Novel heterocyclic compounds

Abstract

The present invention provides novel heterocyclic compounds, their hydrates, solvates, or pharmaceutically acceptable salts as 15-PGDH inhibitors. The novel heterocyclic compounds of the present invention have been confirmed to exhibit excellent 15-PGDH inhibitory activity and to be usable for the prevention or treatment of 15-PGDH-related diseases. Therefore, the novel heterocyclic compounds of the present invention can be usefully used in the prevention or treatment of 15-PGDH-related diseases in the fields of medicine and pharmaceutical science.

Description

[Technical Field]

[0001] The present invention relates to novel heterocyclic compounds as 15-PGDH inhibitors. This application claims priority to Korean Patent Application No. 10-2023-0009009, filed on January 20, 2023, the entire contents of which are incorporated herein by reference. [Background technology]

[0002] Prostaglandins are physiologically active substances synthesized in vivo, distributed throughout organs and body fluids, and exert physiological effects even in minute amounts. Prostaglandins are fatty acid derivatives consisting of 20 carbon atoms, each consisting of a prostanoic acid skeleton with a five-membered ring at the center of its molecular structure. They are classified into groups A to J based on the chemical formula of the five-membered ring, and further into series 1 to 3 based on the number of double bonds in the two side chains. They are widely distributed in animal tissues and are known to be rapidly metabolized after being synthesized from polyunsaturated fatty acids. Depending on their form, prostaglandins can stimulate smooth muscle contraction. In some animals, they can lower or increase blood pressure and decrease or increase blood coagulation. They also promote membrane ion transport, stimulate inflammation, and suppress cardiovascular disease and viral infections.

[0003] 15-PGDH (15-hydroxyprostaglandin dehydrogenase) uses active prostaglandins such as PGD2, PGE1, PGE2, PGF2α, and PGI2 as substrates and is involved in their inactivation, for example, by converting them to 15-keto-PGE2, which catalyzes the oxidation of the hydroxyl group at the 15th position of PGE2.

[0004] The receptors corresponding to the substrates of 15-PGDH are widely distributed in the body due to their different expression sites, and are known to be involved in a variety of physiological functions in the body. For example, the substrates of 15-PGDH have anti-fibrotic, anti-inflammatory, blood circulation improving, proliferation promoting, stem cell proliferation promoting, smooth muscle contraction / relaxation, immunosuppressive, and bone metabolism effects. Therefore, 15-PGDH inhibitors are effective in treating fibrosis [pulmonary fibrosis (e.g., idiopathic pulmonary fibrosis), hepatic fibrosis, renal fibrosis, myocardial fibrosis, scleroderma, myelofibrosis, etc.], inflammatory diseases [chronic obstructive pulmonary disease (COPD), acute lung injury, sepsis, asthma and exacerbation of lung disease, inflammatory bowel disease (e.g., ulcerative colitis, Crohn's disease), peptic ulcer (e.g., NSAID-induced ulcer), autoinflammatory diseases (e.g., Behcet's disease), vascular inflammation syndrome, acute liver injury, acute kidney injury, non-alcoholic steatohepatitis (NASH), atopic dermatitis, psoriasis, interstitial cystitis, prostatitis syndrome (e.g., chronic prostatitis / chronic pelvic pain syndrome), etc.], cardiovascular diseases [pulmonary hypertension, angina pectoris, Myocardial infarction, heart failure, ischemic heart damage, chronic kidney disease, renal failure, stroke, peripheral circulatory disorders, etc.), wounds (diabetic ulcers, lacerations, pressure ulcers, acute mucosal injury in acute mucosal injury diseases including Stevens-Johnson syndrome, anti-cancer chemotherapy, immunotherapy or radiation, mucosal injury (mucositis and stomatitis) associated with graft-versus-host disease, etc.), autoimmune diseases (multiple sclerosis, rheumatoid arthritis, etc.), graft-versus-host disease (GVHD), hair growth, osteoporosis, ear diseases (hearing loss, tinnitus, dizziness, balance disorders, etc.), ophthalmological diseases (glaucoma, xerophthalmia, etc.), diabetes, underactive bladder, neutropenia, promotion of engraftment in stem cell and bone marrow transplants and organ transplants, neurogenesis and neuronal cell death (neuropsychiatric disorders, nerve injury, neurotoxicity, neuropathic pain, neurodegenerative diseases), muscle regeneration (muscular atrophy, muscular dystrophy) It is effective in the treatment or prevention of conditions related to muscular dystrophy, muscle damage, and cervical ripening. Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide 15-PGDH inhibitor compounds with novel structures that exhibit excellent 15-PGDH inhibitory activity.

[0006] Another object of the present invention is to provide a pharmaceutical composition for preventing or treating 15-PGDH-related diseases, which comprises the 15-PGDH inhibitor compound having the novel structure.

[0007] Another object of the present invention is to provide a method for preventing or treating a 15-PGDH-associated disease, which comprises administering a therapeutically effective amount of the 15-PGDH inhibitor compound having the novel structure to an individual in need thereof.

[0008] A further object of the present invention is to provide a use of the 15-PGDH inhibitor compound having the novel structure as an active ingredient in the manufacture of a medicament for the prevention or treatment of 15-PGDH-related diseases.

[0009] However, the problems to be solved by the present invention are not limited to the above-mentioned problems, and other technical problems not mentioned will be clearly understood by those skilled in the art to which the present invention pertains from the following description. [Means for solving the problem]

[0010] In order to solve the above problems, one aspect of the present invention provides a heterocyclic compound represented by the following chemical formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof. [ka] In the above formula, Ring A and ring B are fused to form a fused ring of two rings, X1, Y1, Y2, Y3 and Y4 are independently CH or N; X2 is CH, N or NH; Z1 and Z2 are C or N; at least one of X1, X2, Y1, Y2, Y3, Y4, Z1 and Z2 is N or NH; R a H, R a-1 C replaced by 1-6 Straight or branched chain alkyl, or C(O)R a-1 and R a-1 is C 1-6 Straight or branched chain alkyl, C 3-8 Cycloalkyl, hydroxy, R s or R u and R a-1 is one or more independent R a-2 or not replaced by, R a-2 is C 1-6 Straight or branched alkyl, halogen, C 1-4 is haloalkyl, wherein X1 is R b may be substituted or unsubstituted, and b is amino or C(O)R s and The Y1 is R 1 may be substituted or unsubstituted, and 1 is R f and The Y2 is R 2 or not replaced by, R 2 is C 1-6 Straight or branched alkyl, halogen, C 5-12 monocyclic or bicyclic aryl, R u or R f and R 2 is one or more independent R 2-1 or not replaced by, R 2-1 is C 1-4 alkoxy, halogen or hydroxy; The Y3 is R 3 or not replaced by, R 3 is C5-7 Aryl, R u or R f and R 3 is one or more independent R 3-1 or not replaced by, R 3-1 is C 1-4 alkoxy, halogen, hydroxy or cyano; The Y4 is R 4 or -LR 4 or not replaced by, The L is -NH(CH2) m -, -NHC(O)-, -NHSO2-, or -S-, wherein m is an integer of 0 to 3; R 4 is C 5-12 monocyclic or bicyclic aryl, R u , R s or R f and R 4 is unsubstituted or substituted independently by one or more Q; wherein Q is C 1-6 Straight or branched alkyl, halogen, hydroxy, C 1-4 Haloalkyl, C 1-4 Alkoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR 5 , CH2R 5 , N.R. 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 , N.R. 5 C(O)R 6 , R u or R s wherein p is an integer of 0 to 3, and Q is one or more independent R 7 or not replaced by, R 5 and R 6 are independently 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 and R 7 is 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 , R u C replaced by 1-4 Alkyl or R s and Q and R 7 The bond to is a single bond or a double bond, R s is a 4-10 membered monocyclic or bicyclic saturated heterocycloalkyl ring containing 1 to 3 heteroatoms selected from N, O and S, R u is a 5- to 7-membered unsaturated heterocycloalkyl ring containing 1 to 4 heteroatoms selected from N, O, and S; R f is a fused ring of two rings in which a 5- to 7-membered saturated or unsaturated heterocycloalkyl ring containing 1 to 2 heteroatoms selected from N, O, and S is fused with an aryl ring or a 5- to 7-membered heteroaryl ring containing 1 to 2 N atoms, R s , R u and R f is independently substituted with 1 to 2 oxo (O) or thioxo (S), or is unsubstituted.

[0011] In another aspect of the present invention, there is provided a pharmaceutical composition for preventing or treating a 15-PGDH-related disease, comprising the heterocyclic compound represented by Chemical Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof as an active ingredient.

[0012] In yet another aspect, the present invention provides a method for preventing or treating a 15-PGDH-associated disease, which comprises administering a therapeutically effective amount of a heterocyclic compound represented by Chemical Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof to an individual in need thereof.

[0013] In yet another aspect, the present invention provides use of the heterocyclic compound represented by Chemical Formula 1, its hydrate, its solvate, or its pharmaceutically acceptable salt as an active ingredient in the manufacture of a medicament for the prevention or treatment of a 15-PGDH-related disease.

[0014] In yet another aspect of the present invention, there is provided a pharmaceutical composition comprising the heterocyclic compound represented by Chemical Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient. [Effects of the Invention]

[0015] The novel heterocyclic compounds of the present invention have been confirmed to exhibit excellent 15-PGDH inhibitory activity, and therefore can be used for the prevention or treatment of 15-PGDH-related diseases.

[0016] Therefore, the novel heterocyclic compounds of the present invention can be usefully used in the fields of medicine and pharmaceutical science for the prevention or treatment of 15-PGDH-related diseases.

[0017] It should be understood that the effects of the present invention are not limited to the effects described above, but include all effects that can be inferred from the configuration of the invention described in the description of the present invention or the claims. DETAILED DESCRIPTION OF THE INVENTION

[0018] The present invention provides a heterocyclic compound represented by the following chemical formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof: [ka] X1, Y1, Y2, Y3 and Y4 are independently CH or N; X2 is CH, N or NH; Z1 and Z2 are C or N; at least one of X1, X2, Y1, Y2, Y3, Y4, Z1 and Z2 is N or NH; R a H, R a-1 C replaced by 1-6 Straight or branched chain alkyl, or C(O)R a-1 and R a-1 is C 1-6 Straight or branched chain alkyl, C 3-8 Cycloalkyl, hydroxy, R s or R u and R a-1 is one or more independent R a-2 or not replaced by, R a-2 is C 1-6 Straight or branched alkyl, halogen, C 1-4 is haloalkyl, wherein X1 is R b may be substituted or unsubstituted, and b is amino or C(O)R s and The Y1 is R 1 may be substituted or unsubstituted, and 1 is R f and The Y2 is R 2 or not replaced by, R 2 is C 1-6 Straight or branched alkyl, halogen, C 5-12 monocyclic or bicyclic aryl, R u or R fand R 2 is one or more independent R 2-1 or not replaced by, R 2-1 is C 1-4 alkoxy, halogen or hydroxy; The Y3 is R 3 or not replaced by, R 3 is C 5-7 Aryl, R u or R f and R 3 is one or more independent R 3-1 or not replaced by, R 3-1 is C 1-4 alkoxy, halogen, hydroxy or cyano; The Y4 is R 4 or -LR 4 or not replaced by, The L is -NH(CH2) m -, -NHC(O)-, -NHSO2-, or -S-, wherein m is an integer of 0 to 3; R 4 is C 5-12 monocyclic or bicyclic aryl, R u , R s or R f and R 4 is unsubstituted or substituted independently by one or more Q; wherein Q is C 1-6 Straight or branched alkyl, halogen, hydroxy, C 1-4 Haloalkyl, C 1-4 Alkoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR 5 , CH2R 5 , N.R. 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 , N.R. 5 C(O)R 6 , R u or R s wherein p is an integer of 0 to 3, and Q is one or more independent R 7 or not replaced by, R 5 and R 6 are independently 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 and R 7 is 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 , R u C replaced by 1-4 Alkyl or R s and Q and R 7 The bond to is a single bond or a double bond, R s is a 4-10 membered monocyclic or bicyclic saturated heterocycloalkyl ring containing 1 to 3 heteroatoms selected from N, O and S, R u is a 5- to 7-membered unsaturated heterocycloalkyl ring containing 1 to 4 heteroatoms selected from N, O, and S; R fis a fused ring of two rings in which a 5- to 7-membered saturated or unsaturated heterocycloalkyl ring containing 1 to 2 heteroatoms selected from N, O, and S is fused with an aryl ring or a 5- to 7-membered heteroaryl ring containing 1 to 2 N atoms, R s , R u and R f is independently substituted with 1 to 2 oxo (O) or thioxo (S), or is unsubstituted.

[0019] In one embodiment, the A ring may be pyrrole, pyrazole, imidazole, or triazole, and the B ring may be benzene, pyridine, pyrimidine, or triazine.

[0020] In one embodiment, the fused ring formed by the fusion of ring A and ring B may be indole, indazole, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, pyrazolopyridine, imidazopyridine, or triazolopyridine. More specifically, the fused ring formed by the fusion of ring A and ring B may be any one selected from the group consisting of the following chemical formulas:

[0021] [ka] In one embodiment, the R a is H, propyl, C(O)R a-1 and R a-1 is methyl, butyl, cyclohexyl, hydroxy, piperidinyl, azaspiroheptanyl, azaspirooctanyl, azaspirononanyl, azabicycloheptanyl, azabicyclooctanyl, azabicyclononanyl, or tetrahydropyridinyl, and said R a-2 can be methyl, ethyl, propyl, isopropyl, fluoro or trifluoromethyl.

[0022] In one embodiment, the R b can be amino or piperidinyl-carbonyl.

[0023] In one embodiment, the R 1 can be benzodioxolyl.

[0024] In one embodiment, the R 2 is methyl, fluoro, phenyl, naphthyl (naphthalenyl, furanyl, pyridinyl, isoindolinone, benzodioxolyl, dihydrobenzodioxinyl, benzofuranyl, or indazolyl, and 2-1 can be methoxy, chloro, fluoro or hydroxy.

[0025] In one embodiment, the R 3 is phenyl, pyridinyl or benzodioxolyl, 3-1 can be methoxy, chloro, hydroxy or cyano.

[0026] In one embodiment, L can be -NH-, -NHCH2-, -NH(CH2)2-, -NHC(O)-, -NHSO2-, or -S-.

[0027] In one embodiment, the R 4 can be phenyl, naphthyl (naphthalenyl), furanyl, pyrazolyl, dihydropyridinyl, pyridinyl, pyrimidinyl, pyridinone, pyrimidinone, isoxazolyl, piperidinyl, benzodioxolyl, isoindolinone, dihydroisoquinolinone, benzofuranyl, benzothiophenyl, indolyl, indazolyl, quinolinyl, quinolinone, isoquinolinone, dihydropyrrolopyridinone, benzisoxazolone, dihydronaphthyridinone, benzoxazolyl, benzisoxazolyl, triazolopyridinone, phthalazinone, quinazolinone, or pyridopyrimidinone.

