described in Example 132 using compound 136 and methyl iodide.

[1132] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (s, 1H), 8.04-7.99 (m, 1H), 7.93-7.86 (m, 3H), 7.52 (dd,J=8.9, 7.0 Hz, 1H), 7.22 (dd,J=7.1, 1.4 Hz, 1H), 3.62 (t,J=5.5 Hz, 6H), 3.08 (s, 5H), 1.65 (q,J=5.8 Hz, 2H), 1.57 (d,J=6.8 Hz, 4H).

[1133] MS(ESI, LR) Calculated for C 23 H 25 N4O2[M+H] + : 389.2, found: 389.1.

[1134] Example 139. 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one

[1135]

[1136] The target compound 139 was obtained by the synthetic method described in Example 132 using compound 138 and methyl iodide.

[1137] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.35 (d,J=8.4 Hz, 1H), 8.28 (s, 1H), 8.23 ​​(d,J=1.7 Hz, 1H), 8.01 (dd,J=8.4, 1.8 Hz, 1H), 7.94 (dd,J=8.9, 1.3 Hz, 1H), 7.56 (dd,J=8.9, 7.1 Hz, 2H), 7.30 (dd,J=7.0, 1.4 Hz, 1H), 6.72 (d,J=7.3 Hz, 1H), 3.63 (t, J=5.5 Hz, 4H), 3.56 (s, 3H), 1.66 (s, 2H), 1.57 (c, 4H).

[1138] MS(ESI, LR) Calculated for C 23 H 23 N4O2[M+H] + : 387.2, found: 387.1.

[1139] Example 141. 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1140]

[1141] The target compound 141 was obtained by the synthetic method described in Example 132 using compound 140 and methyl iodide.

[1142] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.28-8.22 (m, 2H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.91 (dd, J=8.9, 1.3 Hz, 1H), 7.77 (d, J=7.9 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.1, 1.4 Hz, 1H), 4.58 (s, 2H), 3.63 (t, J=5.4 Hz, 4H), 3.13 (s, 3H), 1.65 (d, J=8.0 Hz, 2H), 1.57 (s, 4H).

[1143] MS(ESI, LR) Calculated for C 22 H 23 N4O2[M+H] + : 375.2, found: 375.1.

[1144] Example 142. 2-isopropyl-6-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1145]

[1146] The target compound 142 was obtained by the synthetic method described in Example 132 using compound 140 and isopropyl iodide.

[1147] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.29-8.21 (m, 2H), 8.11 (dd, J=7.9, 1.7 Hz, 1H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.78 (d, J=7.9 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.25 (dd, J=7.1, 1.4 Hz, 1H), 4.56 (s, 2H), 4.47 (p, J=6.7 Hz, 1H), 3.63 (t, J=5.4 Hz, 4H), 1.72-1.63 (m, 2H), 1.57 (d, J=7.3 Hz, 4H), 1.28 (d, J=6.8 Hz, 6H).

[1148] MS(ESI, LR) Calculated for C 24 H 27 N4O2[M+H] + : 403.2, found: 403.1.

[1149] Example 144. 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1150]

[1151] The target compound 144 was obtained by the synthetic method described in Example 132 using compound 143 and methyl iodide.

[1152] 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.26 (s, 1H), 8.15 (s, 1H), 8.01 (dd,J=7.9, 1.6 Hz, 1H), 7.92 (dd,J=9.0, 1.3 Hz, 1.7,J=9.7), (d,J=9.3). Hz, 1H), 7.54 (dd,J=8.9, 7.0 Hz, 1H), 7.24 (dd,J=7.1, 1.4 Hz, 1H), 4.57 (s, 2H), 3.63 (t,J=5.4 Hz, 4H), 3.13 (s, 3H), (d,J=8.6,6.5). 2H), 1.57 (s, 4H).

[1153] MS(ESI, LR) Calculated for C 22 H 23 N4O2[M+H] + : 375.2, found: 375.1.

[1154] Example 259. [7-(3-amino-1,2-benzoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1155] <Scheme 33>

[1156]

[1157] Potassium tert-butyrate (64.4 mg, 0.57 mmol) and acetohydroxamic acid (43.1 mg, 0.57 mmol) were dissolved in N,N-dimethylformamide (3 mL) and stirred for 20 minutes. Compound 254 (100 mg, 0.29 mmol) was added and stirred for 1 hour, then the temperature was raised to 60°C and stirred for 1 hour. After completion of the reaction, the temperature of the reaction solution was lowered to room temperature, water was added, and it was filtered. The filtrate was separated using column chromatography to obtain the target compound 259 (36 mg, 33%).

[1158] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.41 (d, J=1.9 Hz, 1H), 8.26 (s, 1H), 8.06 (dd, J=8.8, 1.8 Hz, 1H), 7.90 (dd, J=8.9, 1.4 Hz, 1H), 7.62 (d, J=8.8 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.18 (dd, J=7.1, 1.4 Hz, 1H), 6.55 (s, 2H), 3.63 (t, J=5.5 Hz, 4H), 1.66 (d, J=5.6 Hz, 2H), 1.62-1.50 (m, 4H).

[1159] MS(ESI, LR) Calculated for C 20 H 20 N5O2[M+H] + : 362.2, found: 362.1.

[1160] Example 320. [7-(3-amino-1,2-benzoxazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1161]

[1162] Target compound 320 was obtained by the synthesis method described in Example 259 using compound 22.

[1163] 1 H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.26 (s, 1H), 8.04 (s, 1H), 7.98 (d,J=8.2 Hz, 1H), 7.92 (dd,J=8.9, 1.4 Hz, 1H, 7.7), ,J=8.8, Hz, 1H), 7.54 (dd,J=8.9, 7.0 Hz, 1H), 7.27 (dd,J=7.0, 1.4 Hz, 1H), 6.54 (s, 2H), 3.63 (t,J=5.4 Hz, 4H), 1.66 (s, 2H), (d,J=8.9, 7.7,7 4H).

[1164] MS(ESI, LR) Calculated for C 20 H 20 N5O2[M+H] + : 362.2, found: 362.1.

[1165] Example 260. [7-(3-amino-1H-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1166] <Scheme 34>

[1167]

[1168] Compound 254 (100 mg, 0.29 mmol) was dissolved in ethanol (3 mL), hydrazine hydrate (35.9 mg, 0.57 mmol) was added, and the mixture was stirred in a microwave reactor at 150°C for 35 minutes. The reaction solution was concentrated, diluted with water, and filtered. The filtrate was separated using column chromatography to obtain the target compound 260 (85 mg, 33%).

[1169] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 11.64 (s, 1H), 8.32-8.21 (m, 2H), 7.81 (ddd,J=20.3, 8.8, 1.5 Hz, 2H), 7.51 (dd,J=8.9, 7.0 Hz, 1H), 7.40-7.32 (m, 1H), 7.12 (dd,J=7.1, 1.4 Hz, 1H), 5.51 (s, 2H), 3.63 (t,J=5.4 Hz, 4H), 1.65 (d,J=5.3 Hz, 2H), 1.57 (s, 4H).

[1170] MS(ESI, LR) Calculated for C 20 H 21 N6O [M+H] + : 361.2, found: 361.1.

[1171] Example 309. [7-(3-amino-1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1172]

[1173] The target compound 309 was obtained by the synthetic method described in Example 260 using compound 22.

[1174] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 11.62 (s, 1H), 8.24 (d, J=1.1 Hz, 1H), 7.90-7.85 (m, 2H), 7.83 (d, J=8.4 Hz, 1H), 7.52 (dd, J=8.8, 7.1 Hz, 1H), 7.40-7.34 (m, 1H), 7.22 (dd, J=7.1, 1.4 Hz, 1H), 5.45 (s, 2H), 3.63 (t, J=5.3 Hz, 4H), 1.66 (d, J=6.9 Hz, 2H), 1.58 (d, J=7.3 Hz, 4H).

[1175] MS(ESI, LR) Calculated for C 20 H 21 N6O [M+H] + : 361.2, found: 361.1.

[1176] Example 261. [7-(3-amino-1-methyl-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1177] Example 310. [7-(3-amino-1-methyl-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1178] For Examples 261 and 310, compounds were prepared from compounds 254 and 22, respectively, using methylhydrazine and the same synthetic method as in Example 260. The structural and spectral data are shown in Table 27 below.

[1179] Table 27 Example Structure 1H NMR MS 261 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.37 (d, J=2.3 Hz, 1H), 8.25 (d, J=8.9 Hz, 2H), 7.88 (dd, J=8.8, 1.3 Hz, 1H), 7.51 (dd, J=8.9, 7.1 Hz, 1H), 7.43 (d, J=9.0 Hz, 1H), 7.24 (dd, J=7.1, 1.3 Hz, 1H), 4.32 (q, J=7.0 Hz, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.4 Hz, 2H), 1.57 (s, 4H), 1.43 (t, J=6.9 Hz, 3H). MS(ESI, LR) Calculated for C21H23N6O [M+H]+: 375.2, found: 375.1. 310 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.26 (s, 1H), 7.94 (d, J=8.9 Hz, 1H), 7.90 (d, J=8.1 Hz, 1H), 7.78 (d, J=1.5 Hz, 1H), 7.67-7.62 (m, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.31 (d, J=7.0 Hz, 1H), 4.29 (q, J=7.0 Hz, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.2 Hz, 2H), 1.57 (d, J=5.8 Hz, 4H), 1.41 (t, J=7.0 Hz, 3H). MS(ESI, LR) Calculated for C21H23N6O [M+H]+: 375.2, found: 375.1.

[1180] Example 395. (7-(1-((1,2,4-oxadiazol-3-yl)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1181] <Diagram 35>

[1182]

[1183] Step 395-1: Compound 1-2 and 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]acetonitrile and the synthetic method of Step 159-3 of Example 159 were used to obtain the target compound 395-1.

[1184] Step 395-2: The target compound 395-2 was prepared by the synthetic method of Step 115-1 of Example 115 using compound 395-1 and DIPEA.

[1185] Step 395-3: To compound 395-2 (100 mg, 0.27 mmol) were added trimethyl orthoformate (1.49 mL, 13.6 mmol) and trifluoroacetic acid (8.3 μL), and the mixture was stirred at 60°C for 1 hour. After completion of the reaction, the reaction solution was diluted with dichloromethane (10 mL) and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to obtain the target compound 395 (39 mg, 38%).