[0028] In one embodiment, Q is methyl, propyl, isopropyl, fluoro, chloro, bromo, hydroxy, trifluoromethyl, methoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR 5 , CH2R 5 , N.R. 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 , N.R. 5 C(O)R 6 , tetrazolyl, oxadiazolyl, oxadiazolone, furyl, thienyl, imidazolyl, pyrazolyl, isoxazolyl, thiazolyl, oxo-thiadiazolyl, thioxo-oxadiazolyl, pyridinyl, pyrimidinyl, azetidinyl, oxazolidinone, piperidinyl, piperazinyl, morpholino, azaspiroheptanyl, azaspirooctanyl, azaspirononanyl, azabicycloheptanyl, or azabicyclooctanyl, wherein R 5 is H, methyl, ethyl, butyl, cyclopropyl, cyclohexane, methoxy, amino, phenyl, benzyl, imidazolyl, oxadiazolyl, oxadiazolone, pyridinyl, pyrimidinyl, azetidinyl, piperidinyl, piperidinone, piperazinyl, morpholino, thiazolidinedione, piperazinone, piperazine-dione, azaspiroheptanyl, or azaspirononanyl, and 6 can be H, methyl, ethyl, propyl, isopropyl, sulfonyl, pyrazolyl, pyridinyl, pyridazinyl, azetidinyl or piperidinyl.

[0029] In one embodiment, the R 7 may 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.

[0030] In defining compounds of Formula 1 herein, the following definitions apply unless otherwise specified.

[0031] The term "alkyl" refers to a straight or branched chain saturated hydrocarbon having a C 1-10 Alkyl is preferred, for example, alkyl includes, but is not limited to, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, 3-methylhexyl, 2,2-dimethylpentyl, 2,3-dimethylpentyl, n-heptyl, n-octyl, n-nonyl, and n-decyl.

[0032] The term "cycloalkyl" refers to a partially or fully saturated monocyclic or fused ring hydrocarbon, 3-10 Cycloalkyl is preferred, including, but not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexynyl, and the like.

[0033] The term "hydroxy" or "hydroxy" is defined as -OH, and the term "alkoxy", unless otherwise defined, means an alkyloxy radical in which the hydrogen atom of a hydroxy group is replaced by 1 to 10 alkyl groups.

[0034] The term "halogen" or "halo" means fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

[0035] The terms "haloalkyl" and "haloalkoxy" mean an alkyl or alkoxy substituted with one or more halogen atoms.

[0036] The term "heteroatom" means N, O, or S.

[0037] The term "aryl" means an aromatic hydrocarbon, including polycyclic aromatic ring systems in which a carbocyclic aromatic ring or heteroaryl ring is fused to one or more other rings. 5-12Aryl, more preferably C 5-10 Aryl. For example, the aryl includes, but is not limited to, phenyl, naphthyl, tetrahydronaphthyl, etc. Also included are groups in which a heteroaryl ring is fused to a cycloalkyl or non-aromatic heterocycle, such as indanyl or tetrahydrobenzopyranyl.

[0038] The term "heteroaryl" or "aromatic heterocycle" refers to a heterocyclic ring containing one or more heteroatoms selected from N, O, and S as ring atoms, and is not limited to benzo or C 3-8 It means a 3- to 12-membered, more preferably 5- to 10-membered, aromatic hydrocarbon that forms a single ring or a fused ring that can be fused with a cycloalkyl. For example, the 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.

[0039] Specific examples of the heterocyclic compounds according to the present invention are as follows: [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-(piperidine-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-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

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

[44] (3,3-difluoroazetidin-1-yl)(5-(3-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[48] ​​Piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[49] (4-methylpiperazin-1-yl)(5-(3-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)nicotinamide,

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

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

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

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

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

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

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

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

[94] N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-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,

[0100] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropanecarboxamide,

[0101] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide,

[0102] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide,

[0103] 3-methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)propanamide,

[0104] 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide,

[0105] 2-oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)piperidine-4-carboxamide,

[0106] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide,

[0107] (7-(6-((3-methoxypropyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0108] (7-(6-morpholinopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0109] (7-(6-(isopropylamino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0110] Piperidin-1-yl(7-(6-(piperidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0111] (7-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0112] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanesulfonamide,

[0113] (7-(3-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0114] (7-(4-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0115] 3-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0116] 3-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0117] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-1,2,4-oxadiazol-5(4H)-one,

[0118] (7-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0119] (Z)-5-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzylidene)thiazolidine-2,4-dione,

[0120] tert-butyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate,

[0121] (7-(benzo[d][1,3]dioxol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0122] (7-(benzofuran-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0123] (7-(benzofuran-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0124] (7-(benzo[b]thiophen-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0125] (7-(1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0126] (7-(1H-indol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0127] (7-(benzofuran-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0128] (7-(naphthalen-1-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0129] (7-(naphthalen-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0130] Piperidin-1-yl(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0131] 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0132] 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0133] 2-isopropyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0134] 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one,

[0135] 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one,

[0136] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0137] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0138] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one,

[0139] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one,

[0140] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0141] 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0142] 2-isopropyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0143] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0144] 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0145] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinolin-2(1H)-one,

[0146] 4-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)benzonitrile,

[0147] 3-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)pyridin-2(1H)-one,

[0148] piperidin-1-yl(7-((pyrimidin-2-ylmethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0149] piperidin-1-yl(7-((2-(pyridin-4-yl)ethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0150] (7-((1-methylpiperidin-4-yl)amino)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0151] 1-(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)pentan-1-one,

[0152] 4-(3-acetylpyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0153] 4-(3-(2-hydroxypropan-2-yl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0154] 7-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0155] 6-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0156] 4-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0157] (4-fluoropiperidin-1-yl)(7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0158] cyclohexyl(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone,

[0159] 7-(2-amino 3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one,

[0160] 7-(2-amino 3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one,

[0161] (7-(3-chlorophenyl)-1H-indazol-3-yl)(piperidin-1-yl)methanone,

[0162] (8-(3-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0163] (8-(4-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0164] (8-(4-aminophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0165] (8-(3-chlorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0166] (8-(2-chloropyridin-4-yl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0167] (8-(3-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0168] (7-(4-methoxyphenyl)-[1,2,3]triazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0169] (7-(3-chlorophenyl)-1H-indol-3-yl)(piperidin-1-yl)methanone,

[0170] (6-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0171] (6-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0172] (6-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0173] (5-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0174] (4-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-c]pyridin-2-yl)(piperidin-1-yl)methanone,

[0175] (4-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[2,3-c]pyridin-2-yl)(piperidin-1-yl)methanone,

[0176] (4-(benzo[d][1,3]dioxol-5-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl)(piperidin-1-yl)methanone,

[0177] (4-(benzo[d][1,3]dioxol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)(piperidin-1-yl)methanone,

[0178] (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0179] (5-(4-methoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0180] (5-(4-chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0181] (5-(3,4-dimethoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0182] (5-(4-fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0183] (5-(furan-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0184] Piperidin-1-yl(5-(pyridin-4-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)methanone,

[0185] (5-(3-chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0186] (5-(3-chloro-4-hydroxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0187] (2-(benzo[d][1,3]dioxol-5-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)(piperidin-1-yl)methanone,

[0188] (5-(benzofuran-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0189] (5-(naphthalen-2-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0190] (5-(1H-indazol-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone,

[0191] 2-(2-(piperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)isoindolin-1-one,

[0192] (3-fluoroazetidin-1-yl)(5-(3-piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone,

[0193] N-(1-methyl-1H-pyrazol-3-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide,

[0194] (7-((3-methoxyphenyl)thio)(pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0195] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5-(6H)-one,

[0196] 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide,

[0197] 3-methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)propenamide,

[0198] 2-oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)piperidine-4-carboxamide,

[0199] 6-methyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5-(6H)-one,

[0200] N-(azetidin-3-yl)-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]nicotinamide,

[0201] N-methylsulfonyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide,

[0202] N-(1-methylazetidin-3-yl)-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide,

[0203] 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazin-2-one,

[0204] 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazine-2,6-dione,

[0205] 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carbonitrile,

[0206] (7-(6-(azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0207] 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-4(3H)-one,

[0208] (7-(6-(3-fluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0209] (7-(6-(3,3-difluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0210] (7-(6-(3-hydroxyazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0211] 7-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino 3,4-dihydro-2H-isoquinolin-1-one,

[0212] 6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]isoindolin-1-one,

[0213] (3-fluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone,

[0214] 2-Azaspiro[3,3]heptan-2-yl-[5-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone,

[0215] (7-(6-(2-azabicyclo[2.2.1]heptan-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0216] (7-(6-(2-azabicyclo[2.2.2]octan-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0217] (7-(6-(7-azabicyclo[2.2.1]heptan-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0218] (7-(6-(3-(dimethylamino)azetidin-1-yl)(pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0219] methyl 1-(5-(3-(piperidine-1-carbonyl)(pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)azetidine-3-carboxylate,

[0220] (7-(6-(2-azaspiro[3.3]heptan-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0221] (7-(6-(3-(hydroxymethyl)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0222] (7-(6-(7-azaspiro[3.5]nonan-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0223] (7-(6-(6-azaspiro[3.4]octan-6-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0224] 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1-(2H)-one,

[0225] (6-hydroxy-2-azaspiro[3.3]heptan-2-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone,

[0226] 2-oxa-7-azaspiro[3.5]nonan-7-yl-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone,

[0227] (2-azabicyclo[2.2.1]heptan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone,

[0228] (2-azabicyclo[2.2.2]octan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone,

[0229] (7-azabicyclo[2.2.1]heptan-7-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone,

[0230] (3-hydroxyiminoazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone,

[0231] 6-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methylisoindolin-1-one,

[0232] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-6,7-dihydro-5H-pyrrolo[3,4-b]pyridin-5-one,

[0233] 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1(2H)-one,

[0234] 6-(3-(4,4-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0235] 4-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-1H-pyrimidin-6-one,

[0236] 3-methyl-6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]pyrimidin-4-one,

[0237] (3,3-difluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone,

[0238] [7-[(4-chlorophenyl)methylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0239] 4-chloro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzamide,

[0240] 1,3,5-trimethyl-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrazolo-4-sulfonamide,

[0241] 5-fluoro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide,

[0242] [7-[2-(4-chlorophenyl)ethylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0243] 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid,

[0244] methyl 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylate,

[0245] 3-methyl-6-(3-piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one,

[0246] 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,

[0247] 3-[3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]2-pyridyl]-4H-1,2,4-oxadiazol-5-one,

[0248] [7-[6-(azetidine-1-carbonyl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0249] [7-[5-fluoro-6-(morpholine-4-carbonyl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0250] 3-fluoro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide,

[0251] 3-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one,

[0252] 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,

[0253] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzaldehyde oxime,

[0254] 2-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile,

[0255] 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[2,3-d]pyrimidin-4(3H)-one,

[0256] 3-methyl-7-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[3,2-d]pyrimidin-4(3H)-one,

[0257] (7-(2-(3-fluoroazetidin-1-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0258] 3-chloro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid,

[0259] [7-(3-amino-1,2-benzoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0260] [7-(3-amino-1H-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0261] [7-(3-amino-1-methyl-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0262] 3-chloro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide,

[0263] [7-[5-fluoro-6-(5-methyl-1,2,4-oxadiazol-3-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0264] (7-(2-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0265] (7-(5-bromo-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0266] (7-(2,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0267] (7-(2-chloropyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0268] 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzo[d]isoxazol-3(2H)-one,

[0269] (7-(3-methoxybenzo[d]isoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0270] 2-(dimethylamino)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinonitrile,

[0271] (7-(6-fluoropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0272] (7-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0273] (7-(2,6-difluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0274] N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide,

[0275] 3-[2-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one,

[0276] [7-[4-fluoro-3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0277] [7-[2-(azetidine-1-carbonyl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0278] N-(2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide,

[0279] (7-(3-chloro-5-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0280] 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,

[0281] (7-(6-chloro-5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0282] (7-(2,6-dichloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0283] (7-(5-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0284] (7-(5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0285] 3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile,

[0286] [7-[6-(azetidine-1-carbonyl)-5-chloro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0287] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide,

[0288] (7-(5,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl](piperidin-1-yl)methanone,

[0289] (7-(5-chloro-6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0290] 2,6-difluoro-4-(3-(piperidine-1-carbonyl(pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0291] 3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0292] (7-(4-bromophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0293] 5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidine-2-carbonitrile,

[0294] [7-(2-hydroxypyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0295] 3-[3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one,

[0296] [7-[2-fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0297] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1,2,4-oxadiazol-5-(4H)-one,

[0298] (7-(5-chloro-2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0299] 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0300] [7-[4-(2-methylpyrazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0301] N-(3-chloro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide,

[0302] [7-[4-(3-furyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone],

[0303] [7-[3-fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0304] 3-[2-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one,

[0305] 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carbonitrile,

[0306] [7-[4-(2-hydroxypyrimidin-5-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0307] 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carboxamide,

[0308] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-2-yl)oxazolidin-2-one,

[0309] 7-(3-amino-1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0310] [7-(3-amino-1-methyl-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0311] N-(3-chloro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide,

[0312] 3-nitro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

[0313] (7-(6-bromopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0314] (7-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0315] (7-(6-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0316] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0317] [7-[2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0318] (7-(5-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0319] (7-(5-(5-methyl-1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0320] [7-(3-amino-1,2-benzoxazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0321] 3-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidin-2-yl]-4H-1,2,4-oxadiazol-5-one,

[0322] (7-(3-fluoro-5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0323] 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0324] [7-[4-(3,5-dimethylisoxazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0325] (7-(2-fluoro-5-(1-methyl-1H-pyrazol-5-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0326] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide,

[0327] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyridin-3-yl)acetamide,

[0328] (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,

[0329] 3-(3-nitro-5-(3-piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0330] (7-(3-(5-methyl-1,2,4-oxadiazol-3-yl)-5-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0331] 3-(2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one,

[0332] piperidin-1-yl(7-(6-((2-pyridin-3-yl)ethyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0333] 1,2-dimethyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1H-imidazole-5-carboxamide,

[0334] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)pyrimidine-5-carboxamide,

[0335] 5-fluoro-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide,

[0336] (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methylpiperidin-1-yl)methanone,

[0337] (3-ethylpiperidin-1-yl)(7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone,

[0338] (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-(trifluoromethyl)piperidin-1-yl)methanone,

[0339] 3-(5-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0340] N-(2-nitrobenzyl)-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide,

[0341] (7-(3-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0342] (7-(3-nitro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0343] (7-(3-amino5-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0344] (7-(6-(4-amino-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0345] (7-(3-(3-hydroxyazetidin-1-yl)-5-(isoxazol-4-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0346] 1-piperidyl-[7-[4-(1H-pyrazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone,

[0347] 1-piperidyl-[7-[4-(3-thienyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone,

[0348] [7-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0349] 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-3H-1,3,4-oxadiazol-2-one,

[0350] [7-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0351] [7-[4-(5-methylthiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0352] [7-[4-(1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0353] 3-(5-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0354] 3-(5-(3-(3-ethylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0355] (7-(6-(4-nitro-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0356] (7-(2-(4-amino-1H-pyrazol-1-yl)-6-bromopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0357] (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,

[0358] [7-[4-(1,2-dimethylimidazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0359] [7-[4-(5-amino-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0360] 5-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one,

[0361] 1-piperidyl-[7-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone,

[0362] N-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide,

[0363] (7-(5-bromo-2-(3-(hydroxymethyl)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0364] [7-[6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0365] 1-piperidyl-[7-[6-(2-thioxo-3H-1,3,4-oxadiazol-5-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]methanone,

[0366] (7-(2-(isoxazol-4-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0367] 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,

[0368] 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,

[0369] (7-(2-(1-methyl-1H-pyrazol-5-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0370] 3-(5'-fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[2,3'-bipyridin]-6-yl)oxazolidin-2-one,

[0371] (7-(2-(3,5-dimethylisoxazol-4-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0372] 3-(6-(2-methylpyrimidin-5-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0373] 5-[3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one,

[0374] (7-(5-(1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0375] (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,

[0376] (7-(5'-fluoro-6-morpholino-[2,3'-bipyridin]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0377] (7-(2-(2-methylpyrimidin-5-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0378] 6-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0379] [7-[5-fluoro-6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0380] [7-[5-fluoro-6-(1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0381] [7-[6-(3,5-dimethylisoxazol-4-yl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0382] 6-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0383] 3-(5-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0384] 3-(5-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one,

[0385] (R)-6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0386] (S)-6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0387] 6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0388] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(6-(trifluoromethyl)pyridin-3-yl)acetamide,

[0389] 2-phenyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide,

[0390] 6-(3-(2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0391] 6-(3-(6-azaspiro[3.4]octane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0392] 6-(3-(7-azaspiro[3.5]nonane-7-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0393] 6-(3-(3-ethylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0394] [7-[5-fluoro-6-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0395] (7-(1-((1,2,4-oxadiazol-3-yl)methyl)-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0396] 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,

[0397] (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,

[0398] 6-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0399] [7-[2-(3,5-dimethylisoxazol-4-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone,

[0400] 6-(3-(3-isopropylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0401] 6-(3-(1,2,3,6-tetrahydropyridine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0402] 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide,

[0403] N-(5-(3-piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyrimidin-5-yl)acetamide,

[0404] [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],

[0405] 6-(3-(6-azaspiro[3.5]nonane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0406] 2-(4-chlorophenoxy)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide,

[0407] N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl-2-pyrimidin-5-yl-acetamide,

[0408] N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-2-[6-(trifluoromethyl)-3-pyridyl]acetamide,

[0409] 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide,

[0410] 2-(4-chlorophenoxy)-N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]acetamide,

[0411] 6-(3-(6-fluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0412] 6-(3-(6,6-difluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, and

[0413] 3-Hydro-5-[2-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-6-yl]pyridine-2-carbonitrile.

[0040] The compound represented by Chemical Formula 1 according to the present invention can be used in the form of a prodrug, hydrate, solvate, or pharmaceutically acceptable salt to enhance in vivo absorption or increase solubility. Therefore, the prodrug, hydrate, solvate, and pharmaceutically acceptable salt also fall within the scope of the present invention.

[0041] The term "prodrug" refers to a substance that is converted into the parent drug in vivo. Prodrugs are often used because, in some cases, they are easier to administer than the parent drug. For example, they may be bioavailable by oral administration, whereas the parent drug may not. A prodrug may also have improved solubility in pharmaceutical compositions over the parent drug. For example, a prodrug may be an in vivo hydrolyzable ester of a compound according to the invention and its pharmaceutically acceptable salt. Yet another example of a prodrug may be a short peptide (polyamino acid) bonded to an acid group that is metabolically converted to reveal the active site.

[0042] The term "hydrate" means a compound of the present invention or a salt thereof that contains a stoichiometric or non-stoichiometric amount of water bound by non-covalent intermolecular forces.

[0043] The term "solvate" refers to 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. Desirable solvents in this context include solvents that are volatile, non-toxic, and / or suitable for human administration.

[0044] The term "isomer" refers to a compound of the present invention or a salt thereof that has the same chemical or molecular formula but is structurally or sterically different. Such isomers include structural isomers such as tautomers, and stereoisomers such as R or S isomers with asymmetric carbon centers and geometric isomers (trans, cis). All of these isomers and mixtures thereof are included within the scope of the present invention.

[0045] The term "pharmaceutically acceptable salt" refers to a salt form of a compound that does not induce significant irritation to an organism to which the compound is administered and does not impair the biological activity and physical properties of the compound. The pharmaceutical salt includes acid addition salts formed with 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., and sulfonic acids such as methanesulfonic acid, ethanesulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc. For example, pharmaceutically acceptable carboxylate salts include metal salts or alkaline earth metal salts formed with lithium, sodium, potassium, calcium, magnesium, etc., amino acid salts such as lysine, arginine, guanidine, etc., and organic salts such as dicyclohexylamine, N-methyl-D-glucamine, tris(hydroxymethyl)methylamine, diethanolamine, choline, triethylamine, etc. The compound of Formula 1 according to the present invention can be converted into its salt by a conventional method.

[0046] The present invention provides a method for preparing the compound of Formula 1.

[0047] Reaction Schemes 1 to 55 are examples of methods for preparing the compound of Chemical Formula 1 of the present invention, but the preparation methods of Reaction Schemes 1 to 55 do not limit the methods for preparing the compound of Chemical Formula 1 of the present invention. The preparation methods of Reaction Schemes 1 to 55 are merely examples, and it is obvious that they can be easily modified by those skilled in the art depending on the specific substituents.

[0048] The present invention also provides a pharmaceutical composition for preventing or treating 15-PGDH-related diseases, comprising the heterocyclic compound represented by Chemical Formula 1, its hydrate, its solvate, or a pharmaceutically acceptable salt thereof as an active ingredient.

[0049] The present invention also provides a method for preventing or treating a 15-PGDH-associated disease, which comprises administering a therapeutically effective amount of the heterocyclic compound represented by Chemical Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof to an individual in need thereof.

[0050] The present invention also provides a use of the heterocyclic compound represented by Chemical Formula 1, its hydrate, its solvate, or its pharmaceutically acceptable salt as an active ingredient in the manufacture of a medicament for the prevention or treatment of a 15-PGDH-related disease.

[0051] In one embodiment, the 15-PGDH-related disease is an inflammatory disease (inflammatory bowel disease (e.g., ulcerative colitis, Crohn's disease), chronic obstructive pulmonary disease (COPD), Behcet's disease, acute liver injury, acute kidney injury, acute lung injury, sepsis, asthma and exacerbation of pulmonary disease, peptic ulcer (e.g., NSAID-induced ulcer), vascular inflammatory syndrome, non-alcoholic steatohepatitis (NASH), atopic dermatitis, psoriasis, interstitial cystitis, prostatitis syndrome, etc.), fibrosis (pulmonary fibrosis (e.g., idiopathic pulmonary fibrosis), renal fibrosis (e.g., glomerulosclerosis), cardiac fibrosis (myocardial fibrosis), etc.). fibrosis, oral fibrosis, deltoid muscle fibrosis, liver fibrosis, myelofibrosis, scleroderma, etc.), autoimmune diseases (systemic lupus erythematosus, rheumatoid arthritis, autoimmune hepatitis, severe combined immunodeficiency syndrome (SCID), etc.), ophthalmological diseases (xerophthalmia, conjunctivitis, keratitis, etc.), thrombocytopenia (drug-induced thrombocytopenia, autoimmune thrombocytopenia, idiopathic thrombocytopenia due to viral infection, etc.), muscle diseases (muscle atrophy, muscle injury, muscular dystrophy, etc.), anemia (aplastic anemia, anemia of chronic disease, Fanconi anemia, β-thalassemia or genital Anemia of unknown etiology, etc.), cardiovascular disease (heart disease (angina pectoris, heart failure, myocardial infarction, etc.), kidney disease (chronic kidney disease, renal failure, etc.), stroke, pulmonary hypertension, peripheral circulatory disorders, etc.), neuronal cell death (neuropsychiatric disorders, neurodegenerative diseases, nerve damage, etc.), cytopenia (immune cytopenia, neutropenia, lymphopenia, etc.), osteoporosis, fractures, leukemia (acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML), etc.), lymphoma (Hodgkin's lymphoma, non-Hodgkin's lymphoma, etc.), toxicity due to radiation exposure, The disease may be 5-PGDH-expressing cancer, multiple myeloma, paroxysmal nocturnal hemoglobinuria (PNH), pure red cell aplasia, megakaryocytosis, Wiskott-Aldrich syndrome, sickle cell disease, Hurler syndrome, adrenoleukodystrophy, metachromatic leukodystrophy, myelodysplasia, Duchenne muscular dystrophy, solid tumors, chronic granulomatous disease, systemic sclerosis, scars, wounds, ear diseases (such as dizziness, tinnitus, and balance disorders), hair loss, skin aging, periodontal disease, diabetes, stem cell and bone marrow transplants or organ transplants, cervical ripening, Alzheimer's disease, and Parkinson's disease.

[0052] The 15-PGDH inhibitory activity of the heterocyclic compounds of the present invention was measured, and it was confirmed that they exhibited excellent 15-PGDH inhibitory activity.

[0053] The present invention also provides a pharmaceutical composition comprising the heterocyclic compound represented by Chemical Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable excipient.

[0054] The additives may contain pharmaceutically acceptable carriers or diluents, and can be formulated into oral dosage forms such as acids, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols, external preparations, suppositories, and sterile injection solutions by conventional methods.

[0055] The pharmaceutically acceptable carriers include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, acacia gum, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, mineral oil, etc. Also included are diluents or excipients such as fillers, extenders, binders, wetting agents, disintegrants, surfactants, etc. Oral solid preparations include tablets, pills, powders, granules, capsules, etc., and such solid preparations contain at least one or more excipients, such as starch, calcium carbonate, sucrose or lactose, gelatin, etc., and may also contain lubricants such as magnesium stearate and talc. Oral liquid preparations include suspensions, internal solutions, emulsions, syrups, etc., and may contain diluents such as water and liquid paraffin, wetting agents, sweeteners, flavorings, preservatives, etc. Parenteral preparations include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, creams, lyophilized preparations, and suppositories, and non-aqueous solvents and suspensions 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, laurin butter, glycerogelatin, etc.

[0056] The dosage of the active ingredient contained in the pharmaceutical composition of the present invention varies depending on the patient's condition and weight, the severity of the disease, the form of the active ingredient, the route of administration, and the duration of administration, and can be adjusted appropriately for each patient. For example, the active ingredient can be administered at a dose of 0.0001 to 1,000 mg / kg per day, preferably 0.001 to 100 mg / kg per day, and can be administered once or in several divided doses per day. Furthermore, the pharmaceutical composition of the present invention can contain the active ingredient in a weight percentage of 0.001 to 90% of the total weight of the composition.

[0057] The pharmaceutical composition of the present invention can be administered to mammals such as rats, mice, livestock, and humans by various routes, for example, orally, intraperitoneally, rectally, or by intravenous, intramuscular, subcutaneous, intrauterine, intradural, or intracerebroventricular injection.

[0058] The present invention will be described in more detail below with reference to examples and experimental examples. However, the following examples and experimental examples are intended to illustrate the present invention and are not intended to limit the scope of the present invention.

[0059] Example 1. 7-phenylpyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] 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 (18.5 mL, 18.5 mmol) dissolved in 1 M tetrahydrofuran was slowly added and stirred for 30 minutes. Iodine (1.878 g, 7.4 mmol) dissolved in tetrahydrofuran (5 mL) was added to the reaction solution and stirred for 30 minutes. The temperature was gradually increased to room temperature and then stirred for 12 hours. After completion of the reaction, saturated aqueous sodium bicarbonate (50 mL) was added, and the mixture was extracted with dichloromethane (50 mL × 3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. After solidification with a small amount of dichloromethane, the product was filtered and air-dried to obtain the target compound 1-1 (1.86 g, 94%).

[0060] 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 stirred at room temperature for 10 minutes. Piperidine (0.7 mL, 7.1 mmol) was added to the reaction solution and stirred for 4 hours. After completion of the reaction, the reaction solution was concentrated and diluted with ethyl acetate (100 mL). The solution was washed sequentially with water (50 mL), saturated aqueous ammonium chloride (50 mL), saturated aqueous sodium bicarbonate (50 mL), and brine (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The product was solidified with a diethyl ether / ethyl acetate (10:1) solution (20 mL), filtered, and air-dried 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, Hexafluorophosphate Azabenzotriazole Tetramethyl Uronium), DIPEA(N,N-Diisopropylethylamine)] Step 1-3: Compound 1-2 (70 mg, 0.19 mmol) was dissolved in 1,4-dioxin (7 mL), followed by the addition of benzeneboronic acid (24 mg, 0.19 mmol), tetrakis(triphenylphosphine)palladium (57 mg, 0.04 mmol), and 2 M aqueous potassium carbonate (0.19 mL, 0.39 mmol). After flushing with nitrogen for 10 minutes, 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 removed by filtration through diatomaceous earth (Celite), and the filtrate was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated by column chromatography to obtain the target compound 1 (42.3 mg, 70%). 1H NMR(400MHz,DMSO-d6)δ(ppm):8.23(s,1H),7.90(ddd,J=16.6,8.4,2.0Hz,3H),7.60-7.45 (m,4H),7.16(dd,J=7.1,1.4Hz,1H),3.62(t,J=5.4Hz,4H),1.65(s,2H),1.60-1.43(m,4H). MS(ESI,LR)Calc. for C 19 H 20 NO[M+H] + :306.2,found:306.2