[1186] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.64 (s, 1H), 9.13 (s, 1H), 8.48 (s, 1H), 8.35 (s, 1H), 7.78 (dd,J=8.7, 1.4 Hz, 1H), 7.58 (dd,J=7.3, 1.4 Hz, 1H), 7.50 (dd,J=8.7, 7.2 Hz, 1H), 5.80 (s, 2H), 3.62 (t,J=5.4 Hz, 4H), 1.65 (d,J=5.5 Hz, 2H), 1.57 (d,J=5.6 Hz, 4H).

[1187] MS(ESI, LR) Calculated for C 19 H 20 N7O2[M+H] + : 378.2, found: 378.1.

[1188] Example 396. 3-((4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-1H-pyrazol-1-yl)methyl)-1,2,4-oxadiazol-5(4H)-one

[1189]

[1190] The target compound 396 was obtained by the synthetic method described in Example 349 using compound 395-5.

[1191] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.95 (s, 1H), 8.43 (s, 1H), 8.36 (s, 1H), 7.77 (d,J=8.8 Hz, 1H), 7.56 (t,J=6.3 Hz, 1H), 7.51-7.47 (m, 1H), 5.10 (s, 2H), 3.63 (t,J=5.5 Hz, 4H), 1.66 (s, 2H), 1.57 (s, 4H).

[1192] MS(ESI, LR) Calculated for C 19 H 20 N7O3[M+H] + : 394.2, found: 394.1.

[1193] Example 397. (7-(2-(1-((1,2,4-oxadiazol-3-yl)methyl)-1H-pyrazol-4-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1194] <Diagram 36>

[1195]

[1196] Step 397-1: The target compound 397-1 was obtained by the synthetic method of Step 159-3 of Example 159 using compound 1-2.

[1197] Step 397-2: The target compound 397-2 was obtained by the synthetic method of Step 395-1 of Example 395 using compound 397-1.

[1198] Step 397-3: The target compound 397-3 was obtained by the same method as in Step 395-2 of Example 395 using compound 397-2.

[1199] Step 397-4: The target compound 397 was obtained by the synthetic method of Step 395-3 of Example 395 using compound 397-3.

[1200] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.64 (s, 1H), 8.71 (d,J=5.2 Hz, 1H), 8.56 (s, 1H), 8.29 (s, 1H), 8.21 (s, 1H), 8.15 (s, 1H), 7.97 (dd,J=8.9, 1.4 Hz, 1H), 7.78 (dd,J=5.2, 1.6 Hz, 1H), 7.56 (dd,J=8.9, 7.0 Hz, 1H), 7.39 (dd,J=7.0, 1.4 Hz, 1H), 5.69 (s, 2H), 3.63 (t,J=5.4 Hz, 4H), 1.66 (d, J=5.6 Hz, 2H), 1.57 (d, J=6.7 Hz, 4H).

[1201] MS(ESI, LR) Calculated for C 24 H 23 N8O2[M+H]+ : 455.2, found: 455.1.

[1202] Example 146. 4-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)benzonitrile

[1203] <Diagram 37>

[1204]

[1205] Compound 1-2 (0.05 g, 0.14 mmol), palladium acetate (1.58 mg, 0.007 mmol), BINAP (8.7 mg, 0.01 mmol), and cesium carbonate (183.4 mg, 0.56 mmol) were dissolved in 1,4-dioxane (2 mL), and the mixture was stirred at 100 °C for 16 hours after filling with nitrogen gas. After completion of the reaction, the reaction solution was diluted with dichloromethane (10 mL) and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated using column chromatography to give the target compound 146 (16 mg, 32%). [BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)]

[1206] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.72 (s, 1H), 8.28 (s, 1H), 7.85-7.73 (m, 2H), 7.58-7.50 (m, 2H), 7.49-7.35 (m, 2H), 6.88 (dd, J=7.1, 1.5 Hz, 1H), 3.61 (t, J=5.4 Hz, 4H), 1.65 (d, J=5.4 Hz, 2H), 1.57 (d, J=7.3 Hz, 4H).

[1207] MS(ESI, LR) Calculated for C 20 H 20 N5O [M+H] + : 346.2, found: 346.1.

[1208] Example 147. 3-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)pyridin-2(1H)-one

[1209] Example 148. piperidin-1-yl(7-((pyrimidin-2-ylmethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone

[1210] Example 149. piperidin-1-yl(7-((2-(pyridin-4-yl)ethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone

[1211] Example 150. (7-((1-methylpiperidin-4-yl)amino)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1212] Example 211. 7-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-3,4-dihydro-2H-isoquinolin-1-one

[1213] Example 212. 6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]isoindolin-1-one

[1214] Example 238. [7-[(4-chlorophenyl)methylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1215] Example 242. [7-[2-(4-chlorophenyl)ethylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[1216] For Examples 147, 148, 149, 150, 211, 212, 238, and 242, compounds were prepared according to the synthetic method described in Example 146 using compound 1-2 and the corresponding compounds. The structural and spectral data are shown in Table 28 below.

[1217] Table 28 Example Structure 1H NMR MS 147 1H NMR (400 MHz, DMSO-d6) δ(ppm): 12.12 (s, 1H), 9.19 (s, 1H), 8.31 (s, 1H), 7.60 (dd, J=7.3, 1.6 Hz, 1H), 7.45 (t, J=8.2 Hz, 1H), 7.37 (dd, J=8.8, 1.1 Hz, 1H), 7.12 (dd, J=6.7, 1.6 Hz, 1H), 7.00-6.87 (m, 1H), 6.33 (t, J=6.9 Hz, 1H), 3.61 (t, J=5.3 Hz, 4H), 1.65 (d, J=7.8 Hz, 2H), 1.57 (d, J=6.8 Hz, 4H). MS(ESI, LR) Calculated for C18H20N5O2 [M+H]+: 338.2, found: 338.1. 148 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.84 (d, J=4.9 Hz, 2H), 8.23 ​​(s, 1H), 7.66 (t, J=5.7 Hz, 1H), 7.46 (t, J=4.9 Hz, 1H), 7.30 (t, J=8.1 Hz, 1H), 7.13-7.04 (m, 1H), 6.09 (d, J=7.6 Hz, 1H), 4.81 (d, J=5.7 Hz, 2H), 3.60 (t, J=5.4 Hz, 4H), 1.64 (d, J=5.8 Hz, 2H), 1.56 (sq., J=5.8 Hz, 4H). MS(ESI, LR) Calculated for C18H21N6O [M+H]+: 337.2, found: 337.1. 149 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.53-8.42 (m, 2H), 8.15 (s, 1H), 7.39-7.26 (m, 3H), 7.12 (t, J=6.1 Hz, 1H), 7.05 (dd, J=8.7, 1.1 Hz, 1H), 6.21 (d, J=7.6 Hz, 1H), 3.64 (sq., J=6.8 Hz, 2H), 3.57 (t, J=5.4 Hz, 4H), 3.01 (t, J=7.2 Hz, 2H), 1.63 (d, J=5.9 Hz, 2H), 1.54 (d, J=4.9 Hz, 4H). MS(ESI, LR) Calculated for C20H24N5O [M+H]+: 350.2, found: 350.1. 150 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.15 (s, 1H), 7.31 (t, J=8.2 Hz, 1H), 7.04 (dd, J=8.7, 1.1 Hz, 1H), 6.63 (d, J=8.5 Hz, 1H), 6.19 (d, J=7.7 Hz, 1H), 3.58 (t, J=5.4 Hz, 4H), 3.55-3.45 (m, 1H), 2.75 (d, J=11.2 Hz, 2H), 2.19 (s, 3H), 2.13-2.02 (m, 2H), 1.98-1.88 (m, 2H), 1.72 (td, J=10.9, 2.8 Hz, 2H), 1.64 (dt, J=11.0, 4.7 Hz, 2H), 1.54 (p, J=5.6 Hz, 4H). MS(ESI, LR) Calculated for C19H28N5O [M+H]+: 342.2, found: 342.2. 211 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.09 (d, J=1.5 Hz, 2H), 7.91 (s, 1H), 7.42 (dd, J=8.1, 2.5 Hz, 1H), 7.37 (dd, J=8.8, 1.2 Hz, 1H), 7.29-7.24 (m, 2H), 6.57 (dd, J=7.7, 1.2 Hz, 1H), 6.07 (s, 1H), 3.71 (t, J=5.3 Hz, 4H), 3.61 (td, J=6.6, 2.8 Hz, 2H), 3.02 (t, J=6.6 Hz, 2H), 1.78-1.64 (m, 6H). MS(ESI, LR) Calculated for C22H24N5O2 [M+H]+: 390.2, found: 390.1. 212 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.11 (s, 1H), 8.00 (s, 1H), 7.90 (d, J=1.6 Hz, 1H), 7.52 (d, J=1.4 Hz, 2H), 7.45-7.36 (m, 1H), 7.29 (d, J=8.0 Hz, 1H), 6.78 (s, 1H), 6.62 (d, J=7.5 Hz, 1H), 4.49 (s, 2H), 3.71 (t, J=5.3 Hz, 4H), 1.78-1.66 (m, 6H). MS(ESI, LR) Calculated for C21H22N5O2 [M+H]+: 376.2, found: 376.1. 238 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.20 (s, 1H), 7.90 (t, J=6.5 Hz, 1H), 7.47-7.35 (m, 4H), 7.23 (t, J=8.1 Hz, 1H), 7.03 (dd, J=8.7, 1.2 Hz, 1H), 5.95 (dd, J=7.7, 1.1 Hz, 1H), 4.59 (d, J=6.5 Hz, 2H), 3.58 (t, J=5.4 Hz, 4H), 1.64 (d, J=5.3 Hz, 2H), 1.54 (t, J=5.9 Hz, 4H). MS(ESI, LR) Calculated for C20H22ClN4O [M+H]+: 369.1, found: 369.1. 242 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.15 (s, 1H), 7.40-7.27 (m, 5H), 7.10-7.01 (m, 2H), 6.19 (dd, J=7.8, 1.2 Hz, 1H), 3.67-3.52 (m, 6H), 2.98 (t, J=7.3 Hz, 2H), 1.68-1.59 (m, 2H), 1.55 (qt, J=5.7 Hz, 4H). MS(ESI, LR) Calculated for C21H24ClN4O [M+H]+: 383.2, found: 383.1.