[0061] Example 2 (7-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 3. Methyl 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate Example 4 (7-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 5 (7-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 6. 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile Example 8 (7-(2-chloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 10. 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoic acid Example 11. Methyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate Example 12 (7-(4-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 13 (7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 15. 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile Example 16 (7-(6-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 18. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinonitrile Example 19 (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 20 (7-(4-methoxy-3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 21 (7-(3-chloro-4-hydroxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 22. 2-fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile Example 23. 2-(dimethylamino)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile Example 24 (7-(3,4-dimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 25 (7-(1-methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 120. tert-butyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate Example 121 (7-(benzo[d][1,3]dioxol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 122 (7-(benzofuran-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 123 (7-(benzofuran-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 124 (7-(benzo[b]thiophen-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 125 (7-(1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 126 (7-(1H-indol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 127 (7-(benzofuran-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 128 (7-(naphthalen-1-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 129 (7-(naphthalen-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 130. Piperidin-1-yl(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone Example 131. 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one Example 134. 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one Example 136. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one Example 138. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one Example 140. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 143. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 145. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinolin-2(1H)-one Example 195. 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5-(6H)-one Example 205. 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carbonitrile Example 207. 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-4(3H)-one Example 224. 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1-(2H)-one 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 Example 233. 6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1(2H)-one Example 244. Methyl 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylate Example 245. 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one 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 Example 251. 3-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one 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 Example 254. 2-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile Example 255. 3-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[2,3-d]pyrimidin-4(3H)-one Example 256. 3-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[3,2-d]pyrimidin-4(3H)-one Example 264 (7-(2-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 265. 7-(5-bromo-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 266 (7-(2,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 267 (7-(2-chloropyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 268. 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzo[d]isoxazol-3(2H)-one Example 269. (7-(3-methoxybenzo[d]isoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 270. 2-(dimethylamino)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinonitrile Example 271 (7-(6-fluoropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 272 (7-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 273 (7-(2,6-difluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 279 (7-(3-chloro-5-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 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 Example 281 (7-(6-chloro-5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 282 (7-(2,6-dichloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 283 (7-(5-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 284 (7-(5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 285. 3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile Example 288 (7-(5,6-difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl](piperidin-1-yl)methanone Example 289 (7-(5-chloro-6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 290. 2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile Example 291. 3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile Example 292 (7-(4-bromophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 293. 5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidine-2-carbonitrile Example 294. [7-(2-hydroxypyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone Example 298 (7-(5-chloro-2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 312. 3-nitro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile Example 313 (7-(6-bromopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 314. (7-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 315. (7-(6-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 318. (7-(5-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0062] 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, Regarding 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, and 318, the compounds were obtained using compound 1-2 and the corresponding compounds in the same synthetic method as in steps 1-3 in Example 1. The structures and spectral data are shown in Table 1 below. [Table 1-1] [Table 1-2] [Table 1-3] [Table 1-4] [Table 1-5] [Table 1-6] [Table 1-7] [Table 1-8] [Table 1-9] [Table 1-10] [Table 1-11] [Table 1-12] [Table 1-13]

[0063] Example 7 (7-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] Compound 5 (0.331 g, 0.94 mmol) was dissolved in methanol (16.5 mL), and palladium on carbon (0.025 g, 0.24 mmol) was added. The reaction solution was charged with hydrogen gas and stirred for 12 hours. After the reaction was completed, 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 brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to obtain the target compound 7 (0.297 g, 95%). 1 H NMR(400MHz,DMSO-d6)δ(ppm): 8.21(s, 1H),7.83(dd,J=8.9,1.4Hz,1H),7.47(dd,J=8.9,7.0Hz,1H),7.17(d,J=7.8Hz,1H),7.09(t,J=2.0Hz,1H),7.05(dd,J=7.1 ,1.4Hz,1H),6.99-6.94(m,1H),6.75-6.68(m,1H),5.27(s,2H),3.62(t,J=5.4Hz,4H),1.65(d,J=5.2Hz,2H),1.57(s,4H). MS(ESI,LR)Calc. for C 19 H 21 NO[M+H] + :321.2,found:321.2.

[0064] Example 9 (7-(5-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 14 (7-(4-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 17 (7-(6-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0065] Examples 9, 14, and 17 were obtained using Compound 1-2 and the corresponding compounds by sequentially following the synthesis method of steps 1-3 in Example 1 and the synthesis method in Example 7. The structures and spectral data are shown in Table 2 below. [Table 2]

[0066] Example 26 (7-(3-(morpholine-4-carbonyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] Step 26-1: Using compound 1-2 and 3-boronobenzoic acid, the target compound 26-1 was obtained by the same synthetic method as in step 1-3 of Example 1.

[0067] Step 26-2: Using compound 26-1 and morpholine, the target compound 26 was obtained by the same synthetic method as in step 1-2 in Example 1. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.03-7.92(m,3H),7.65-7.54(m,2H),7.38(dd,J=8 .9,7.0Hz,1H),6.98(dd,J=7.0,1.4Hz,1H),3.78-3.60(m,12H),1.74-1.66(m,6H). MS(ESI,LR)Calc. for C 24 H 27 N 4 O 3 [M+H] + :419.2,found:419.2.

[0068] Example 27: N-methyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 28: N-isopropyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 29. Azetidin-1-yl(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone Example 30: N-(2-methoxyethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 31: N-(2-(dimethylamino)ethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 32: N-(cyclopropylmethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 33: N-(1-methylpiperidin-4-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 35. tert-butyl 4-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoyl)piperazine-1-carboxylate Example 36: N-(2-cyanoethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 37. 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide Example 38. 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide

[0069] Examples 27, 28, 29, 30, 31, 32, 33, 35, 36, 37, and 38 were obtained using compound 26-1 and the corresponding compounds by the same synthetic method as in steps 1-2 in Example 1. The structures and spectral data are shown in Table 3 below. [Table 3-1] [Table 3-2] [Table 3-3]

[0070] Example 34. Piperazin-1-yl(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone [ka] Compound 35 (0.1 g, 0.19 mmol) was dissolved in dichloromethane (1 mL) and stirred at 0°C for 10 minutes. 4N hydrochloric acid (0.48 mL) dissolved in 1,4-dioxin was added and stirred at room temperature for 16 hours. After completion of the reaction, the reaction mixture was concentrated and separated using column chromatography to obtain target compound 34 (36 mg, 44%). 1H NMR(400MHz,DMSO-d6)δ(ppm):8.25(s,1H),8.07(d,J=1.7Hz,1H),8.01(dt,J=7.5,1. 7Hz,1H),7.91(dd,J=8.9,1.4Hz,1H),7.71-7.60(m,2H),7.54(dd,J=8.9,7.0Hz,1H), 7.23(dd,J=7.0,1.4Hz,1H),3.76(s,4H),3.62(t,J=5.5Hz,4H),3.20(t,J=5.1Hz,4H),1.66(d,J=5.2Hz,2H),1.57(s,4H). MS(ESI,LR)Calc. for C 24 H 28 NO2[M+H] + :418.2,found:418.2.

[0071] Example 39 (7-(5-(morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] 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 chemical compound 39-1 was obtained in the same synthetic method as in Step 1-3 of Example 1.

[0072] Step 39-2: Using compound 39-1 and morpholine, the target compound 39 was obtained by the same synthetic method as in Step 1-2 in Example 1. 1H NMR(400MHz,DMSO-d6)δ(ppm):9.15(d,J=2.2Hz,1H),8.77(d,J=2.0Hz,1H),8.48(t,J=2.1Hz, 1H),8.27(s,1H),7.95(dd,J=8.9,1.3Hz,1H),7.55(dd,J=8.9,7.0Hz,1H),7.36(dd,J=7.1,1.4 Hz,1H),3.67(s,4H),3.63(t,J=5.4Hz,6H),3.47(s,2H),1.66(d,J=5.7Hz,2H),1.57(d,J=7.4Hz,4H). MS(ESI,LR)Calc. for C 23 H 26 N5O3[M+H] + :420.2,found:420.2.

[0073] Example 40. N-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide Example 41. Azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone Example 42 (3-hydroxyazetidin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone Example 43 (7-(5-(2-azaspiro[3.3]heptane-2-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 44 (3,3-difluoroazetidin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone Example 45. N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide Example 46. N-(cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide Example 47. N-(1-methylpiperidin-4-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide Example 51. N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide Example 52. N-(cyanomethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide Example 53. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)nicotinamide Example 54. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)nicotinamide Example 55. N-(isoxazol-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide Example 56. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridazin-4-yl)nicotinamide Example 57. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(thiazol-5-ylmethyl)nicotinamide Example 192 (3-fluoroazetidin-1-yl)(5-(3-piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone Example 193. N-(1-methyl-1H-pyrazol-3-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide Example 201. N-methylsulfonyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide Example 203. 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazin-2-one Example 204. 4-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazine-2,6-dione Example 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 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

[0074] Examples 40, 41, 42, 43, 44, 45, 46, 47, 51, 52, 53, 54, 55, 56, 57, 192, 193, 201, 203, 204, 225, and 226 were obtained using compound 39-1 and the corresponding compounds by the same synthetic method as in steps 1 and 2 of Example 1. The structures and spectral data are shown in Table 4 below. [Table 4-1] [Table 4-2] [Table 4-3] [Table 4-4] [Table 4-5]

[0075] Example 48. Piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone Example 200. N-(azetidin-3-yl)-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]nicotinamide

[0076] The target compound was obtained using compound 39-1 and the corresponding compound in the same manner as in steps 1-2 of Example 1 and the method used to synthesize Example 34. The structure and spectral data are shown in Table 5 below. [Table 5]

[0077] Example 49 (4-methylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone [ka] Compound 48 (50 mg, 0.12 mmol) was dissolved in ethyl alcohol (0.6 mL) and water (0.6 mL), and then 37% formaldehyde (17.8 μL, 0.24 mmol) was added and 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 then purified by column chromatography to obtain the target compound 49 (30 mg, 57%). 1 H NMR (400MHz, DMSO-d6)δ(ppm):9.14(d,J=2.1Hz,1H),8.74(d,J=2.0Hz,1H),8. 45(t,J=2.1Hz,1H),8.27(s,1H),7.94(dd,J=8.9,1.3Hz,1H),7.55(dd,J=8.9, 7.0Hz,1H),7.36(dd,J=7.0,1.4Hz,1H),3.64(q,J=8.5Hz,6H),3.44(s,2H),2. 37(d,J=19.9Hz,4H),2.21(s,3H),1.65(d,J=5.5Hz,2H),1.57(d,J=7.2Hz,4H). MS(ESI,LR)Calc. for C 24 H 29 N6O2[M+H] + :433.2,found:433.1.

[0078] Example 202. N-(1-methylazetidin-3-yl)-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide [ka] Compound 200 and the corresponding compound were used in the same synthesis method as in Example 49 to obtain target compound 202. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.68-9.54(m,1H),9.26(t,J=2.4Hz,1H),9.18(d,J= 5.6Hz,1H),8.81(t,J=2.0Hz,1H),7.98-7.93(m,1H),7.56(dd,J=8.9,7.0Hz,1H),7. 38(dd,J=7.1,2.9Hz,1H),4.49(s,1H),4.16(dt,J=18.1,8.5Hz,2H),3.62(t,J=5.4H z,4H),2.89(d,J=5.5Hz,4H),2.73(s,1H),1.65(q,J=5.6Hz,2H),1.60-1.51(m,4H). MS(ESI,LR)Calc. for C 23 H 27 N6O2[M+H] + :419.1, found:419.1.

[0079] Example 50 (4-isopropylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone [ka] Compound 48 and acetone were used to obtain target compound 50 by the synthesis method used in Example 49. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.14(d,J=2.2Hz,1H),8.75(d,J=2.1Hz,1H),8.45(t, J=2.1Hz,1H),8.27(s,1H),7.94(dd,J=8.9,1.3Hz,1H),7.55(dd,J=8.9,7.1Hz,1H), 7.36(dd,J=7.0,1.3Hz,1H),3.63(t,J=5.5Hz,6H),3.42(s,2H),2.70(p,J=6.5Hz,1H ),2.49(d,J=12.9Hz,4H),1.65(d,J=5.1Hz,2H),1.57(s,4H),0.98(d,J=6.5Hz,6H). MS(ESI,LR)Calc. for C 26 H 33 N6O2[M+H] + :461.3,found:461.2.

[0080] Example 58. N-methyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 59: N,N-dimethyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 60. N-isopropyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 61. Azetidin-1-yl(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone Example 62: N-(2-methoxyethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 63. N-(2-(dimethylamino)ethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 64: N-(cyclopropylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 65. N-(1-methylpiperidin-4-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 69: N-(2-cyanoethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 70: N-(cyanomethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide Example 71. 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide Example 72. 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide Example 73. N-(isoxazol-3-ylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0081] Examples 58, 59, 60, 61, 62, 63, 64, 65, 69, 70, 71, 72, and 73 were obtained using compound 10 and the corresponding compounds by the same synthetic method as in steps 1 and 2 in Example 1. The structures and spectral data are shown in Table 6 below. [Table 6-1] [Table 6-2] [Table 6-3]

[0082] Example 66. Piperazin-1-yl(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone [ka] Compound 10 and 1-Boc-piperazine were used in the same synthesis method as in steps 1-2 of Example 1 and the synthesis method of Example 34, to obtain the target compound 66. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.24(s,1H),8.03(d,J=8.1Hz,2H),7.90(dd,J=8.9,1.3Hz,1H),7.65(d,J=8.3Hz,2H),7.53(dd, J=8.9,7.0Hz,1H),7.22(dd,J=7.1,1.4Hz,1H),3.62(t,J=5.4Hz,8H),3.18(s,4H),1.66(d,J=5.8Hz,2H),1.57(d,J=7.4Hz,4H). MS(ESI,LR)Calc. for C 24 H 28 NO2[M+H] + :418.2,found:418.1.

[0083] Example 67 (4-methylpiperazin-1-yl)(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone Example 68 (4-isopropylpiperazin-1-yl)(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0084] Examples 67 and 68 were obtained using Compound 66 and the corresponding compounds by the synthesis method used in Example 49. The structures and spectral data are shown in Table 7 below. [Table 7]

[0085] Example 74 (7-(6-(morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] The target compound 74 was obtained by the synthesis method used in Example 39 using compound 1-2 and methyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylate. 1H NMR(400MHz,DMSO-d6)δ(ppm):9.15(d,J=2.1Hz,1H),8.77(d,J=2.0Hz,1H),8.48(t,J=2.1Hz,1H),8.27(s,1H),7.95(dd,J=9.0,1.3Hz,1H ),7.55(dd,J=8.9,7.0Hz,1H),7.36(dd,J=7.0,1.4Hz,1H),3.64(q,J=9.3Hz,10H),3.46(s,2H),1.72-1.61(m,2H),1.58(t,J=6.5Hz,4H). MS(ESI,LR)Calc. for C 23 H 26 N5O3[M+H] + :420.2,found:420.1.

[0086] Example 75. N-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 76. N-isopropyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 77. Azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone Example 78. N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 79: N-(2-(dimethylamino)ethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 80. N-(cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 81. N-(1-methylpiperidin-4-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 85. N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 86. N-(cyanomethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 87. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)picolinamide Example 88. 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)picolinamide Example 89. N-(isoxazol-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide Example 213 (3-fluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone Example 214. 2-Azaspiro[3.3]heptan-2-yl-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone Example 237 (3,3-difluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone

[0087] Examples 75, 76, 77, 78, 79, 80, 81, 85, 86, 87, 88, 89, 213, 214, and 237 were obtained using compound 74-1 and the corresponding compounds by the same synthetic method as in steps 1-2 in Example 1. The structures and spectral data are shown in Table 8 below. [Table 8-1] [Table 8-2] [Table 8-3]

[0088] Example 82. Piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone [ka] Using compound 74-1 and 1-Boc-piperazine, the target compound 82 was obtained by the same synthesis method as in step 1-2 of Example 1 and the method used to synthesize Example 34, in that order. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.13(d,J=2.1Hz,1H),9.02(s,2H),8.56(dd,J=8.1,2.2Hz,1H ),8.27(s,1H),7.95(dd,J=8.9,1.3Hz,1H),7.87(d,J=8.2Hz,1H),7.57(dd,J=8.9,7.1Hz,1H ),7.35(dd,J=7.1,1.4Hz,1H),3.91(d,J=5.6Hz,2H),3.78(d,J=6.2Hz,2H),3.63(t,J=5.4Hz ,4H),3.21(d,J=6.3Hz,2H),3.18-3.08(m,2H),1.66(q,J=5.6Hz,2H),1.58(q,J=5.5Hz,4H). MS(ESI,LR)Calc. for C 23 H 27 N6O2[M+H] + :419.2,found:419.1.

[0089] Example 83 (4-methylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone Example 84 (4-isopropylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0090] Examples 83 and 84 were obtained using compound 74-1 and the corresponding compounds by the synthesis method used in Example 49. The structures and spectral data are shown in Table 9 below. [Table 9]

[0091] Example 243. 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid [ka]

[0092] 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 manner as in Step 1-3 in Example 1.

[0093] Step 243-2: Compound 243-1 (19 mg, 49 μM) was dissolved in tetrahydrofuran (1 mL), followed by the addition of 1N sodium hydroxide (0.3 mL) and stirring at 0 °C for 2 hours. After the reaction was complete, water (3 mL) was added to the reaction solution and washed with dichloromethane. The aqueous layer was acidified with 1N hydrochloric acid to a pH of 2 and then extracted with dichloromethane (5 mL × 3). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to give the target compound 243 (12 mg, 66%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):13.82(s,1H),9.07(d,J=1.6Hz,1H),8.57(dd,J=11.5,1.7Hz,1H),8.31(s,1H),7.98(dd,J=8.9,1.3H) z,1H),7.57(dd,J=8.9,7.1Hz,1H),7.46(dd,J=7.1,1.4Hz,1H),3.63(t,J=5.4Hz,4H),1.65(q,J=5.6Hz,2H),1.57(q,J=5.7Hz,4H). MS(ESI,LR)Calc. for C 19 H 18 FN4O3[M+H] + :369.1,found:369.1.

[0094] Example 248. [7-[6-(azetidine-1-carbonyl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] Using compound 243 and azetidine, the target compound 248 was obtained by the same synthetic method as in step 1-2 of Example 1. 1H NMR(400MHz,DMSO-d6)δ(ppm):9.02(t,J=1.5Hz,1H),8.53(dd,J=11.2,1.7Hz, 1H),8.30(s,1H),7.97(dd,J=8.9,1.4Hz,1H),7.56(dd,J=8.9,7.1Hz,1H),7.43 (dd,J=7.0,1.3Hz,1H),4.28(t,J=7.7Hz,2H),4.13(t,J=7.8Hz,2H),3.63(t,J= 5.4Hz, 4H), 2.32 (p, J = 7.7Hz, 2H), 1.66 (d, J = 5.2Hz, 2H), 1.57 (d, J = 6.7Hz, 4H). MS(ESI,LR)Calc. for C 22 H 23 FN5O2[M+H] + :408.2,found:408.1.

[0095] Example 249. [7-[5-fluoro-6-(morpholine-4-carbonyl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone Example 250. 3-fluoro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide

[0096] In Examples 249 and 250, the target compounds were obtained using compound 243 and the corresponding compounds in the same synthetic method as in steps 1 and 2 in Example 1. The structures and spectral data are shown in Table 10 below. [Table 10]

[0097] Example 277. [7-[2-(azetidine-1-carbonyl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] Compound 277-1 was obtained using compound 1-2 and (2-(methoxycarbonyl)pyrimidin-5-yl)boronic acid in the same synthetic method as in step 1-3 of Example 1, and then the target compound 277 was obtained using azetidine in the same synthetic method as in step 1-2 of Example 1. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.51(s, 2H),8.31(s,1H),7.98(dd,J=8.9,1.4Hz,1H),7.58(dd,J=8.9,7.0Hz,1H),7.48(dd,J=7.1,1.4Hz,1H),4.48(t,J=7.7 Hz,2H),4.14(t,J=7.7Hz,2H),3.63(t,J=5.4Hz,4H),2.39-2.27(m,2H),1.66(d,J=5.4Hz,2H),1.57(d,J=6.9Hz,4H). MS(ESI,LR)Calc. for C 21 H 23 N6O2[M+H] + :391.2,found:391.1.

[0098] Example 258. 3-chloro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid [ka] An intermediate was obtained using (5-chloro-6-(methoxycarbonyl)pyridin-3-yl)boronic acid in the same synthetic method as in step 1-3 of Example 1, and then the target compound 258 was obtained in the same synthetic method as in step 243-2 of Example 243. 1 H NMR(400MHz,DMSO-d6)δ(ppm):14.07(s,1H),9.08(d,J=1.8Hz,1H),8.71(d,J=1.9Hz,1H),8.30(s,1H),7.97(dd,J=8.9,1.4Hz ,1H),7.56(dd,J=8.9,7.1Hz,1H),7.43(dd,J=7.0,1.4Hz,1H),3.63(t,J=5.4Hz,4H),1.73-1.62(m,2H),1.57(d,J=7.4Hz,4H). MS(ESI,LR)Calc. for C 19 H 18 ClN4O3[M+H] + :385.1,found:385.1.

[0099] Example 262. 3-chloro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide Example 286. [7-[6-(azetidine-1-carbonyl)-5-chloro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0100] Examples 262 and 286 were obtained using compound 258 and the corresponding compounds by the same synthetic method as in steps 1 and 2 in Example 1. The structures and spectral data are shown in Table 11 below. [Table 11] MS(ESI,LR) Calc. for C 22 H 23 ClNO2[M+H] + :424.1,found:424.1.

[0101] Example 90. N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)furan-2-carboxamide [ka] Compound 90-1 was obtained using compound 1-2 and methyl(5-methoxycarbonyl-2-furyl)boronic acid by the synthesis method used in Example 39, and then target compound 90 was obtained using 3-aminopropanenitrile by the same synthesis method as in step 1-2 in Example 1. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.11(t,J=5.9Hz,1H),8.42(s,1H),8.05-7.91(m,3H),7.64(dd,J=8.8,7.3Hz,1H),7.39(d,J= 3.6Hz,1H), 3.64(t,J=5.4Hz,4H),3.56(q,J=6.3Hz,2H),2.83(t,J=6.5Hz,2H),1.66(d,J=4.9Hz,2H),1.58(d,J=6.0Hz,4H). MS(ESI,LR)Calc. for C 21 H 22 N5O3[M+H] + :392.2,found:392.1.

[0102] Example 230 (3-hydroxyiminoazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone [ka] Using compound 39-1 and azetidin-3-one, an intermediate was obtained by a synthetic method similar to that in step 1-2 in Example 1, and then the target compound 230 was obtained by a synthetic method similar to that in step 236-2 in Example 236. 1 H NMR(400MHz,DMSO-d6)δ(ppm):11.07(d,J=12.6Hz,1H),9.22(d,J=2.2Hz,1H),9.00(d,J=2.1Hz,1H),8.68(s,1H),8.27(d,J=6.5Hz,1H),7.95(d,J= 8.9Hz,1H),7.56(dd,J=8.9,7.0Hz,1H),7.37(d,J=7.0Hz,1H),5.13(s,2H ),4.79(d,J=17.8Hz,2H),3.63(s,4H),1.65(d,J=6.1Hz,2H),1.57(s,4H). MS(ESI,LR)Calc. for C 22 H 23 N6O3[M+H] + :419.2,found:419.1.

[0103] Example 91. 3-Methoxy-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide Example 93. 1-methyl-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide Example 94. N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropanecarboxamide Example 95. N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide Example 96. N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide Examples 91, 93, 94, 95, and 96 were obtained using compound 7 and the corresponding compounds by the same synthetic method as in steps 1 and 2 in Example 1. The structures and spectral data are shown in Table 12 below. [Table 12]

[0104] Example 92. 1-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)urea [ka] 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 the reaction was completed, the temperature was lowered using ice water, and the precipitated solid was collected by filtration. The target compound 92 (35.6 mg, 45%) was obtained by recrystallization using boiling water. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.74(s, 1H),8.22(s,1H),7.95(d,J=2.1Hz,1H),7.86(dd,J=8.9,1.3Hz,1H),7.60-7.54(m,1H),7.50(dd,J=8.9,7.0Hz,1H),7 .42-7.37(m,2H),7.11(dd,J=7.0,1.4Hz,1H),5.91(s,2H),3.62(t,J=5.3Hz,4H),1.65(d,J=7.7Hz,2H),1.57(s,4H). MS(ESI,LR)Calc. for C 20 H 22 NO2[M+H] + :364.2,found:364.2.

[0105] Example 97. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)acetamide Example 98. 3-methoxy-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide Example 99. 1-methyl-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide Example 100. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropanecarboxamide Example 101. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide Example 102. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexanecarboxamide Example 274. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide

[0106] Examples 97, 98, 99, 100, 101, 102, and 274 were obtained using compound 14 and the corresponding compounds by the same synthetic method as steps 1 and 2 in Example 1. The structures and spectral data are shown in Table 13 below. [Table 13-1] [Table 13-2]

[0107] Example 196. 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide Example 197. 3-Methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)propenamide Example 198. 2-oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)piperidine-4-carboxamide Example 326. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide Example 327. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyridin-3-yl)acetamide Example 333. 1,2-dimethyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1H-imidazole-5-carboxamide Example 334. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)pyrimidine-5-carboxamide Example 335. 5-fluoro-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide 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 Example 389. 2-phenyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide Example 402. 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide Example 403. N-(5-(3-piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyrimidin-5-yl)acetamide Example 406. 2-(4-chlorophenoxy)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0108] Examples 196, 197, 198, 326, 327, 333, 334, 335, 388, 389, 402, 403, and 406 were obtained using compound 9 and the corresponding compounds in the same synthetic method as in steps 1 and 2 of Example 1. The structures and spectral data are shown in Table 4 below. [Table 14-1] [Table 14-2] [Table 14-3]

[0109] Example 103. 3-Methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)propanamide [ka] 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, which was then 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 brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The target compound 103 (27.2 mg, 43%) was obtained by column chromatography. 1 H NMR(400MHz,DMSO-d6)δ(ppm):10.75(s, 1H),8.89(d,J=2.4Hz,1H),8.40(dd,J=8.8,2.4Hz,1H),8.28-8.25(m,1H),7.89(dd,J=8.8,1.3Hz,1H),7.52(dd,J=8.9,7.1Hz,1H),7.27 (dd,J=7.1,1.4Hz,1H),5.75(s,1H),3.64(dt,J=10.7,5.7Hz,6H),3.26(s,3H),2.70(t,J=6.2Hz,2H),1.65(d,J=5.6Hz,2H),1.57(s,4H). MS(ESI,LR)Calc. for C 23 H 28 N5O3[M+H] + :408.2,found:408.1.

[0110] Example 104. 2-(dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide [ka] 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 the mixture was stirred for 1 hour. Compound 17 (0.1 g, 0.31 mmol) was added to the reaction solution, and the mixture was stirred for 3 hours. After the reaction was completed, 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 104 (36.3 mg, 29%). [HOBt (Hydroxybenzotriazole), EDCI (1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide)] 1 H NMR(400MHz,DMSO-d6)δ(ppm):10.17(s, 1H),8.88(d,J=2.4Hz,1H),8.43(dd,J=8.7,2.4Hz,1H),8.30-8.22(m,2H),7.89(dd,J=8.9,1.4Hz,1H),7.52(dd,J=8.9,7.0Hz, 1H),7.27(dd,J=7.1,1.4Hz,1H),3.62(t,J=5.4Hz,4H),3.20(s,2H),2.33(s,6H),1.65(d,J=7.6Hz,2H),1.57(q,J=5.8Hz,4H). MS(ESI,LR)Calc. for C 22 H 27 N6O2[M+H] + :407.2,found:407.1.

[0111] Example 105. 2-oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)piperidine-4-carboxamide [ka] 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), followed by addition of triethylamine (86 μL, 0.62 mmol) and stirring for 1 hour. Compound 17 (0.1 mg, 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 then separated using column chromatography to obtain the target compound 105 (29.8 mg, 22%). 1 H NMR (400MHz, DMSO-d6)δ(ppm):10.87(s, 1H),8.90(d,J=2.4Hz,1H),8.41(dd,J=8.8,2.4Hz,1H),8.26(d,J=7.7Hz,2H),7.91-7.86(m,1H),7.52(t,J=7.9Hz,2H),7.27( d,J=7.0Hz,1H),3.62(t,J=5.5Hz,4H),3.24-3.00(m,4H),2.35(d,J=7.7Hz,2H),2.05-1.96(m,1H),1.65(s,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 24 H 27 N6O3[M+H] + : 447.2,found:447.1.

[0112] Example 106. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide [ka] The target compound 106 was obtained using compound 17 and 2-(3-pyridyl)acetic acid by the synthesis method used in Example 105. 1 H NMR(400MHz,DMSO-d6)δ(ppm):11.10(s,1H),8.91(dd,J=2.4,0.9Hz,1H),8.56(d,J=2.3Hz,1H),8.4 8(dd,J=4.8,1.7Hz,1H),8.40(dd,J=8.7,2.4Hz,1H),8.26(s,1H),8.21(d,J=8.7Hz,1H),7.89(dd,J= 8.8,1.4Hz,1H),7.78(dt,J=7.8,2.1Hz,1H),7.52(dd,J=8.9,7.1Hz,1H),7.42-7.34(m,1H),7.27(dd ,J=7.1,1.3Hz,1H),3.85(s,2H),3.62(t,J=5.4Hz,4H),1.65(d,J=5.6Hz,2H),1.56(d,J=7.1Hz,4H). MS(ESI,LR) Calc. for C 25 H 25 N6O2[M+H] + :441.2,found:441.1.