[1218] Example 194. (7-((3-methoxyphenyl)thio)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1219] <Diagram 38>

[1220]

[1221] Compound 1-2 (0.06 g, 0.17 mmol), tris(dibenzylideneacetone)dipalladium(0) (3.86 mg, 0.025 mmol), Xantphos (4.88 mg, 0.05 mmol), DIPEA (43.6 mg, 0.34 mmol) and 3-methoxybenzenethiol (71.05 mg, 0.51 mmol) were dissolved in 1,4-dioxane (2 mL), and the mixture was stirred at 100 °C for 1 hour after filling with nitrogen gas. After completion of the reaction, the reaction solution was diluted with dichloromethane (10 mL) and washed with water and saturated brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to give the target compound 194 (61 mg, 98%).

[1222] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.32 (s, 1H), 7.68 (dd,J=8.8, 1.2 Hz, 1H), 7.50 (t,J=8.2 Hz, 1H), 7.32 (dd,J=8.8, 7.4 Hz, 1H), 7.29-7.22 (m, 2H), 7.20-7.14 (m, 1H), 6.34 (dd,J=7.3, 1.2 Hz, 1H), 3.81 (s, 3H), 3.60 (t,J=5.4 Hz, 4H), 1.72-1.60 (m, 2H), 1.60-1.48 (m, 4H).

[1223] MS(ESI, LR) Calculated for C 20 H 22 N3O2S [M+H] + : 368.1, found: 368.1.

[1224] Example 235. 4-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-1H-pyrimidin-6-one

[1225]

[1226] The target compound 235 was obtained by the synthetic method described in Example 194 using compound 1-2, palladium acetate and corresponding compounds.

[1227] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 12.24 (s, 1H), 9.77 (s, 1H), 8.27 (s, 1H), 8.15 (s, 1H), 7.58-7.39 (m, 3H), 6.07 (s, 1H), 3.61 (t,J=5.4 Hz, 4H), 1.71-1.61 (m, 2H), 1.56 (d, J=7.9 Hz, 4H).

[1228] MS(ESI, LR) Calculated for C 17 H 19 N6O2[M+H] + : 339.1, found: 339.1.

[1229] Example 236. 3-methyl-6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]pyrimidin-4-one

[1230] <Scheme 39>

[1231]

[1232] Step 236-1: Compound 236-1 was prepared using compound 1-2 and diphenylmethanimine according to the synthetic method described in Example 146.

[1233] Step 236-2: Compound 236-1 (2 g, 4.89 mmol), hydroxyamine hydrochloride (0.68 g, 9.79 mmol), and sodium acetate (1 g, 12.24 mmol) were dissolved in methanol (48 mL) and stirred at room temperature for 16 hours. The reaction solution was concentrated, and the residue was separated using column chromatography to give the target compound 236-2 (845 mg, 69%).

[1234] Step 236-3: The target compound 236 was prepared according to the synthetic method described in Example 235 using compound 236-2 and 6-bromo-3-methyl-pyrimidin-4-one.

[1235] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 9.79 (s, 1H), 8.43 (s, 1H), 8.27 (s, 1H), 7.56-7.40 (m, 3H), 6.16 (s, 1H), 3.61 (t, J=5.4 Hz, 4H), 3.38 (s, 3H), 1.65 (sq, J=5.7 Hz, 2H), 1.57 (sq, J=5.8 Hz, 4H).

[1236] MS(ESI, LR) Calculated for C18 H 21 N6O2[M+H] + : 353.2, found: 353.1.

[1237] Example 239. 4-chloro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzamide

[1238] <Diagram 40>

[1239]

[1240] Compound 236-2 (70 mg, 0.28 mmol) was dissolved in pyridine (2.6 mL), dimethylaminopyridine (17.5 mg, 0.14 mmol) and 4-chlorobenzoyl chloride (75.2 mg) were added, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated, and the residue was separated using column chromatography to obtain the target compound 239 (60 mg, 53%).

[1241] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.25 (d,J=8.2 Hz, 1H), 8.11-8.04 (m, 1H), 7.91-7.86 (m, 1H), 7.84-7.77 (m, 2H), 7.66-7.61 (m, 1H), 7.46-7.39 (m, 2H), 3.81-3.69 (m, 4H), 1.82-1.74 (m, 2H), 1.69-1.67 (m, 4H).

[1242] MS(ESI, LR) Calculated for C 20 H 20 ClN4O2[M+H] +: 383.1, found: 383.1.

[1243] Example 240. 1,3,5-trimethyl-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrazole-4-sulfonamide

[1244] Example 241. 5-fluoro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-3-carboxamide

[1245] For Examples 240 and 241, compounds were prepared by the synthesis method described in Example 239 using compound 236-2 and corresponding compounds. The structural and spectral data are shown in Table 29 below.

[1246] Table 29 Example Structure 1H NMR MS 240 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.01 (s, 1H), 8.19 (s, 1H), 7.59 (d, J=8.8 Hz, 1H), 7.38 (dd, J=8.9, 7.4 Hz, 1H), 6.88 (d, J=7.4 Hz, 1H), 3.60 (s, 3H), 3.57 (t, J=5.4 Hz, 4H), 2.35 (s, 3H), 2.18 (s, 3H), 1.63 (d, J=6.5 Hz, 2H), 1.55 (sq, J=5.7 Hz, 4H). MS(ESI, LR) Calculated for C19H25N6O3S [M+H]+: 417.2, found: 417.1. 241 1H NMR (400 MHz, DMSO-d6) δ(ppm): 11.13 (s, 1H), 9.06 (t, J=1.7 Hz, 1H), 8.88 (d, J=2.8 Hz, 1H), 8.32 (s, 1H), 8.29 (ddd, J=9.3, 2.8, 1.7 Hz, 1H), 7.74 (dd, J=7.8, 2.4 Hz, 1H), 7.58-7.50 (m, 2H), 3.62 (t, J=5.4 Hz, 4H), 1.65 (q, J=5.8 Hz, 2H), 1.57 (p, J=5.6 Hz, 4H). MS(ESI, LR) Calculated for C19H19FN5O2 [M+H]+: 368.1, found: 368.1.

[1247] Example 151. 1-(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)pentan-1-one

[1248] <Diagram 41>

[1249]

[1250] Step 151-1: The target compound 151-1 was obtained in the same synthetic method as in Step 1-2 in Example 1 using pyrazolo[1,5-a]pyridine-3-carboxylic acid.

[1251] Step 151-2: Compound 151-1 (1 g, 4.36 mmol) was dissolved in tetrahydrofuran (15 mL), the temperature was lowered to -78°C, and lin-butyllithium (2.5 M solution, 2.44 mL, 6.1 mmol) was slowly added. After the reaction solution was stirred for 30 min, 1,2-iodoethane (1.47 g, 5.23 mmol) dissolved in tetrahydrofuran (9 mL) was added. After the reaction solution was stirred for 3 h, the temperature was slowly raised to room temperature, and the mixture was diluted with saturated aqueous sodium bicarbonate solution (20 mL) and dichloromethane (20 mL). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated using column chromatography to give the title compound 151-2 (151 mg, 11%).

[1252] Step 151-3: Using compound 151-2, the target compound 151 was obtained in the same synthetic method as in Steps 1 to 3 in Example 1.

[1253] 1H NMR (400 MHz, DMSO-d6) δ(ppm): 9.35 (d,J=2.2 Hz, 1H), 8.78 (d,J=2.2 Hz, 1H), 8.54 (dd,J=8.8, 1.4 Hz, 1H), 8.41 (s, 1H), 8.20 (d,J=8.5 Hz, 1H), 7.95 (d,J=8.1 Hz, 1H), 7.82 (dd,J=8.4, 6.9, 1.5 Hz, 1H), 7.70-7.56 (m, 2H), 7.23 (dd,J=7.1, 1.4 Hz, 1H), 2.93 (t,J=7.5 Hz, 2H), 1.79 (p,J=7.6 Hz, 2H), 1.46 (h, J=7.4 Hz, 2H), 0.98 (t, J=7.3 Hz, 3H).

[1254] MS(ESI, LR) Calculated for C 21 H 20 N3O [M+H] + : 330.2, found: 330.2.

[1255] Example 152. 4-(3-acetylpyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[1256] <Scheme 42>

[1257]

[1258] Step 152-1: The target compound 152-1 was obtained in the same synthetic method as in Step 1-3 in Example 1 using pyrazolo[1,5-a]pyridine-3-carboxylic acid and 4-cyanophenylboronic acid.

[1259] Step 152-2: The target compound 152-2 was obtained in the same synthetic method as in Step 1-2 in Example 1 using compound 152-1 and dimethylhydroxylamine.

[1260] Step 152-3: Compound 152-2 (0.05 mg, 0.16 mmol) was dissolved in tetrahydrofuran (2 mL), the temperature was lowered to 0 °C, and methyl magnesium bromide (3 M solution, 0.1 mL, 0.33 mmol) was slowly added. The reaction solution was stirred for 3 hours, diluted with saturated aqueous ammonium chloride solution (10 mL) and ethyl acetate (10 mL). The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated using column chromatography to give the target compound 152 (11 mg, 24%).

[1261] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.72 (s, 1H), 8.36 (dd, J=8.8, 1.3 Hz, 1H), 8.14 (d, J=8.3 Hz, 2H), 8.05 (d, J=8.4 Hz, 2H), 7.76 (dd, J=8.8, 7.2 Hz, 1H), 7.43 (dd, J=7.2, 1.4 Hz, 1H), 2.54 (s, 3H).

[1262] MS(ESI, LR) Calculated for C 16 H 12 N3O [M+H] + : 262.1, found: 262.1.

[1263] Example 153. 4-(3-(2-hydroxypropan-2-yl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[1264] <Scheme 43>

[1265]

[1266] The target compound 153 was obtained in the same synthetic method as in Step 152-3 in Example 152 using compound 152-2.

[1267] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.72 (s, 1H), 8.35 (dd, J=8.8, 1.3 Hz, 1H), 8.17-8.11 (m, 2H), 8.08 (d, J=8.5 Hz, 2H), 7.76 (dd,J=8.8, 7.1 Hz, 1H), 7.41 (dd,J=7.2, 1.4 Hz, 1H), 2.67 (s, 3H), 2.55 (s, 3H).

[1268] MS(ESI, LR) Calculated for C 17 H 15 N2O2[M+H] + : 279.1, found: 279.1.

[1269] Example 154. 7-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1270] <Scheme 44>

[1271]

[1272] Step 154-1: The target compound 154-1 was obtained in the same synthetic method as in Step 1-2 in Example 1 using compound 1-1 and 4-fluoropiperidine.

[1273] Step 154-2: The target compound 154 was obtained in the same synthetic method as in Step 1-3 in Example 1, using compound 154-1 and 7-(4,4,5,5,-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-isoquinolin-1-one.

[1274] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.41 (d, J=2.0 Hz, 1H), 8.30 (s, 1H), 8.07 (s, 1H), 8.01 (dd, J=7.9, 2.0 Hz, 1H), 7.92 (dd, J=8.9, 1.3 Hz, 1H), 7.57-7.48 (m, 2H), 7.21 (dd, J=7.1, 1.4 Hz, 1H), 3.80-3.62 (m, 4H), 3.45 (td, J=6.6, 2.7 Hz, 2H), 3.02 (t, J=6.5 Hz, 2H), 2.06-1.82 (m, 3H), 1.82-1.67 (m, 2H).

[1275] MS(ESI, LR) Calculated for C 22 H 22 FN4O2[M+H] + : 393.2, found: 393.1.

[1276] Example 155. 6-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1277] Example 156. 4-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[1278] Example 157. (4-fluoropiperidin-1-yl)(7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[1279] Example 231. 6-(3-(4-fluoropiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methylisoindolin-1-one

[1280] For Examples 155, 156, 157, and 231, compounds were prepared in the same synthetic method as in Step 1-3 of Example 1, using compound 154-1 and the corresponding compounds. The structural and spectral data are shown in Table 30 below.

[1281] Table 30 Example Structure 1H NMR MS 155 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.31 (s, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.93 (dd, J=8.8, 1.4 Hz, 1H), 7.77 (d, J=7.9 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.27 (dd, J=7.1, 1.4 Hz, 1H), 4.50 (s, 2H), 3.81-3.62 (m, 4H), 2.06-1.81 (m, 3H), 1.78 (d, J=3.5 Hz, 2H). MS(ESI, LR) Calculated for C21H20FN4O2 [M+H]+: 379.2, found: 379.1. 156 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.31 (s, 1H), 8.18-8.12 (m, 2H), 8.07-8.01 (m, 2H), 7.96 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.30 (dd, J=7.0, 1.3 Hz, 1H), 3.80-3.60 (m, 4H), 2.12-1.82 (m, 3H), 1.77 (td, J=6.8, 3.5 Hz, 2H). MS(ESI, LR) Calculated for C20H17FN4O [M+H]+: 349.1, found: 349.1. 157 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.43-8.38 (m, 2H), 8.33 (s, 1H), 8.27-8.23 (m, 2H), 7.99 (dd, J=8.9, 1.3 Hz, 1.3 Hz, 7.9, J=8.9, dd 7.1 Hz, 1H), 7.34 (dd, J=7.1, 1.4 Hz, 1H), 3.81-3.61 (m, 4H), 2.15-1.60 (m, 5H). MS(ESI, LR) Calculated for C19H18FN4O3 [M+H]+: 369.1, found: 369.0. 231 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.31 (s, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.93 (dd, J=7.9, 1.7 Hz, 7.7 Hz), (d, J=7.9 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.3 Hz, 1H), 5.05-4.85 (m, 1H), 4.58 (s, 2H), 3.8-3, 3.3H), (3.3H), (s, 3H), 2.04-1.71 (m, 5H). MS(ESI, LR) Calculated for C22H22FN4O2 [M+H]+: 393.2, found: 393.1.

[1282] Example 158. Cyclohexyl(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[1283] <Diagram 45>

[1284]

[1285] Step 158-1: The target compound 158-1 was obtained in the same synthetic method as in Step 1-3 in Example 1 using pyrazolo[1,5-a]pyridine-3-carboxylic acid and phenylboronic acid.

[1286] Step 158-2: The target compound 158-2 was obtained in the same synthetic method as in Step 1-2 in Example 1 using compound 158-1 and dimethylhydroxylamine.

[1287] Step 158-3: The target compound 158 was obtained in the same synthetic method as in Step 152-3 in Example 152 using compound 158-2 and cyclohexylmagnesium bromide.

[1288] 1 H NMR (400 MHz, DMSO-d6) δ(ppm): 8.75 (s, 1H), 8.33 (dd,J=8.8, 1.4 Hz, 1H), 7.97-7.86 (m, 2H), 7.72 (dd,J=8.8, 7.2 Hz, 1H), 7.57 (dd,J=5.2, 2.0 Hz, 3H), 7.31 (dd,J=7.1, 1.4 Hz, 1H), 3.23 (s, 1H), 1.91-1.64 (m, 5H), 1.53-1.35 (m, 4H), 1.22 (d, J=11.4 Hz, 1H).

[1289] MS(ESI, LR) Calculated for C 20 H 21 N2O [M+H] + : 305.2, found: 305.1.

[1290] Example 227. (2-azabicyclo[2,2,1]heptan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[1291] Example 228. (2-azabicyclo[2,2,2]octan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[1292] Example 229. (7-azabicyclo[2,2,1]heptan-7-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[1293] For Examples 227, 228, and 229, compounds were prepared in the same synthetic manner as in Step 1-2 of Example 1, using compound 158-1 and the corresponding compounds. The structural and spectral data are shown in Table 31 below.

[1294] Table 31 Example Structure 1H NMR MS 227 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.42-8.25 (m, 2H), 7.91 (s, 2H), 7.59-7.49 (m, 4H), 7.19 (dd, J=7.1, 1.5 Hz, 4.20, J=7.8), J Hz, 1H), 3.80 (s, 1H), 3.44 (dd, J=37.2, 9.6 Hz, 1H), 2.65 (s, 1H), 1.87-1.61 (m, 4H), 1.46 (d, J=10.2 Hz, 2H). MS(ESI, LR) Calculated for C20H20N3O [M+H]+: 318.2, found: 318.1. 228 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.28-8.12 (m, 1H), 7.91 (dd, J=7.4, 2.3 Hz, 3H), 7.60-7.45 (m, 4H), 7.17 (s, 1H), 4.29 (d, J=143.2 Hz, 1H), 3.80 (s, 1H), 3.50 (s, 1H), 1.96 (d, J=40.8 Hz, 3H), 1.67 (s, 6H). MS(ESI, LR) Calculated for C21H22N3O [M+H]+: 332.2, found: 332.1. 229 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.41 (s, 1H), 8.02 (dd, J=8.9, 1.4 Hz, 1H), 7.94-7.89 (m, 2H), 7.60-7.52 (m, 4H), 7.19 (dd, J=7.1, 1.4 Hz, 1H), 4.53-4.45 (m, 2H), 1.85-1.74 (m, 4H), 1.50 (d, J=7.1 Hz, 4H). MS(ESI, LR) Calculated for C20H20N3O [M+H]+: 318.2, found: 318.1.

[1295] Example 234. 6-(3-(4,4-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1296] Example 378. 6-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1297] Example 382. 6-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1298] Example 385. (R)-6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1299] Example 386. (S)-6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1300] Example 387. 6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1301] Example 390. 6-(3-(2-azaspiro[3,3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1302] Example 391. 6-(3-(6-azaspiro[3,4]octane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1303] Example 392. 6-(3-(7-azaspiro[3,5]nonane-7-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1304] Example 393. 6-(3-(3-ethylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1305] Example 398. 6-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1306] Example 400. 6-(3-(3-isopropylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1307] Example 401. 6-(3-(1,2,3,6-tetrahydropyridine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1308] Example 405. 6-(3-(6-azaspiro[3,5]nonane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1309] Example 411. 6-(3-(6-fluoro-2-azaspiro[3,3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1310] Example 412. 6-(3-(6,6-difluoro-2-azaspiro[3,3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1311] For Examples 234, 378, 382, ​​385, 386, 387, 390, 391, 392, 393, 398, 400, 401, 405, 411 and 412, intermediate compounds were obtained in the same synthetic method as in Step 1-2 in Example 1 using compound 1-1 and the corresponding compounds, and then the compounds were obtained in the same synthetic method as in Step 1-3 in Example 1 using 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one. The structural and spectral data are shown in Table 32 below.