[0113] Example 407. N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl-2-pyrimidin-5-yl-acetamide Example 408. N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-2-[6-(trifluoromethyl)-3-pyridyl]acetamide Example 409. 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide Example 410. 2-(4-chlorophenoxy)-N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]acetamide

[0114] Examples 407, 408, 409, and 410 were obtained using compound 17 and the corresponding compounds by the same synthetic method as in steps 1 and 2 in Example 1. The structures and spectral data are shown in Table 15 below. [Table 15]

[0115] Example 278. N-(2,6-difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide [ka] Step 278-1: Using 4-bromo-2,6-difluoroaniline and 2-(3-pyridyl)acetic acid, the target compound 278-1 was obtained in the same synthetic manner as in Step 1-2 of Example 1.

[0116] Step 278-1 [Step 278-2]: Using compound 278-1, the target compound 278-2 was obtained by the same synthetic method as in Step 351-1 in Example 351.

[0117] Step 278-1 [Step 278-3]: Using compound 278-2, the target compound 278 was obtained by the same synthetic method as in Step 159-3 in Example 159. 1 H NMR(400MHz,DMSO-d6)δ(ppm):10.21(s,1H),8.56(d,J=2.3Hz,1H),8.49(dd,J=4.8,1 .7Hz,1H),8.27(s,1H),7.92(dd,J=8.9,1.3Hz,1H),7.84(d,J=8.9Hz,2H),7.82-7.72( m,1H),7.52(dd,J=8.9,7.1Hz,1H),7.40(dd,J=7.9,4.8Hz,1H),7.32(dd,J=7.1,1.3Hz ,1H),3.82(s,2H),3.62(t,J=5.4Hz,4H),1.65(d,J=5.6Hz,2H),1.56(d,J=6.9Hz,4H). MS(ESI,LR) Calc. for C 26 H 24 F2N5O2[M+H] + :476.2,found: 476.1.

[0118] Example 107 (7-(6-((3-methoxypropyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] 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 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 brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography to give target compound 107 (0.059 g, 49%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.55(d,J=2.4Hz,1H),8.22(s,1H),8.02(dd,J=8.9,2.5H z,1H),7.78(dd,J=8.9,1.4Hz,1H),7.46(dd,J=8.9,7.1Hz,1H),7.11(dd,J=7.2,1.4Hz, 1H),6.59(d,J=8.9Hz,1H),3.61(t,J=5.4Hz,4H),3.42(t,J=6.3Hz,2H),3.38(d,J=6.7H z,2H),3.26(s,3H),1.80(p,J=6.6Hz,2H),1.65(d,J=6.0Hz,2H),1.56(d,J=7.1Hz,4H). MS(ESI,LR) Calc. for C 22 H 28 NO2[M+H] + :394.2,found:394.2.

[0119] Example 108 (7-(6-morpholinopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 109 (7-(6-(isopropylamino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 110. Piperidin-1-yl(7-(6-(piperidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone Example 111 (7-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 206 (7-(6-(azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 208 (7-(6-(3-fluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 209 (7-(6-(3,3-difluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 210 (7-(6-(3-hydroxyazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 215 (7-(6-(2-azabicyclo[2.2.1]heptan-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 216 (7-(6-(2-azabicyclo[2.2.2]octaN-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 217 (7-(6-(7-azabicyclo[2.2.1]heptan-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 218 (7-(6-(3-(dimethylamino)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 219. Methyl 1-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)azetidine-3-carboxylate Example 220 (7-(6-(2-azaspiro[3.3]heptan-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 221 (7-(6-(3-(hydroxymethyl)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone 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 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 Example 332. Piperidin-1-yl(7-(6-((2-pyridin-3-yl)ethyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone Example 344 (7-(6-(4-amino-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0120] Examples 108, 109, 110, 111, 206, 208, 209, 210, 215, 216, 217, 218, 219, 220, 221, 222, 223, 332, and 344 were obtained using compound 19 and the corresponding compounds by the synthesis method in Example 107. The structures and spectral data are shown in Table 16 below. [Table 16-1] [Table 16-2] [Table 16-3] [Table 16-4]

[0121] Example 287. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide [ka] 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 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 brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to give target compound 287 (39.4 g, 82%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):11.36(s,1H),9.19(d,J=2.3Hz,1H),8.98(d,J=2. 3Hz,1H),8.79(dd,J=4.8,1.7Hz,1H),8.50(dd,J=8.8,2.4Hz,1H),8.46-8.35(m, 2H),8.28(s,1H),7.91(dd,J=8.8,1.4Hz,1H),7.62-7.50(m,2H),7.32(dd,J=7.1 ,1.4Hz,1H),3.63(t,J=5.4Hz,4H),1.66(d,J=6.0Hz,2H),1.58(d,J=7.4Hz,4H). MS(ESI,LR) Calc. for C 24 H 23 N6O2[M+H] + :427.2,found:427.1.

[0122] Example 316. 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one Example 355 (7-(6-(4-nitro-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0123] Examples 316 and 355 were obtained using Compound 19 and the corresponding compounds by the same synthetic method as in Example 287. The structures and spectral data are shown in Table 17 below. [Table 17]

[0124] Example 301. N-(3-chloro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide 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

[0125] Examples 301 and 311 were obtained using Compound 289 and the corresponding compounds by the synthesis method in Example 287. The structures and spectral data are shown in Table 18 below. [Table 18]

[0126] Example 323. 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one 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

[0127] Examples 323 and 362 were obtained using Compound 288 and the corresponding compounds by the synthesis method in Example 287. The structures and spectral data are shown in Table 19 below. [Table 19]

[0128] Example 308. 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-2-yl)oxazolidin-2-one [ka] The target compound 308 was obtained by the synthesis method in Example 287 using compound 267 and oxazolidin-2-one. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.30(s, 2H),8.27(s,1H),7.93(dd,J=8.9,1.4Hz,1H),7.55(dd,J=8.9,7.0Hz,1H),7.38(dd,J=7.1,1.4Hz,1H),4. 48(t,J=7.9Hz,2H),4.27(t,J=7.9Hz,2H),3.62(d,J=5.3Hz,4H),1.73-1.63(m,2H),1.58(d,J=7.2Hz,4H). MS(ESI,LR) Calc. for C 20 H 21 N6O3[M+H] + :393.2,found: 393.1.

[0129] Example 257 (7-(2-(3-fluoroazetidin-1-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] An intermediate was obtained using compound 1-2 and (2-fluoro-4-pyridyl)boronic acid in the same synthetic method as in step 1-3 in Example 1, and then target compound 257 was obtained using azetidine in the synthetic method in Example 107. 1H NMR(400MHz,DMSO-d6)δ(ppm):8.65(d,J=2.3Hz,1H),8.23(s,1H),8.19(dd,J=8.7,2.4Hz,1H),7. 82(dd,J=8.9,1.4Hz,1H),7.48(dd,J=8.9,7.1Hz,1H),7.16(dd,J=7.1,1.4Hz,1H),6.61(d,J=8.8H z,1H),5.56(ddt,J=57.4,5.9,2.9Hz,1H),4.39(dddd,J=21.3,10.3,5.9,1.5Hz,2H),4.12(dddd, J=24.5,10.4,3.2,1.5Hz,2H),3.62(t,J=5.4Hz,4H),1.65(d,J=5.4Hz,2H),1.56(d,J=7.6Hz,4H). MS(ESI,LR) Calc. for C 21 H 23 FN5O[M+H] + :380.2,found: 380.1.

[0130] Example 112. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanesulfonamide [ka] Compound 17 (0.1 g, 0.31 mmol) and triethylamine (97 μL, 0.7 mmol) were dissolved in dichloromethane (5 mL). The temperature was then adjusted to 0 °C using ice water, and methanesulfonyl chloride (52 μL, 0.7 mmol) was added dropwise. The temperature was then raised to room temperature and 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 (30 mL), and brine (30 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The target compound 112 (29 mg, 24%) was obtained by column chromatography. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.80(d,J=2.4Hz,1H),8.33(dd,J=8.7,2.4Hz,1H),8.25(s,1H),7.88(dd,J=8.9,1.3Hz,1H),7.51(dd,J=8.9,7 .1Hz,1H),7.24(dd,J=7.0,1.4Hz,1H),7.12(d,J=8.7Hz,1H),3.62(t,J=5.4Hz,4H),3.36(s,3H),1.65(d,J=7.5Hz,2H),1.56(d,J=7.6Hz,4H). MS(ESI,LR) Calc. for C 20 H 22 N5O4S[M+H] + :400.1,found:400.0.

[0131] Example 113 (7-(3-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] 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 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%). 1H NMR(400MHz,DMSO-d6)δ(ppm):8.51(t,J=1.7Hz,1H),8.25(s,1H),8.12(dt,J=7.7,1.4Hz,1H),7.89(dd,J=8.9,1.3Hz,1H),7.78(dt,J =7.7,1.5Hz,1H),7.55(dt,J=10.8,8.3Hz,2H),7.20(dd,J=7.0,1.3Hz,1H),3.64(t,J=5.4Hz,4H),1.65(d,J=7.4Hz,2H),1.58(s,4H). MS(ESI,LR) Calc. for C 20 H 20 NO[M+H] + :374.2,found:374.2.

[0132] Example 114 (7-(4-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0133] [ka] Compound 15 and the corresponding compound were used to obtain target compound 114 by the synthesis method in Example 113. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.26(s, 1H),8.14(d,J=8.1Hz,2H),7.97(d,J=9.2Hz,2H),7.90-7.83(m,1H),7.52(dd,J=8.9 ,7.1Hz,1H),7.22(d,J=7.0Hz,1H),3.63(t,J=5.4Hz,4H),1.65(s,2H),1.58(s,4H). MS(ESI,LR) Calc. for C 20 H 20 NO[M+H] + :374.2,found:374.2.

[0134] Example 115. 3-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one [ka] Step 115-1: Compound 6 (0.15 g, 0.45 mmol) was dissolved in ethyl alcohol (6.5 mL), and then hydroxylamine (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 target compound 115-1 (0.079 g, 24%).

[0135] 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. Triphosgene (0.065 g, 0.22 mmol) dissolved in tetrahydrofuran (5 mL) was slowly added to the reaction solution, which was then stirred at room temperature for 30 minutes. The temperature was then raised to 80°C and the mixture was stirred for 1 hour. After completion of the reaction, the reaction solution was concentrated and separated using column chromatography to obtain the target compound 115 (0.093 g, 43%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.36(d,J=2.0Hz,1H),8.26(s,1H),8.09(d,J=7.8Hz,1H),7.94(dd,J=15.0,8.4Hz,2H),7.71(t, J=7.5Hz,1H),7.55(dd,J=8.9,7.0Hz,1H),7.24(d,J=6.7Hz,1H),6.53(s,1H),3.63(t,J=5.4Hz,3H),1.65(s,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 21 H 20 N5O3[M+H] + :390.2,found:390.1.

[0136] Example 116. 3-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one Example 117. 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-1,2,4-oxadiazol-5(4H)-one Example 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 Example 275. 3-[2-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one Example 295. 3-[3-fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-4H-1,2,4-oxadiazol-5-one Example 297. 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1,2,4-oxadiazol-5-(4H)-one Example 299. 3-(3-fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one 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 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 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 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

[0137] Examples 116, 117, 247, 275, 295, 297, 299, 304, 321, 329, and 331 were obtained from compounds 1-2 and the corresponding compounds by sequentially following the synthesis methods in steps 1-3 of Example 1 and the synthesis method of Example 115. The structures and spectral data are shown in Table 20 below. [Table 20-1] [Table 20-2]

[0138] Example 118 (7-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] Compound 116-1 (0.014 g, 0.038 mmol) was dissolved in pyridine (2 mL), and then 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 brine (10 mL × 2). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to obtain the target compound 118 (5.4 mg, 36%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.27(s,1H),8.20-8.11(m,4H),7.92(dd,J=8.8,1.3Hz,1H),7.54(dd,J =8.9,7.0Hz,1H),7.28(d,J=7.0Hz,1H),3.63(t,J=5.5Hz,4H),2.71(s,3H),1.65(s,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 22 H 22 NO2[M+H] + :388.2,found:388.1.

[0139] 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 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 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 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 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 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 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 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 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

[0140] For Examples 263, 276, 296, 303, 317, 319, 322, 328, and 330, Compound 1-2 and the corresponding compounds were obtained by the synthesis method in Step 159-3 of Example 159, the synthesis method in Step 115-1 of Example 115, and the synthesis method in Example 118, in that order. The structures and spectral data are shown in Table 21 below. [Table 21-1] [Table 21-2]

[0141] Example 352. [7-[4-(1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] Trimethyl orthoformate (0.13 mL, 0.78 mmol) was added to compound 116-1 (50 mg, 0.14 mmol), and the mixture was stirred at 100° C. for 16 hours. The reaction solution was concentrated and then separated using column chromatography to obtain target compound 352 (35 mg, 65%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.78(s,1H),8.27(s,1H),8.22(d,J=8.5Hz,2H),8.17(d,J=8.5Hz,2H),7.93(dd,J=8.8,1.3 Hz,1H),7.55(dd,J=8.9,7.0Hz,1H),7.28(dd,J=7.1,1.4Hz,1H),3.63(t,J=5.4Hz,4H),1.66(d,J=5.2Hz,2H),1.58(s,4H). MS(ESI,LR) Calc. for C 21 H 20 NO2[M+H] + :374.2,found:374.1.

[0142] Example 341 (7-(3-fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 342 (7-(3-nitro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 374 (7-(5-(1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0143] For Examples 341, 342, and 374, Compound 1-2 and the corresponding compounds were obtained by the synthesis methods in Step 159-3 of Example 159, Step 115-1 of Example 115, and Step 352 of Example 352. The structures and spectral data are shown in Table 22 below. [Table 22]

[0144] Example 361. 1-Piperidyl-[7-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone [ka] Compound 116-1 (0.040 g, 0.11 mmol) was dissolved in tetrahydrofuran (2 mL), and trifluoroacetic anhydride (15.3 μL, 23 mg, 0.11 mmol) was added and 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 brine (10 mL × 2). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated. The target compound 361 (45 mg, 92%) was obtained by column chromatography. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.28(s,1H),8.27-8.19(m,4H),7.94(dd,J=8.9,1.3Hz,1H),7.56(dd,J=8. 9,7.1Hz,1H),7.31(dd,J=7.0,1.3Hz,1H),3.63(t,J=5.4Hz,4H),1.66(d,J=5.0Hz,2H),1.62-1.51(m,4H). [MS(ESI,LR) Calc. for C 22 H 19 F3N5O2[M+H] + :442.1,found:442.1.

[0145] Example 359. [7-[4-(5-amino-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] Step 359-1: Compound 116-1 and trichloroacetic anhydride were used to obtain the target compound 359-1 according to the synthesis method in Example 361.