[1312] Table 32 Example Structure 1H NMR MS 234 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.70 (s, 1H), 8.35 (s, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.12 (dd, J=8.0, 1.7 Hz, 1H), 7.96 (dd, J=8.9, 1.4 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.56 (dd, J=8.9, 7.0 Hz, 1H), 7.29 (dd, J=7.0, 1.3 Hz, 1H), 4.50 (s, 2H), 3.78 (t, J=5.9 Hz, 4H), 2.15-2.03 (m, 4H). MS(ESI, LR) Calculated for C21H19F2N4O2 [M+H]+: 397.1, found: 397.0. 378 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.71 (s, 1H), 8.31-8.19 (m, 2H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.91 (dd, J=7.9, 1.7 Hz, 7.7 Hz), J=7.9 Hz, 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.27 (dd, J=7.1, 1.3 Hz, 1H), 4.81 (d, J=47.4 Hz, 1H), 4.14-3.92 (m, 3.2 Hz), (m, 7.2H), (m 2.00-1.84 (m, 2H), 1.80 (m, 1H), 1.64-1.49 (m, 1H). MS(ESI, LR) Calculated for C21H20FN4O2 [M+H]+: 379.1, found: 379.0. 382 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.71 (s, 1H), 8.31 (s, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.13 (dd, J=7.9, 1.7 Hz, 1.9H), J, 7.2, 18.9, 1H Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.58 (dd, J=8.9, 7.1 Hz, 1H), 7.30 (dd, J=7.1, 1.3 Hz, 1H), 4.50 (s, 2H), 4.00 (t, J=1,2,2H), J=5.5 Hz, 2H), 2.13 (m, 2H), 1.78 (m, 2H). MS(ESI, LR) Calculated for C21H19F2N4O2 [M+H]+: 397.1, found: 397.1. 385 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.25 (s, 2H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.77 (d, J=7.9 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 4.50 (s, 2H), 4.19 (m, 2H), 3.00 (m, 1H), 2.69 (m, 1H), 1.82 (m, 1H), 1.67 (m, 2H), 1.48 (m, 1H), 1.20 (m, 1H), 0.89 (d, J=6.6 Hz, 3H). MS(ESI, LR) Calculated for C22H23N4O2 [M+H]+: 375.2, found: 375.1. 386 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.25 (s, 1H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.90 (dd, J=8.9, 1.3 Hz, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 4.50 (s, 2H), 4.18 (m, 2H), 3.00 (m, 1H), 2.68 (m, 1H), 1.82 (m, 1H), 1.70 (m, 2H), 1.46 (m, 1H), 1.20 (m, 1H), 0.89 (d, J=6.6 Hz, 3H). MS(ESI, LR) Calculated for C22H23N4O2 [M+H]+: 375.2, found: 375.1. 387 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.25 (s, 2H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.91 (dd, J=8.9, 1.3 Hz, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 4.50 (s, 2H), 4.18 (s, 2H), 3.00 (s, 1H), 2.69 (s, 1H), 1.82 (d, J=12.7 Hz, 1H), 1.67 (dd, J=27.1, 10.3 Hz, 2H), 1.48 (q, J=12.1 Hz, 1H), 1.26-1.11 (m, 1H), 0.89 (d, J=6.5 Hz, 3H). MS(ESI, LR) Calculated for C22H23N4O2 [M+H]+: 375.2, found: 375.1. 390 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.33 (s, 1H), 8.29 (dd, J=8.9, 1.4 Hz, 1H), 8.23 ​​(d, J=1.6 Hz, 1H), 8.11 (dd, J=8.0, 1.7 Hz, 1H), 7.77 (d, J=7.9 Hz, 1H), 7.59 (dd, J=8.9, 7.1 Hz, 1H), 7.31 (dd, J=7.1, 1.4 Hz, 1H), 4.50 (s, 2H), 4.44 (m, 2H), 4.04 (m, 2H), 2.20 (t, J=7.6 Hz, 4H), 1.82 (m, 2H). MS(ESI, LR) Calculated for C22H21N4O2 [M+H]+: 373.2, found: 373.1. 391 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.71 (s, 1H), 8.47 (s, 1H), 8.26 (d, J=8.8 Hz, 2H), 8.14-8.07 (m, 1H), 7.77 (d, J, 7.0.7 H), 7.77 G (dd, J=8.9, 7.0 Hz, 1H), 7.30 (dd, J=7.2, 1.4 Hz, 1H), 4.50 (s, 2H), 3.78 (m, 2H), 3.53 (m, 2H), 1.96 (m, 8H). MS(ESI, LR) Calculated for C23H23N4O2 [M+H]+: 387.22, found: 387.1. 392 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.71 (s, 1H), 8.31-8.15 (m, 2H), 8.12 (dd, J=8.0, 1.7 Hz, 1H), 7.90 (dd, J=8.9, 1.4 Hz, 7.6 Hz), J=8.0 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.26 (dd, J=7.1, 1.3 Hz, 1H), 4.50 (s, 2H), 3.63-3.49 (m, 4H), 1.89 (m, 2H), (m, 4H), 1.65-1.48 (m, 4H). MS(ESI, LR) Calculated for C24H25N4O2 [M+H]+: 401.2, found: 401.1. 393 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.25 (s, 1H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.91 (dd, J=8.9, 1.4 Hz, 1H), 7.76 (d, J=8.0 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 4.49 (s, 2H), 4.22 (m, 2H), 3.03 (m, 1H), 2.70 (m, 1H), 1.88 (m, 1H), 1.71 (m, 1H), 1.46 (m, 2H), 1.23 (m, 3H), 0.88 (t, J=7.4 Hz, 3H). MS(ESI, LR) Calculated for C23H25N4O2 [M+H]+: 389.2, found: 389.1. 398 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.30 (s, 1H), 8.24 (d, J=1.6 Hz, 1H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.93 (dd, J=8.9, 1.3 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.56 (dd, J=8.9, 7.1 Hz, 1H), 7.28 (dd, J=7.1, 1.4 Hz, 1H), 4.50 (m, 3H), 4.18 (m, 1H), 3.11 (d, J=15.6 Hz, 2H), 2.67 (m, 1H), 2.02 (m, 1H), 1.79 (m, 1H), 1.69-1.48 (m, 2H). MS(ESI, LR) Calculated for C22H20F3N4O2 [M+H]+: 429.1, found: 429.1. 400 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.25 (d, J=1.9 Hz, 2H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.91 (dd, J=8.9, 1.3 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.26 (dd, J=7.0, 1.4 Hz, 1H), 4.50 (s, 2H), 4.28 (m, 2H), 2.96 (m, 1H), 2.72 (m, 1H), 1.86 (m, 1H), 1.73 (m, 1H), 1.45 (m, 2H), 1.37-1.16 (m, 2H), 0.89 (t, J=6.1 Hz, 6H). MS(ESI, LR) Calculated for C24H27N4O2 [M+H]+: 403.2, found: 403.1. 401 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.71 (s, 1H), 8.33 (s, 1H), 8.25 (d, J=1.7 Hz, 1H), 8.12 (dd, J=7.9, 1.7 Hz, 1H), 7.97 (dd, J=9.0, 1.4 Hz, 1H), 7.77 (d, J=8.0 Hz, 1H), 7.55 (dd, J=8.9, 7.0 Hz, 1H), 7.28 (dd, J=7.1, 1.4 Hz, 1H), 5.89 (d, J=10.1 Hz, 1H), 5.75 (d, J=9.6 Hz, 1H), 4.19 (s, 2H), 3.75 (t, J=5.7 Hz, 2H), 2.24 (s, 2H). MS(ESI, LR) Calculated for C21H19N4O2 [M+H]+: 359.1, found: 359.1. 405 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.71 (s, 1H), 8.26 (m, 2H), 8.13 (dd, J=7.9, 1.7 Hz, 1H), 7.89 (dd, J=8.9, 1.4 Hz, 1.7.7, J=7.8), J Hz, 1H), 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.0, 1.4 Hz, 1H), 4.50 (s, 2H), 3.62 (s, 2H), 3.57 (t, J=5.6 Hz, 2H), 17.2H), (17.2H), 1.70-1.62 (m, 4H), 1.58-1.45 (m, 2H). MS(ESI, LR) Calculated for C24H25N4O2 [M+H]+: 401.2, found: 401.1. 411 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 8.71 (s, 1H), 8.34-8.26 (m, 2H), 8.22 (d, J=1.7 Hz, 1H), 8.10 (dd, J=7.9 Hz, 1.7 Hz, 17.7, J=7.9), J Hz, 1H), 7.60 (dd, J=8.9, 7.1 Hz, 1H), 7.31 (dd, J=7.1, 1.4 Hz, 1H), 5.13-4.89 (m, 1H), 4.50 (m, 2H), 4.08 (m, 2H), v. J=8.6, k. 2H), 2.39 (ddd, J=20.1, 11.4, 7.9 Hz, 2H). MS(ESI, LR) Calculated for C22H20FN4O2 [M+H]+: 391.1, found: 391.1. 412 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.72 (s, 1H), 8.35-8.25 (m, 2H), 8.23 ​​(d, J=1.7 Hz, 1H), 8.10 (dd, J=8.0, 1.7 Hz, 1H), 7.77 (d, J=7.9 Hz, 1H), 7.61 (dd, J=8.9, 7.1 Hz, 1H), 7.32 (dd, J=7.1, 1.4 Hz, 1H), 4.59 (s, 1H), 4.50 (s, 2H), 4.18 (s, 1H), 2.89 (t, J=12.5 Hz, 4H). MS(ESI, LR) Calculated for C22H19F2N4O2 [M+H]+: 409.1, found: 409.1.

[1313] Example 336. (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methylpiperidin-1-yl)methanone

[1314] Example 337. (3-ethylpiperidin-1-yl)(7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[1315] Example 338. (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-(trifluoromethyl)piperidin-1-yl)methanone

[1316] For Examples 336, 337, and 338, intermediate compounds were obtained in the same synthetic method as in Step 1-2 of Example 1 using compound 1-1 and the corresponding compound, and then the compounds were obtained in the same synthetic method as in Step 1-3 of Example 1 using (6-fluoro-3-pyridyl)boronic acid. The structural and spectral data are shown in Table 33 below.

[1317] Table 33 Example Structure 1H NMR MS 336 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.78 (d, J=2.5 Hz, 1H), 8.61 (td, J=8.2, 2.5 Hz, 1H), 8.25 (s, 1H), 7.93 (dd, J=8.9, 1.4 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.41 (dd, J=8.6, 2.8 Hz, 1H), 7.30 (dd, J=7.1, 1.4 Hz, 1H), 4.16 (m, 2H), 3.00 (m, 1H), 2.69 (m, 1H), 1.82 (d, J=12.7 Hz, 1H), 1.75-1.55 (m, 2H), 1.47 (sq., J=12.2 Hz, 1H), 1.25-1.10 (m, 1H), 0.88 (d, J=6.6 Hz, 3H). MS(ESI, LR) Calculated for C19H20FN4O [M+H]+: 339.2, found: 339.1. 337 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.78 (d, J=2.5 Hz, 1H), 8.61 (td, J=8.2, 2.6 Hz, 1H), 8.25 (s, 1H), 7.93 (dd, J=8.9, 1.3 Hz, 1H), 7.54 (dd, J=8.9, 7.0 Hz, 1H), 7.41 (dd, J=8.6, 2.8 Hz, 1H), 7.30 (dd, J=7.1, 1.3 Hz, 1H), 4.20 (m, 2H), 3.03 (m, 1H), 2.72 (m, 1H), 1.88 (d, J=12.9 Hz, 1H), 1.71 (d, J=13.1 Hz, 1H), 1.57-1.36 (m, 2H), 1.23 (dq, J=19.1, 9.6 Hz, 3H), 0.88 (t, J=7.5 Hz, 3H). MS(ESI, LR) Calculated for C20H22FN4O [M+H]+: 353.2, found: 353.1. 338 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.78 (d, J=2.5 Hz, 1H), 8.61 (td, J=8.2, 2.5 Hz, 1H), 8.30 (s, 1H), 7.96 (dd, J=8.9, 1.4 Hz, 1H), 7.57 (dd, J=8.9, 7.1 Hz, 1H), 7.41 (dd, J=8.6, 2.8 Hz, 1H), 7.32 (dd, J=7.0, 1.3 Hz, 1H), 4.45 (d, J=13.0 Hz, 1H), 4.17 (d, J=13.3 Hz, 1H), 3.13 (dt, J=23.3, 12.0 Hz, 2H), 2.67 (s, 1H), 2.07-1.96 (m, 1H), 1.79 (d, J=12.3 Hz, 1H), 1.69-1.50 (m, 2H). MS(ESI, LR) Calculated for C19H17F4N4O [M+H]+: 393.1, found: 393.1.

[1318] Example 339. 3-(5-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1319] Example 353. 3-(5-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1320] Example 354. 3-(5-(3-(3-ethylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1321] Example 383. 3-(5-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1322] Example 384. 3-(5-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1323] For Examples 339, 353, 354, 383 and 384, intermediate compounds were obtained in the same synthetic method as in Step 1-2 in Example 1 using compound 1-1 and the corresponding compounds, and then the compounds were obtained in the same synthetic method as in Example 316. The structural and spectral data are shown in Table 34 below.

[1324] Table 34 Example Structure 1H NMR MS 339 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.93 (d, J=2.3 Hz, 1H), 8.46 (dd, J=8.9, 2.4 Hz, 1H), 8.30 (s, 1H), 8.26 (d, J=8.7 Hz, 1H), 7.93 (dd, J=8.9, 1.3 Hz, 1H), 7.56 (dd, J=8.9, 7.1 Hz, 1H), 7.30 (dd, J=7.1, 1.4 Hz, 1H), 4.52 (dd, J=8.7, 7.3 Hz, 2H), 4.45 (d, J=13.1 Hz, 1H), 4.27 (dd, J=8.8, 7.3 Hz, 2H), 4.17 (d, J=12.8 Hz, 1H), 3.11 (dd, J=22.1, 10.8 Hz, 2H), 2.67 (s, 1H), 2.02 (d, J=12.2 Hz, 1H), 1.79 (d, J=12.1 Hz, 1H), 1.68-1.48 (m, 2H). MS(ESI, LR) Calculated for C20H21F3N5O3 [M+H]+: 460.2, found: 460.1. 353 1H NMR (400 MHz, DMSO-d6) δ(ppm): 8.99-8.87 (m, 1H), 8.46 (dd, J=8.9, 2.4 Hz, 1H), 8.31-8.23 (m, 2H), 7.90 (dd, J=8.9, 1.3 Hz, 1H), 7.53 (dd, J=8.9, 7.1 Hz, 1H), 7.27 (dd, J=7.0, 1.4 Hz, 1H), 4.52 (t, J=8.0 Hz, 2H), 4.27 (dd, J=8.8, 7.3 Hz, 2H), 4.17 (m, 2H), 3.01 (m, 1H), 2.69 (m, 1H), 1.82 (d, J=13.1 Hz, 1H), 1.74-1.56 (m, 2H), 1.48 (sq., J=12.4 Hz, 1H), 1.29-1.14 (m, 1H), 0.89 (d, J=6.6 Hz, 3H). MS(ESI, LR) Calculated for C22H24N5O3 [M+H]+: 406.2, found: 406.1. 354 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 9.03-8.78 (m, 1H), 8.46 (dd, J=8.9, 2.4 Hz, 1H), 8.26 (d, J=8.2 Hz, 2H), 7.90 (dd, J=8.2 Hz, 2H), 7.90 (dd, J=8.2 Hz, 1.3, G 7.53 (dd, J=8.9, 7.0 Hz, 1H), 7.27 (dd, J=7.1, 1.3 Hz, 1H), 4.52 (dd, J=8.7, 7.3 Hz, 2H), 4.27 (dd, J=8.8, 7.3 Hz, 2H), (m (m, 1H), 2.73 (m, 1H), 1.88 (d, J=12.6 Hz, 1H), 1.71 (d, J=13.2 Hz, 1H), 1.52-1.38 (m, 2H), 1.35-1.12 (m, 3H), t 0, 7.7Hz (J=1.3H). MS(ESI, LR) Calculated for C23H26N5O3 [M+H]+: 406.2, found: 406.1. 383 1H NMR (400 MHz, DMSO-d6) δ(m.d.): 9.00-8.86 (m, 1H), 8.46 (dd, J=8.8, 2.5 Hz, 1H), 8.26 (d, J=10.2 Hz, 1H), 7.91, Jdd, J=10.2 Hz, 1H 1H), 7.55 (dd, J=8.9, 7.1 Hz, 1H), 7.47 (s, 2H), 7.34-7.25 (m, 1H), 4.81 (d, J=47.1 Hz, 2H), 4.52 (t, J=8.0 Hz, 2H), 4.52 (t, J=8.0 Hz, 2H), 3.76-3.61 (m, 1H), 3.57 (dd, J=15.3, 7.1 Hz, 1H), 1.9...

Claims

1. A heterocyclic compound represented by the following Formula 1, or a pharmaceutically acceptable salt thereof: , where the fused bicyclic ring is formed from ring A and ring B, X1, Y1, Y2, Y3 and Y4 independently represent CH or N, X2 is CH, N or NH, Z1 and Z2 represent C or N, at least one of X1, X2, Y1, Y2, Y3, Y4, Z1 and Z2 is N or NH, R a represents H, C 1-6 straight or branched chain alkyl substituted with R a-1 , or C(O)R a-1 , R a-1 represents C 1-6 straight or branched chain alkyl, C 3-8 cycloalkyl, hydroxy, R s or R u and R a-1 optionally substituted by one or more independent R a-2 , R a-2 represents C 1-6straight or branched chain alkyl, halogen, C 1-4 haloalkyl, X1 is optionally substituted with R b , where R b is amino or C(O)R s , Y1 is optionally substituted with R 1 , R 1 represents R f , Y2 is optionally substituted with R 2 , R 2 represents C 1-6 straight or branched chain alkyl, halogen, C 5-12 aryl with 1-2 rings, R u or R f and R 2 optionally substituted by one or more independent R 2-1 , R 2-1 represents C 1-4 alkoxy, halogen or hydroxy, Y3 is optionally substituted with R 3 , R 3 represents C 5-7 aryl, R u or R f and R 3 optionally substituted by one or more independent R 3-1 , R 3-1 represents C 1-4alkoxy, halogen, hydroxy or cyano, Y4 is optionally substituted with R 4 or -LR 4 , L is -NH(CH2) m -, -NHC(O)-, -NHSO2- or -S-, m is an integer from 0 to 3, R 4 represents C 5-12 aryl with 1-2 rings, R u , R s or R f and R 4 optionally substituted by one or more independent Q, Q represents C 1-6 straight or branched chain alkyl, halogen, hydroxy, C 1-4 haloalkyl, C 1-4 alkoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR 5 , CH2R 5 , NR 5 R 6 , C(O)R 5 , C(O)OR 5 , C(O)NR 5 R 6 , NHC(O)(CH2) p R 5 , NHC(O)CH2OR 5 , NHC(O)CH2NR 5 R 6 , NHCH2CH2R 5 , NR 5 C(O)R 6 , R u or R s, p is an integer from 0 to 3 and Q is optionally substituted by one or more independent R 7 , R 5 and R 6 independently represent H, C 1-6 straight or branched chain alkyl, C 3-8 cycloalkyl, C 1-4 alkoxy, amino, sulfonyl, C 5-7 aryl, arylalkyl, R u or R s , R 7 represents C 1-6 straight or branched chain alkyl, C 3-8 cycloalkyl, halogen, C 1-4 haloalkyl, hydroxy, C 1-4 alkoxy, hydroxyalkyl, cyano, amino, alkylamino, C 1-6 alkyl carboxylate, nitro, R u , WITH 1-4 alkyl substituted with R u , or R s , and the relationship between Q and R 7 represents a single bond or a double bond, R s is a 4- to 10-membered saturated heterocycloalkyl ring with 1-2 rings having from 1 to 3 heteroatoms selected from N, O and S, R u is a 5- to 7-membered unsaturated heterocycloalkyl ring having from 1 to 4 heteroatoms selected from N, O and S, R f is a fused bicyclic ring in which a 5- to 7-membered saturated or unsaturated heterocycloalkyl ring having 1-2 heteroatoms selected from N, O and S is fused with an aryl ring or a 5- to 7-membered heteroaryl ring having 1-2 N atoms, R s , R u and R f independently optionally substituted with one or two oxo (O) or thioxo (S) groups, except in cases where R a represents H and X1, Y1, Y2, Y3 and Y4 are all unsubstituted.

2. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein ring A is pyrrole, pyrazole, imidazole or triazole.

3. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein ring B is benzene, pyridine, pyrimidine or triazine.

4. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein the fused bicyclic ring consisting of ring A and ring B is indole, indazole, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, pyrazolopyridine, imidazopyridine or triazolopyridine.

5. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein the fused bicyclic ring consisting of ring A and ring B is a ring selected from the group consisting of the following:

6. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein R a represents H, propyl, C(O)R a-1 , R a-1is methyl, butyl, cyclohexyl, hydroxy, piperidinyl, azaspiroheptanyl, azaspirooctanyl, azaspirononanyl, azabicycloheptanyl, azabicyclooctanyl, azabicyclononanyl or tetrahydropyridinyl and R a-2 represents methyl, ethyl, propyl, isopropyl, fluorine, or trifluoromethyl.

7. A compound or a pharmaceutically acceptable salt thereof according to claim 1, where R b is an amino or piperidinyl carbonyl.

8. A compound or a pharmaceutically acceptable salt thereof according to claim 1, where R 1 is a benzodioxolyl.

9. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein R 2 is methyl, fluorine, phenyl, naphthyl (naphthalenyl), furanyl, pyridinyl, isoindolinone, benzodioxolyl, dihydrobenzodioxinyl, benzofuranyl or indazolyl and R 2-1 is methoxy, chlorine, fluorine or hydroxy.

10. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein R 3 is phenyl, pyridinyl or benzodioxolyl and R 3-1 is methoxy, chlorine, hydroxy or cyano.

11. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein L is -NH-, -NHCH2-, -NH(CH2)2-, NHC(O)-, -NHSO2-, or -S-.

12. The compound or pharmaceutically acceptable salt thereof according to claim 1, where R 4 is phenyl, naphthyl (naphthalenyl), furanyl, pyrazolyl, dihydropyridinyl, pyridinyl, pyrimidinyl, pyridinone, pyrimidinone, isoxazolyl, piperidinyl, benzodioxolyl, isoindolinone, dihydroisoquinolinone, benzofuranyl, benzothiophenyl, indolyl, indazolyl, quinolinyl, quinolinone, isoquinolinone, dihydropyrrolopyridinone, benzoisoxazolone, dihydronaphthyridinone, benzoxazolyl, benzoisoxazolyl, triazolopyridinone, phthalazinone, quinazolinone or pyridopyrimidinone.

13. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein Q is methyl, propyl, isopropyl, fluorine, chlorine, bromine, hydroxy, trifluoromethyl, methoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR 5 , CH2R 5 , NR 5 R 6 , C(O)R 5 , C(O)OR 5 , C(O)NR 5 R 6 , NHC(O)R 5 , NHC(O)CH2R 5 , NHC(O)(CH2)2R 5 , NHC(O)CH2OR 5 , NHC(O)CH2NR 5 R 6 , NHCH2CH2R 5 , NR 5 C(O)R 6 , tetrazolyl, oxadiazolyl, oxadiazolyl, furyl, thienyl, imidazolyl, pyrazolyl, isoxazolyl, thiazolyl, oxo-thiadiazolyl, thioxo-oxadiazolyl, pyridinyl, pyrimidinyl, azetidinyl, oxazolidinone, piperidinyl, piperazinyl, morpholino, azaspiroheptanyl, azaspirooctanyl, azaspirononanil, azabicycloheptanyl or azabicyclooctanyl, R 5is H, methyl, ethyl, butyl, cyclopropyl, cyclohexane, methoxy, amino, phenyl, benzyl, imidazolyl, oxadiazolyl, oxadiazolone, pyridinyl, pyrimidinyl, azetidinyl, piperidinyl, piperidinone, piperazinyl, morpholino, thiazolidinedione, piperazinone, piperazinedione, azaspiroheptanyl or azaspirononanyl and R 6 represents H, methyl, ethyl, propyl, isopropyl, sulfonyl, pyrazolyl, pyridinyl, pyridazinyl, azetidinyl or piperidinyl.

14. The compound or pharmaceutically acceptable salt thereof according to claim 1, where R 7 is methyl, propyl, isopropyl, cyclopropyl, fluoro, chloro, difluoromethyl, trifluoromethyl, hydroxy, methoxy, hydroxymethyl, cyano, amino, dimethylamino, methyl carboxylate, tert-butyl carboxylate, nitro, isoxazolyl, thiazolyl, pyridinyl or oxadiazolylmethyl.