[0146] Step 359-2: Compound 359-1 (130 mg, 0.26 mmol) was added to 7N ammonia solution (1.6 mL, 11.2 mmol) in methanol and stirred at room temperature for 16 hours. The reaction solution was concentrated and then separated by column chromatography to give compound 359 (92 mg, 89%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.26(s,1H),8.09(d,J=8.6Hz,2H),8.04(d,J=8.6Hz,2H),8.01(s,2H),7.91(dd,J=8.9,1.3 Hz,1H),7.54(dd,J=8.9,7.1Hz,1H),7.26(dd,J=7.1,1.4Hz,1H),3.63(t,J=5.4Hz,4H),1.65(d,J=5.1Hz,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 21 H 21 N6O2[M+H] + :389.2,found:389.1.

[0147] Example 348. [7-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] 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 h. After completion of the reaction, the mixture was diluted with dichloromethane (10 mL), washed with aqueous sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give 348-1 (151 mg, 95%).

[0148] Step 348-2: Compound 348-1 (220 g, 0.47 mmol) was placed in a reaction vessel and cooled to 0 °C. Trifluoroacetic acid (1 mL, 13.1 mmol) was added and the mixture was stirred for 1 hour. After the reaction was complete, the mixture was concentrated, diluted with diethyl ether (10 mL) for recrystallization, and then filtered. The residue was dissolved in aqueous sodium bicarbonate and extracted with dichloromethane. The mixture was dried over anhydrous magnesium sulfate, filtered, and concentrated to give 348-2 (140 mg, 65%).

[0149] Step 348-3: N,N-dimethylformamide (2 mL) was placed in a reaction vessel, and 4N hydrochloric acid (0.1 mL, 0.41 mmol) dissolved in 1,4-dioxin was added and stirred for 5 minutes. Imidazole (28.1 mg, 0.41 mmol) was added and stirred for 30 minutes. Compound 348-2 (50 mg, 0.14 mmol) was then added and stirred at 100 °C for 16 hours. Phosphorus oxychloride (15.4 μL, 0.17 mmol) was added and stirred for 12 hours. After the reaction was complete, the temperature was lowered to room temperature, diluted with brine (5 mL), and extracted with dichloromethane (5 mL × 3). The combined organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and recrystallized from N,N-dimethylformamide. The product was then filtered and dried to obtain target compound 348 (14 mg, 26%). 1H NMR(400MHz,DMSO-d6)δ(ppm):8.27(s,1H),8.23-8.10(m,4H),7.93(dd,J=8.9,1.3Hz,1H),7.58-7.51(m,1H),7.29(dd,J=7.0,1.4 Hz, 1H), 3.63 (t, J=5.4Hz, 4H), 2.63 (s, 3H), 1.66 (s, 2H), 1.62-1.53 ​​(m, 4H). MS(ESI, LR) Calc. for C 22 H 22 NO2[M+H] + :388.2,found:388.1.

[0150] Example 364. [7-[6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone 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

[0151] Examples 364 and 379 were obtained by using the corresponding compounds in the same manner as in step 159-3 of Example 159 and the same manner as in Example 348. The structures and spectral data are shown in Table 3 below. [Table 23]

[0152] Example 350. [7-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone Example 380. [7-[5-fluoro-6-(1,3,4-oxadiazol-2-yl)-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0153] Examples 350 and 380 were obtained using compounds 10 and 243, respectively, in the same manner as in steps 348-1 and 348-2 in Example 348 and Example 352. The structures and spectral data are shown in Table 24 below. [Table 24]

[0154] 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 [ka]

[0155] Step 365-1: Using compound 1-2, the target compound 365-1 was obtained by the same synthetic method as in step 1-3 in Example 1.

[0156] Step 365-2: Using compound 365-1, the target compound 365-2 was obtained by the same synthetic method as in Step 243-1 in Example 243.

[0157] Step 365-3: Using compound 365-2, the target compound 365-3 was obtained by the same synthetic method as in Step 348-1 in Example 348.

[0158] Step 365-4: Using compound 365-3, the target compound 365-4 was obtained by the same synthetic method as in Step 348-2 in Example 348.

[0159] Step 365-5: Compound 365-4 (70 mg, 0.15 mmol) was dissolved in 1,4-dioxin (2 mL), followed by the addition of di(imidazol-1-yl)methanedione (39.5 mg, 0.22 mmol) and DBU (88 μL, 0.59 mmol), 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%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):11.81(s,1H),9.20(d,J=2.2Hz,1H),8.62(dd,J=8.2,2.2Hz,1H),8.28(s,1H),8.24(d,J=8.2Hz,1H),7.95(dd,J =8.9,1.3Hz,1H),7.57(dd,J=8.9,7.0Hz,1H),7.41(dd,J=7.1,1.4Hz,1H),3.63(t,J=5.5Hz,4H),1.65(d,J=5.3Hz,2H),1.59(d,J=4.7Hz,4H). MS(ESI,LR) Calc. for C 20 H 19 N6O2S[M+H] + :407.1,found:407.1.

[0160] 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 [ka]

[0161] Step 394-1: Compound 243 was used in the same synthetic method as in Steps 348-1 and 348-2 in Example 348 to obtain the target compound 394-1.

[0162] Step 394-2: Compound 394-1 was used in the same synthesis method as in Example 361 to obtain the target compound 394-2.

[0163] Step 394-3: Compound 394-2 (75 mg, 0.15 mmol) was dissolved in 1,4-dioxin (2 mL), followed by the addition of phosphorus oxychloride (0.15 mL, 1.5 mmol) and stirring at 100 °C for 16 hours. After completion of the reaction, the reaction solution was concentrated, diluted with dichloromethane (5 mL), and adjusted to pH 9 with aqueous sodium bicarbonate. After extraction with dichloromethane (5 mL × 3), the combined organic solution was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography to yield the target compound 394 (7 mg, 9.2%). 1H NMR(400MHz,DMSO-d6)δ(ppm):9.29(t,J=1.5Hz,1H),8.83(dd,J=11.6,1.7Hz,1H),8.33(s,1H),8.02(dd,J=8.8,1.5Hz, 1H),7.60(dd,J=8.8,7.1Hz,1H),7.57-7.52(m,1H),3.64(t,J=5.4Hz,4H),1.66(d,J=6.1Hz,2H),1.58(d,J=4.6Hz,4H). MS(ESI,LR) Calc. for C 21 H 17 F4N6O2[M+H] + :461.1,found:461.1.

[0164] Example 349. 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-3H-1,3,4-oxadiazol-2-one [ka] Compound 348-2 (50 mg, 0.14 mmol) was dissolved in tetrahydrofuran (2 mL), and then 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 target compound 349 (30 mg, 53%). 1 H NMR(400MHz,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=8.9,1.4Hz,1H), 7.54(dd,J=8.9,7.0Hz,1H),7.27(dd,J=7.1,1.3Hz,1H),3.63(t,J=5.4Hz,4H),1.66(q,J=6.2Hz,2H),1.57(q,J=5.7Hz,4H). MS(ESI, LR) Calc. for C 21 H 20 N5O3[M+H] + :390.1,found:390.1.

[0165] Example 360. 5-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]-3H-1,3,4-oxadiazol-2-one 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

[0166] Examples 360 and 373 were obtained using the corresponding compounds by the same synthetic method as in Example 349. The structures and spectral data are shown in Table 25 below. [Table 25]

[0167] Example 300. [7-[4-(2-methylpyrazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone] Example 302. [7-[4-(3-furyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone] Example 305. 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carbonitrile Example 306. [7-[4-(2-hydroxypyrimidin-5-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone Example 307. 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carboxamide Example 324. [7-[4-(3,5-dimethylisoxazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone Example 346. 1-piperidyl-[7-[4-(1H-pyrazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone Example 347. 1-piperidyl-[7-[4-(3-thienyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[0168] Examples 300, 302, 305, 306, 307, 324, 346, and 347 were obtained using compound 292 and the corresponding compounds in the same synthetic method as in steps 1-3 in Example 1. The structures and spectral data are shown in Table 26 below. [Table 26-1] [Table 26-2]

[0169] Example 351. [7-[4-(5-methylthiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka]

[0170] Step 351-1: Compound 292 (0.370 g, 0.96 mmol) was dissolved in N,N-dimethylformamide (10 mL). 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 purged with nitrogen for 10 minutes and then stirred at 90 °C for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with dichloromethane (10 mL), and the 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 purified by column chromatography to give target compound 351-1 (0.528 g, 57%).

[0171] Step 351-2: The target compound 351 was obtained by the same synthetic method as in Step 159-3 in Example 159 using compound 351-1 and 2-bromo-5-methyl-thiazole. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.26(s,1H),8.13-8.01(m,4H),7.91(dd,J=8.8,1.3Hz,1H),7.69(d,J=1.5Hz,1H),7.53 (dd,J=8.9,7.1Hz,1H),7.26(dd,J=7.1,1.4Hz,1H),3.63(t,J=5.4Hz,4H),1.66(d,J=6.8Hz,2H),1.58(d,J=5.0Hz,4H). MS(ESI,LR) Calc. for C 23 H 23 N4OS[M+H] + :403.2,found:403.1.

[0172] Example 358. [7-[4-(1,2-dimethylimidazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] The target compound 358 was obtained by the same synthetic method as in step 351-2 in Example 351 using compound 351-1 and 4-bromo-1,2-dimethyl-imidazole. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.07(s,1H),7.93(d,J=8.8Hz,1H),7.87(s,4H),7.36(dd,J=8.9,7.0Hz,1H),7.17(s, 1H),6.97(d,J=7.1Hz,1H),3.72(t,J=5.3Hz,4H),3.62(s,3H),2.45(s,3H),1.72(q,J=5.6Hz,2H),1.69-1.62(m,4H). MS(ESI,LR) Calc. for C 24 H 26 NO[M+H] + :400.2,found:400.1.

[0173] 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 [ka] Compound 330 was used in the same synthetic method as in Example 7 to obtain target compound 343.

[0174] 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.24(s,1H),7.88(dd,J=8.9,1.3Hz,1H),7.64(t,J=1.5Hz,1H),7.50(dd,J=8.9,7.0Hz,1H),7.39(t,J=1.9Hz, 1H),7.25(t,J=1.9Hz,1H),7.14(dd,J=7.1,1.4Hz,1H),5.64(s,2H),3. 63(t,J=5.4Hz,4H),2.66(s,3H),1.68-1.62(m,2H),1.62-1.55(m,4H). MS(ESI,LR) Calc. for C 22 H 23 N6O2[M+H] + :403.2,found:403.1.

[0175] Example 119 (Z)-5-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzylidene)thiazolidine-2,4-dione [ka]

[0176] Step 119-1: Using compound 1-2 and 3-formylphenylboronic acid, the target compound 119-1 was obtained by the same one synthesis method as in Step 1-3 of Example 1.

[0177] Step 119-2: Compound 119-1 (0.15 g, 0.45 mmol) and thiazolidine-2,4-dinone (0.063 g, 0.54 mmol) were dissolved in ethyl alcohol (5 mL), followed by the addition of piperidine (35 μL, 0.36 mmol) and stirring at 80 °C for 16 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with water (5 mL), and acidified with 1N citric acid (pH 4) to give 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%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.09-8.04(m,2H),8.01-7.83(m,3H),7.67-7.64(m,2 H),7.45(td,J=8.7,4.4Hz,1H),7.06-6.96(m,1H),3.76-3.72(m,4H),1.76-1.69(m, 6H). MS(ESI, LR) Calc. for C 23 H 21 N4O3S[M+H] + :433.1,found:433.1.

[0178] Compound 253. 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzaldehyde oxime [ka] Using compound 119-1, the target compound 253 was obtained by the synthesis method in step 236-2 of Example 236. 1H NMR(400MHz,DMSO-d6)δ(ppm):11.35(s,1H),8.16(t,J=1.8Hz,1H),7.94-7.87(m,2H),7.76(dt,J=7.9,1.4Hz,1H), 7.66-7.48(m,4H),7.20(dd,J=7.1,1.4Hz,1H),3.63(t,J=5.4Hz,4H),1.65(q,J=5.7Hz,2H),1.57(q,J=7.6Hz,4H). MS(ESI,LR) Calc. for C 20 H 21 N4O2[M+H] + :349.2,found:349.1.

[0179] Example 132. 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one [ka] Compound 131 (30 mg, 0.08 mmol) was dissolved in N,N-dimethylformamide (3 mL), and the temperature was lowered to 0 °C. Sodium hydride (60%, 8 mg, 0.2 mmol) was added. The reaction solution was stirred at room temperature for 15 minutes, and then methyl iodide (7.5 μL, 0.12 mmol) was added and stirred for 1 hour. After the reaction was completed, the temperature was lowered to 0 °C, and the reaction solution was diluted with water (10 mL) and extracted with dichloromethyl methyl (10 mL × 3). The combined organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated using column chromatography to obtain the target compound 132 (13.8 mg, 44%). 1H NMR(400 MHz,DMSO-d6)δ(ppm):8.41(d,J=2.0Hz,1H),8.24(s,1H),8.00(dd,J=7.9,2.0Hz,1H),7.89(dd,J=8.9,1.4Hz,1H),7.55-7 .45(m,2H),7.19(dd,J=7.0,1.4Hz,1H),3.63(t,J=5.5Hz,6H),3.08(d,J=7.4Hz,5H),1.69-1.62(m,2H),1.62-1.55(m,4H). MS(ESI,LR) Calc. for C 23 H 25 N4O2[M+H] + :389.2,found:389.2.

[0180] Example 199. 6-methyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5-(6H)-one [ka] Compound 195 and the corresponding compound were used to obtain target compound 199 according to the synthesis method in Example 132. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.09(d,J=2.3Hz,1H),8.78(d,J=2.3Hz,1H),8.27(s,1H),7.93(dd,J=8.9,1.4Hz,1H),7.54(dd,J=8.9,7.1Hz,1H),7.3 3(dd,J=7.1,1.3Hz,1H),3.73(t,J=6.8Hz,2H),3.63(t,J=5.4Hz,4H),3.24 (t,J=6.8Hz,2H),3.09(s,3H),1.66(d,J=6.1Hz,2H),1.57(d,J=7.3Hz,4H). MS(ESI, LR) Calc. for C 22 H24 NO2[M+H] + :390.2,found:390.1.

[0181] Example 133. 2-Isopropyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one [ka] The target compound 133 was obtained by the synthesis method in Example 132 using compound 131 and isopropyl iodide. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.41(d,J=2.0Hz,1H),8.24(s,1H),7.98(dd,J =7.9,2.0Hz,1H),7.88(dd,J=8.9,1.3Hz,1H),7.54-7.46(m,2H),7.19(dd,J= 7.0,1.4Hz,1H),4.89(p,J=6.8Hz,1H),3.63(t,J=5.4Hz,4H),3.50(t,J=6.5H z,2H),3.03(t,J=6.5Hz,2H),1.65(s,2H),1.57(s,4H),1.17(d,J=6.8Hz,6H). MS(ESI,LR) Calc. for C 25 H 29 N4O2[M+H] + :417.2,found:417.1.