15. The compound or pharmaceutically acceptable salt thereof according to claim 1, wherein the compound represented by Formula 1 is selected from the group consisting of the following: [1] 7-phenylpyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [2] (7-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [3] methyl 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate, [4] (7-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [5] (7-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [6] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [7] (7-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [8] (7-(2-chloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [9] (7-(5-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [10] 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoic acid, [11] methyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate, [12] (7-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [13] (7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [14] (7-(4-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [15] 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [16] (7-(6-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [17] (7-(6-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [18] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinonitrile, [19] (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [20] (7-(4-methoxy-3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [21] (7-(3-chloro-4-hydroxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone], [22] 2-fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [23] 2-(dimethylamino)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [24] (7-(3,4-dimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [25] (7-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [26] (7-(3-(morpholine-4-carbonyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [27] N-methyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [28] N-isopropyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [29] azetidin-1-yl(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone, [30] N-(2-methoxyethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [31] N-(2-(dimethylamino)ethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [32] N-(cyclopropylmethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [33] N-(1-methylpiperidin-4-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [34] piperazin-1-yl(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone, [35] tert-butyl 4-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoyl)piperazine-1-carboxylate, [36] N-(2-cyanoethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [37] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide, [38] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide, [39] (7-(5-(morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [40] N-methyl-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [41] azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [42] (3-hydroxyazetidin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [43] (7-(5-(2-azaspiro[3,3]heptan-2-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [44] (3,3-difluoroazetidin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [45] N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [46] N-(cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [47] N-(1-methylpiperidin-4-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [48] ​​piperazin-1-yl(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [49] (4-methylpiperazin-1-yl)(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [50] (4-isopropylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [51] N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [52] N-(cyanomethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [53] 5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)nicotinamide, [54] 5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)nicotinamide, [55] N-(isoxazol-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [56] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridazin-4-yl)nicotinamide, [57] 5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(thiazol-5-ylmethyl)nicotinamide, [58] N-methyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [59] N,N-dimethyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [60] N-isopropyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [61] azetidin-1-yl(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone, [62] N-(2-methoxyethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [63] N-(2-(dimethylamino)ethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [64] N-(cyclopropylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [65] N-(1-methylpiperidin-4-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [66] piperazin-1-yl(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone, [67] (4-methylpiperazin-1-yl)(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone, [68] (4-isopropylpiperazin-1-yl)(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone, [69] N-(2-cyanoethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [70] N-(cyanomethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [71] 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide, [72] 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide, [73] N-(isoxazol-3-ylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide, [74] (7-(6-(morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [75] N-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [76] N-isopropyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [77] azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone, [78] N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [79] N-(2-(dimethylamino)ethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [80] N-(cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [81] N-(1-methylpiperidin-4-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [82] piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone, [83] (4-methylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone, [84] (4-isopropylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone, [85] N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [86] N-(cyanomethyl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [87] 5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)picolinamide, [88] 5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)picolinamide, [89] N-(isoxazol-3-ylmethyl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [90] N-(2-cyanoethyl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)furan-2-carboxamide, [91] 3-methoxy-N-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide, [92] 1-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)urea, [93] 1-methyl-N-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidin-4-carboxamide, [94] N-(3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridine-7-yl)phenyl)cyclopropanecarboxamide, [95] N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide, [96] N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide, [97] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)acetamide, [98] 3-methoxy-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide, [99] 1-methyl-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide, [100] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropanecarboxamide, [101] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide, [102] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide, [103] 3-methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)propanamide, [104] 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide, [105] 2-oxo-N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)piperidin-4-carboxamide, [106] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide, [107] (7-(6-((3-methoxypropyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [108] (7-(6-morpholinopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [109] (7-(6-(isopropylamino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [110] piperidin-1-yl(7-(6-(piperidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone, [111] (7-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [112] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanesulfonamide, [113] (7-(3-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [114] (7-(4-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [115] 3-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one, [116] 3-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one, [117] 3-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-1,2,4-oxadiazol-5(4H)-one, [118] (7-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [119] (Z)-5-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzylidene)thiazolidine-2,4-dione, [120] tert-butyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate, [121] (7-(benzo[d][1,3]dioxol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [122] (7-(benzofuran-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [123] (7-(benzofuran-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [124] (7-(benzo[b]thiophen-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [125] (7-(1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [126] (7-(1H-indol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [127] (7-(benzofuran-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [128] (7-(naphthalen-1-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [129] (7-(naphthalen-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [130] piperidin-1-yl(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone, [131] 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one, [132] 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one, [133] 2-isopropyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one, [134] 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one, [135] 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one, [136] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one, [137] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one, [138] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one, [139] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one, [140] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [141] 2-methyl-6-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [142] 2-Isopropyl-6-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [143] 5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [144] 2-methyl-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [145] 6-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinolin-2(1H)-one, [146] 4-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)benzonitrile, [147] 3-((3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)pyridin-2(1H)-one, [148] piperidin-1-yl(7-((pyrimidin-2-ylmethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone, [149] piperidin-1-yl(7-((2-(pyridin-4-yl)ethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone, [150] (7-((1-methylpiperidin-4-yl)amino)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [151] 1-(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)pentan-1-one, [152] 4-(3-acetylpyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [153] 4-(3-(2-hydroxypropan-2-yl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [154] 7-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one, [155] 6-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [156] 4-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [157] (4-fluoropiperidin-1-yl)(7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)methanone, [158] cyclohexyl(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone, [159] 7-(2-amino-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one, [160] 7-(2-amino-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one, [161] (7-(3-chlorophenyl)-1H-indazol-3-yl)(piperidin-1-yl)methanone, [162] (8-(3-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone, [163] (8-(4-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone, [164] (8-(4-aminophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone, [165] (8-(3-chlorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone, [166] (8-(2-chloropyridin-4-yl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone, [167] (8-(3-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone, [168] (7-(4-methoxyphenyl)[1,2,3]triazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [169] (7-(3-chlorophenyl)-1H-indol-3-yl)(piperidin-1-yl)methanone, [170] (6-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [171] (6-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [172] (6-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [173] (5-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [174] (4-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-c]pyridin-2-yl)(piperidin-1-yl)methanone, [175] (4-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[2,3-c]pyridin-2-yl)(piperidin-1-yl)methanone, [176] (4-(benzo[d][1,3]dioxol-5-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl)(piperidin-1-yl)methanone, [177] (4-(benzo[d][1,3]dioxol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)(piperidin-1-yl)methanone, [178] (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [179] (5-(4-methoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [180] (5-(4-chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [181] (5-(3,4-dimethoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [182] (5-(4-fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [183] ​​(5-(furan-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [184] piperidin-1-yl(5-(pyridin-4-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)methanone, [185] (5-(3-chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [186] (5-(3-chloro-4-hydroxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [187] (2-(benzo[d][1,3]dioxol-5-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)(piperidin-1-yl)methanone, [188] (5-(benzofuran-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [189] (5-(naphthalen-2-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [190] (5-(1H-indazol-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone, [191] 2-(2-(piperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)isoindolin-1-one, [192] (3-fluoroazetidin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [193] N-(1-methyl-1H-pyrazol-3-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [194] (7-((3-methoxyphenyl)thio)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [195] 3-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one, [196] 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide, [197] 3-methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)propenamide, [198] 2-oxo-N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)piperidin-4-carboxamide, [199] 6-methyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one, [200] N-(azetidin-3-yl)-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [201] N-methylsulfonyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-3-carboxamide, [202] N-(1-methylazetidin-3-yl)-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide, [203] 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazin-2-one, [204] 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazine-2,6-dione, [205] 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carbonitrile, [206] (7-(6-(azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [207] 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-4(3H)-one, [208] (7-(6-(3-fluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [209] (7-(6-(3,3-difluoroazetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [210] (7-(6-(3-hydroxyazetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [211] 7-[[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridine-7-yl]amino]-3,4-dihydro-2H-isoquinoline-1-one, [212] 6-[[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridine-7-yl]amino]isoindoline-1-one, [213] (3-fluoroazetidine-1-yl)-[5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone, [214] 2-azaspiro[3,3]heptane-2-yl-[5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone, [215] (7-(6-(2-azabicyclo[2,2,1]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [216] (7-(6-(2-azabicyclo[2,2,2]octane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [217] (2-(6-(7-azabicyclo[2,2,1]heptane-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [218] (7-(6-(3-(dimethylamino)azetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [219] methyl 1-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)azetidine-3-carboxylate, [220] (7-(6-(2-azaspiro[3,3]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [221] (7-(6-(3-(hydroxymethyl)azetidine-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [222] (7-(6-(7-azaspiro[3,5]nonan-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [223] (7-(6-(6-azaspiro[3,4]octane-6-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [224] 7-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazine-1(2H)-one, [225] (6-hydroxy-2-azaspiro[3,3]heptan-2-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone, [226] 2-oxa-7-azaspiro[3,5]nonan-7-yl-[5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone, [227] (2-azabicyclo[2,2,1]heptan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone, [228] (2-azabicyclo[2,2,2]octan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone, [229] (7-azabicyclo[2,2,1]heptan-7-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone, [230] (3-hydroxyiminoazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone, [231] 6-(3-(4-fluoropiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methylisoindolin-1-one, [232] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one, [233] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1(2H)-one, [234] 6-(3-(4,4-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [235] 4-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-1H-pyrimidin-6-one, [236] 3-methyl-6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]pyrimidin-4-one, [237] (3,3-difluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone, [238] [7-[(4-chlorophenyl)methylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [239] 4-chloro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzamide, [240] 1,3,5-trimethyl-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrazole-4-sulfonamide, [241] 5-fluoro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-3-carboxamide, [242] [7-[2-(4-chlorophenyl)ethylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [243] 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid, [244] methyl 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylate, [245] 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one, [246] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one, [247] 3-[3-fluoro-5-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-4H-1,2,4-oxadiazol-5-one, [248] [7-[6-(azetidine-1-carbonyl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [249] [7-[5-fluoro-6-(morpholine-4-carbonyl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [250] 3-fluoro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridin-2-carboxamide, [251] 3-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one, [252] 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one, [253] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzaldehyde oxime, [254] 2-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile, [255] 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[2,3-d]pyrimidin-4(3H)-one, [256] 3-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[3,2-d]pyrimidin-4(3H)-one, [257] (7-(2-(3-fluoroazetidin-1-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [258] 3-chloro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid, [259] [7-(3-amino-1,2-benzoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [260] [7-(3-amino-1H-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [261] [7-(3-amino-1-methyl-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [262] 3-chloro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide, [263] [7-[5-fluoro-6-(5-methyl-1,2,4-oxadiazol-3-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [264] (7-(2-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [265] (7-(5-bromo-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [266] (7-(2,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [267] (7-(2-chloropyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [268] 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzo[d]isoxazol-3(2H)-one, [269] (7-(3-methoxybenzo[d]isoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [270] 2-(dimethylamino)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinonitrile, [271] (7-(6-fluoropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [272] (7-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [273] (7-(2,6-difluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [274] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide, [275] 3-[2-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one, [276] [7-[4-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [277] [7-[2-(azetidine-1-carbonyl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [278] N-(2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide, [279] (7-(3-chloro-5-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [280] 5,6-dimethyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-5,6-dihydro-7H-pyrrolo[3,4-b]pyridin-7-one, [281] (7-(6-chloro-5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [282] (7-(2,6-dichloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [283] (7-(5-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [284] (7-(5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [285] 3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile, [286] [7-[6-(azetidine-1-carbonyl)-5-chloro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [287] N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide, [288] (7-(5,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [289] (7-(5-chloro-6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [290] 2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [291] 3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [292] (7-(4-bromophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [293] 5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidine-2-carbonitrile, [294] [7-(2-hydroxypyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [295] 3-[3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one, [296] [7-[2-fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [297] 3-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1,2,4-oxadiazol-5(4H)-one, [298] (7-(5-chloro-2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [299] 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one, [300] [7-[4-(2-methylpyrazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [301] N-(3-chloro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide, [302] [7-[4-(3-furyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [303] [7-[3-fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [304] 3-[2-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one, [305] 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carbonitrile, [306] [7-[4-(2-hydroxypyrimidine-5-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [307] 5-[4-[3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridine-7-yl]phenyl]pyrimidine-2-carboxamide, [308] 3-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidine-2-yl)oxazolidin-2-one, [309] [7-(3-amino-1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [310] [7-(3-amino-1-methyl-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [311] N-(3-chloro-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide, [312] 3-nitro-5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile, [313] (7-(6-bromopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [314] (7-(6-chloropyridine-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [315] (7-(6-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [316] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [317] [7-[2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [318] (7-(5-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [319] (7-(5-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [320] [7-(3-amino-1,2-benzoxazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [321] 3-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidin-2-yl]-4H-1,2,4-oxadiazol-5-one, [322] (7-(3-fluoro-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [323] 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [324] [7-[4-(3,5-dimethylisoxazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [325] (7-(2-fluoro-5-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [326] N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide, [327] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyridin-3-yl)acetamide, [328] (7-(3,5-difluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [329] 3-(3-nitro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one, [330] (7-(3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [331] 3-(2,6-difluoro-4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one, [332] piperidin-1-yl(7-(6-(((2-(pyridin-3-yl)ethyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone, [333] 1,2-dimethyl-N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1H-imidazol-5-carboxamide, [334] N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)pyrimidine-5-carboxamide, [335] 5-fluoro-N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide, [336] (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methylpiperidin-1-yl)methanone, [337] (3-ethylpiperidin-1-yl)(7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone, [338] (7-(6-fluoropyridine-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-(trifluoromethyl)piperidin-1-yl)methanone, [339] 3-(5-(3-(3-(trifluoromethyl)piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [340] N-(2-nitrobenzyl)-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide, [341] (7-(3-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [342] (7-(3-nitro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [343] (7-(3-amino-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [344] (7-(6-(4-amino-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [345] (7-(3-(3-hydroxyazetidin-1-yl)-5-(isoxazol-4-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [346] 1-piperidyl-[7-[4-(1H-pyrazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone, [347] 1-piperidyl-[7-[4-(3-thienyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone, [348] [7-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [349] 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-3H-1,3,4-oxadiazol-2-one, [350] [7-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [351] [7-[4-(5-methylthiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [352] [7-[4-(1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [353] 3-(5-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [354] 3-(5-(3-(3-ethylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [355] (7-(6-(4-nitro-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [356] (7-(2-(4-amino-1H-pyrazol-1-yl)-6-bromopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [357] (7-(2-(3-hydroxyazetidin-1-yl)-6-(1-methyl-1H-pyrazol-5-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [358] 7-[4-(1,2-dimethylimidazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [359] [7-[4-(5-amino-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [360] 5-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one, [361] 1-piperidyl-[7-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone, [362] N-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide, [363] (7-(5-bromo-2-(3-(hydroxymethyl)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [364] [7-[6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [365] 1-piperidyl-[7-[6-(2-thioxo-3R-1,3,4-oxadiazol-5-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]methanone, [366] (7-(2-(isoxazol-4-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [367] 3-(6-(1-methyl-1H-pyrazol-5-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [368] 3-(6-(3,5-dimethylisoxazol-4-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [369] (7-(2-(1-methyl-1H-pyrazol-5-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [370] 3-(5'-fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[2,3'-bipyridin]-6-yl)oxazolidin-2-one, [371] (7-(2-(3,5-dimethylisoxazol-4-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [372] 3-(6-(2-methylpyrimidin-5-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [373] 5-[3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one, [374] (7-(5-(1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [375] (7-(6-(3-(dimethylamino)azetidin-1-yl)-5'-fluoro-[2,3'-bipyridin]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [376] (7-(5'-fluoro-6-morpholino-[2,3'-bipyridin]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [377] (7-(2-(2-methylpyrimidin-5-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [378] 6-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [379] [7-[5-fluoro-6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [380] [7-[5-fluoro-6-(1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [381] [7-[6-(3,5-dimethylisoxazol-4-yl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [382] 6-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [383] 3-(5-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [384] 3-(5-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one, [385] (R)-6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [386] (S)-6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [387] 6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [388] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetamide, [389] 2-phenyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide, [390] 6-(3-(2-azaspiro[3,3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [391] 6-(3-(6-azaspiro[3,4]octan-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [392] 6-(3-(7-azaspiro[3,5]nonane-7-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [393] 6-(3-(3-ethylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [394] [7-[5-fluoro-6-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [395] (7-(1-((1,2,4-oxadiazol-3-yl)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [396] 3-((4-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-1H-pyrazol-1-yl)methyl)-1,2,4-oxadiazol-5(4H)-one, [397] (7-(2-(1-((1,2,4-oxadiazol-3-yl)methyl)-1H-pyrazol-4-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [398] 6-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [399] [7-[2-(3,5-dimethylisoxazol-4-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [400] 6-(3-(3-isopropylpiperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [401] 6-(3-(1,2,3,6-tetrahydropyridin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [402] 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide, [403] N-(5-(3-(piperidin-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyrimidin-5-yl)acetamide, [404] [7-[2-[5-(difluoromethyl)-1-oxo-1,3,4-thiadiazol-2-yl]pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [405] 6-(3-(6-azaspiro[3,5]nonane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [406] 2-(4-chlorophenoxy)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide, [407] N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-2-pyrimidin-5-yl-acetamide, [408] N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-2-[6-(trifluoromethyl)-3-pyridyl]acetamide, [409] 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide, [410] 2-(4-chlorophenoxy)-N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]acetamide, [411] 6-(3-(6-fluoro-2-azaspiro[3,3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [412] 6-(3-(6,6-difluoro-2-azaspiro[3,3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one and [413] 3-hydroxy-5-[2-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-6-yl]pyridine-2-carbonitrile.

16. Use of a heterocyclic compound or a pharmaceutically acceptable salt thereof according to any one of claims 1 to 15 for the manufacture of a medicament for the prevention or treatment of a disease associated with 15-PGDH.

17. The use according to claim 16, wherein the 15-PGDH-associated disease is one or more selected from the group consisting of inflammatory disease (inflammatory bowel disease (ulcerative colitis, Crohn's disease), Behcet's disease, acute liver injury, acute kidney injury, acute lung injury, peptic ulcer (e.g., NSAID-induced ulcer), non-alcoholic fatty liver disease (NAFLD)), fibrosis (pulmonary fibrosis (idiopathic pulmonary fibrosis), renal fibrosis (glomerulosclerosis), cardiac fibrosis (myocardial fibrosis), liver fibrosis, myelofibrosis), myopathy (muscular dystrophy, muscle damage), anemia (aplastic anemia), circulatory system disease (kidney disease (chronic kidney disease, renal failure), stroke), cytopenia (immune cytopenia), radiation toxicity, systemic sclerosis, scars, wounds, hair loss, diabetes, stem cell and bone marrow transplantation or organ transplantation,Alzheimer's disease and Parkinson's disease, 18. A pharmaceutical composition for the prevention or treatment of a disease associated with 15-PGDH, comprising a therapeutically effective amount of a heterocyclic compound or a pharmaceutically acceptable salt thereof according to any one of claims 1-15 and a pharmaceutically acceptable additive.

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