[0182] Example 135. 2-methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one [ka] Compound 134 and methyl iodide were used to obtain target compound 135 according to the synthesis method in Example 132. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.80(d,J=1.9Hz,1H),8.27(s,1H),8.23(dd,J=8.3 ,2.0Hz,1H),7.91(dd,J=8.9,1.3Hz,1H),7.82(d,J=8.4Hz,1H),7.60(d,J=7.3Hz, 1H),7.54(dd,J=8.9,7.0Hz,1H),7.28(dd,J=7.1,1.4Hz,1H),6.72(d,J=7.3Hz,1H ),3.63(t,J=5.4Hz,4H),3.55(s,3H),1.65(d,J=7.8Hz,2H),1.57(d,J=7.7Hz,4H). MS(ESI,LR) Calc. for C 23 H 23 N4O2[M+H] + :387.2,found:387.1.

[0183] Example 137. 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one [ka] Compound 136 and methyl iodide were used to obtain target compound 137 according to the synthesis method in Example 132. 1H NMR(400MHz,DMSO-d6)δ(ppm):8.26(s,1H),8.04-7.99(m,1H),7.93-7.86(m,3H),7.52(dd,J=8.9,7.0Hz,1H) ,7.22(dd,J=7.1,1.4Hz,1H),3.62(t,J=5.5Hz,6H),3.08(s,5H),1.65(q,J=5.8Hz,2H),1.57(d,J=6.8Hz,4H). MS(ESI,LR) Calc. for C 23 H 25 N4O2[M+H] + :389.2,found:389.1.

[0184] Example 139. 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one [ka] The target compound 139 was obtained by the synthesis method in Example 132 using compound 138 and methyl iodide. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.35(d,J=8.4Hz,1H),8.28(s,1H),8.23(d,J=1.7Hz,1H),8.01(dd,J=8.4,1.8Hz,1H),7.94(dd,J=8.9,1.3Hz,1H ),7.56(dd,J=8.9,7.1Hz,2H),7.30(dd,J=7.0,1.4Hz,1H),6.72(d,J=7.3Hz,1H),3.63(t,J=5.5Hz,4H),3.56(s,3H),1.66(s,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 23 H 23 N4O2[M+H] + :387.2,found:387.1.

[0185] Example 141. 2-methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one [ka] Compound 140 and methyl iodide were used to obtain target compound 141 according to the synthesis method in Example 132. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.28-8.22(m,2H),8.12(dd,J=7.9,1.7Hz,1H),7.91(dd,J=8.9,1.3Hz,1H),7.77(d,J=7.9Hz,1H),7.53( dd,J=8.9,7.0Hz,1H),7.26(dd,J=7.1,1.4Hz,1H),4.58(s,2H),3.63(t,J=5.4Hz,4H),3.13(s,3H),1.65(d,J=8.0Hz,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 22 H 23 N4O2[M+H] + :375.2,found:375.1.

[0186] Example 142. 2-Isopropyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one [ka] Compound 140 and isopropyl iodide were used to obtain target compound 142 according to the synthesis method in Example 132. 1H NMR(400MHz,DMSO-d6)δ(ppm):8.29-8.21(m,2H),8.11(dd,J=7.9,1.7Hz,1H) ,7.91(dd,J=8.9,1.4Hz,1H),7.78(d,J=7.9Hz,1H),7.53(dd,J=8.9,7.0Hz,1 H),7.25(dd,J=7.1,1.4Hz,1H),4.56(s,2H),4.47(p,J=6.7Hz,1H),3.63(t,J =5.4Hz,4H),1.72-1.63(m,2H),1.57(d,J=7.3Hz,4H),1.28(d,J=6.8Hz,6H). MS(ESI,LR) Calc. for C 24 H 27 N4O2[M+H] + :403.2,found:403.1.

[0187] Example 144. 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one [ka] Compound 143 and methyl iodide were used to obtain target compound 144 according to the synthesis method in Example 132. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.26(s,1H),8.15(s,1H),8.01(dd,J=7.9,1.6Hz,1H),7.92(dd,J=9.0,1.3Hz,1H),7.83(d,J=7.9Hz,1H),7. 54(dd,J=8.9,7.0Hz,1H),7.24(dd,J=7.1,1.4Hz,1H),4.57(s,2H),3.63(t,J=5.4Hz,4H),3.13(s,3H),1.66(d,J=5.4Hz,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 22 H 23N4O2[M+H] + :375.2,found:375.1.

[0188] Example 259. [7-(3-amino-1,2-benzoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] Potassium tert-butylate (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 the mixture was filtered. The filtrate was separated using column chromatography to obtain the target compound 259 (36 mg, 33%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.41(d,J=1.9Hz,1H),8.26(s,1H),8.06(dd,J=8.8,1.8Hz,1H),7.90(dd,J=8.9,1.4Hz,1H),7.62(d,J=8.8Hz ,1H),7.54(dd,J=8.9,7.0Hz,1H),7.18(dd,J=7.1,1.4Hz,1H),6.55(s,2H),3.63(t,J=5.5Hz,4H),1.66(d,J=5.6Hz,2H),1.62-1.50(m,4H). MS(ESI,LR) Calc. for C 20 H 20 NO2[M+H] + :362.2,found:362.1

[0189] Example 320. [7-(3-amino-1,2-benzoxazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] Compound 22 was used to obtain target compound 320 by the synthesis method in Example 259. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.26(s,1H),8.04(s,1H),7.98(d,J=8.2Hz,1H),7.92(dd,J=8.9,1.4Hz,1H),7.77(dd,J=8.2,1.4Hz, 1H),7.54(dd,J=8.9,7.0Hz,1H),7.27(dd,J=7.0,1.4Hz,1H),6.54(s,2H),3.63(t,J=5.4Hz,4H),1.66(s,2H),1.57(d,J=7.4Hz,4H). MS(ESI,LR) Calc. for C 20 H 20 NO2[M+H] + :362.2,found:362.1.

[0190] Example 260. [7-(3-amino-1H-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] Compound 254 (100 mg, 0.29 mmol) was dissolved in ethyl alcohol (3 mL), and then hydrazine hydrate (35.9 mg, 0.57 mmol) was added. 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 residue was separated using column chromatography to obtain target compound 260 (85 mg, 33%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):11.64(s,1H),8.32-8.21(m,2H),7.81(ddd,J=20.3,8.8,1.5Hz,2H),7.51(dd,J=8.9,7.0Hz, 1H),7.40-7.32(m,1H),7.12(dd,J=7.1,1.4Hz,1H),5.51(s,2H),3.63(t,J=5.4Hz,4H),1.65(d,J=5.3Hz,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 20 H 21 NO[M+H] + :361.2,found:361.1.

[0191] Example 309. 7-(3-amino-1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone [ka] Compound 22 was used to obtain target compound 309 by the synthesis method in Example 260. 1H NMR(400MHz,DMSO-d6)δ(ppm):11.62(s,1H),8.24(d,J=1.1Hz,1H),7.90-7.85(m,2H),7.83(d,J=8.4Hz,1H),7.52(dd,J=8.8,7.1Hz, 1H),7.40-7.34(m,1H),7.22(dd,J=7.1,1.4Hz,1H),5.45(s,2H),3.63(t,J=5.3Hz,4H),1.66(d,J=6.9Hz,2H),1.58(d,J=7.3Hz,4H). MS(ESI,LR) Calc. for C 20 H 21 NO[M+H] + :361.2,found:361.1.

[0192] Example 261. [7-(3-amino-1-methyl-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone Example 310. [7-(3-amino-1-methyl-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0193] Examples 261 and 310 were obtained from compounds 254 and 22, respectively, using methylhydrazine by the synthesis method in Example 260. The structures and spectral data are shown in Table 27 below. [Table 27]

[0194] 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 [ka]

[0195] Step 395-1: Compound 1-2 and 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]acetonitrile were used to obtain the target compound 395-1 using the synthetic method in Step 159-3 of Example 159.

[0196] Step 395-2: Using compound 395-1 and DIPEA, the target compound 395-2 was obtained according to the synthesis method in Step 115-1 of Example 115.

[0197] Step 395-3: Compound 395-2 (100 mg, 0.27 mmol) was added with trimethyl orthoformate (1.49 mL, 13.6 mmol) and trifluoroacetic acid (8.3 μL) and stirred at 60 °C for 1 h. After completion of the reaction, the reaction solution was diluted with dichloromethane (10 mL) and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then purified by column chromatography to give the target compound 395 (39 mg, 38%). 1H NMR(400MHz,DMSO-d6)δ(ppm):9.64(s,1H),9.13(s,1H),8.48(s,1H),8.35(s,1H),7.78(dd,J=8.7,1.4Hz,1H),7.58(dd,J=7 .3,1.4Hz,1H),7.50(dd,J=8.7,7.2Hz,1H),5.80(s,2H),3.62(t,J=5.4Hz,4H),1.65(d,J=5.5Hz,2H),1.57(d,J=5.6Hz,4H). MS(ESI,LR) Calc. for C 19 H 20 N7O2[M+H] + :378.2,found:378.1.

[0198] 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 [ka] Compound 395-5 was used to obtain target compound 396 by the synthesis method in Example 349. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.95(s,1H),8.43(s,1H),8.36(s,1H),7.77(d,J=8.8Hz,1H),7.56 (t,J=6.3Hz,1H),7.51-7.47(m,1H),5.10(s,2H),3.63(t,J=5.5Hz,4H),1.66(s,2H),1.57(s,4H). MS(ESI,LR) Calc. for C 19 H 20 N7O3[M+H] + :394.2,found:394.1.

[0199] 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 [ka]

[0200] Step 397-1: Compound 1-2 was used to obtain the target compound 397-1 by the synthesis method in Step 159-3 of Example 159.

[0201] Step 397-2: Compound 397-1 was used to obtain target compound 397-2 by the synthesis method in Step 395-1 of Example 395.

[0202] Step 397-3: Compound 397-2 was used to obtain the target compound 397-3 by the synthesis method in Step 395-2 of Example 395.

[0203] Step 397-4: Compound 397 was obtained by the synthesis method in Step 395-3 of Example 395 using compound 397-3. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.64(s,1H),8.71(d,J=5.2Hz,1H),8.56(s,1H) ,8.29(s,1H),8.21(s,1H),8.15(s,1H),7.97(dd,J=8.9,1.4Hz,1H),7.78(dd, J=5.2,1.6Hz,1H),7.56(dd,J=8.9,7.0Hz,1H),7.39(dd,J=7.0,1.4Hz,1H),5. 69(s,2H),3.63(t,J=5.4Hz,4H),1.66(d,J=5.6Hz,2H),1.57(d,J=6.7Hz,4H). MS(ESI,LR) Calc. for C 24 H 23 N8O2[M+H] + :455.2,found:455.1.

[0204] Example 146. 4-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)benzonitrile [ka] 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-dioxin (2 mL), filled with nitrogen, and stirred at 100 °C for 16 h. After completion of the reaction, the reaction solution was diluted with dichloromethane (10 mL) and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and then separated using column chromatography to obtain the target compound 146 (16 mg, 32%) [BINAP(2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)]. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.72(s,1H),8.28(s,1H),7.85-7.73(m,2H),7.58-7.50(m,2H),7.49-7.3 5(m,2H),6.88(dd,J=7.1,1.5Hz,1H),3.61(t,J=5.4Hz,4H),1.65(d,J=5.4Hz,2H),1.57(d,J=7.3Hz,4H). MS(ESI,LR) Calc. for C 20 H 20 NO[M+H] + :346.2,found: 346.1.

[0205] Example 147. 3-((3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)pyridin-2(1H)-one Example 148. Piperidin-1-yl(7-((pyrimidin-2-ylmethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone Example 149. Piperidin-1-yl(7-((2-(pyridin-4-yl)ethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone Example 150 (7-((1-methylpiperidin-4-yl)amino)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 211. 7-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-3,4-dihydro-2H-isoquinolin-1-one Example 212. 6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]isoindolin-1-one Example 238. [7-[(4-chlorophenyl)methylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone Example 242. [7-[2-(4-chlorophenyl)ethylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0206] Examples 147, 148, 149, 150, 211, 212, 238, and 242 were obtained using Compound 1-2 and the corresponding compounds by the synthesis method in Example 146. The structures and spectral data are shown in Table 28 below. [Table 28-1] [Table 28-2]

[0207] Example 194 (7-((3-methoxyphenyl)thio)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] 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-methoxybenzinethiol (71.05 mg, 0.51 mmol) were dissolved in 1,4-dioxin (2 mL) and the mixture was purged with nitrogen and stirred at 100 °C for 1 h. After completion of the reaction, the reaction solution was diluted with dichloromethane (10 mL) and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and purified by column chromatography to give compound 194 (61 mg, 98%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.32(s,1H),7.68(dd,J=8.8,1.2Hz,1H),7.50(t,J=8.2Hz,1H),7.32(dd,J=8.8,7.4Hz,1H),7.29-7. 22(m,2H),7.20-7.14(m,1H),6.34(dd,J=7.3,1.2Hz,1H),3.81(s,3H),3.60(t,J=5.4Hz,4H),1.72-1.60(m,2H),1.60-1.48(m,4H). MS(ESI,LR) Calc. for C 20 H 22 N3O2S[M+H] + :368.1,found:368.1.

[0208] Example 235. 4-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-1H-pyrimidin-6-one [ka] The target compound 235 was obtained by the synthesis method in Example 194 using compound 1-2, palladium acetate, and the corresponding compound. 1 H NMR(400MHz,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=5.4Hz,4H),1.71-1.61(m,2H),1.56(d,J=7.9Hz,4H). MS(ESI,LR) Calc. for C 17 H 19 N6O2[M+H] + :339.1,found:339.1.

[0209] Example 236. 3-methyl-6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]pyrimidin-4-one [ka]

[0210] Step 236-1: Compound 236-1 was obtained by the synthesis method in Example 146 using compound 1-2 and diphenylmethanimine.

[0211] Step 236-2: Compound 236-1 (2 g, 4.89 mmol), hydroxylamine 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 purified by column chromatography to give compound 236-2 (845 mg, 69%).

[0212] Step 236-3: Compound 236 was obtained by the synthesis method in Example 235 using compound 236-2 and 6-bromo-3-methyl-pyrimidin-4-one. 1H NMR(400MHz,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=5.4Hz,4H),3.38(s,3H),1.65(q,J=5.7Hz,2H),1.57(q,J=5.8Hz,4H). MS(ESI,LR) Calc. for C 18 H 21 N6O2[M+H] + :353.2,found:353.1.

[0213] Example 239. 4-chloro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzamide [ka] Compound 236-2 (70 mg, 0.28 mmol) was dissolved in pyridine (2.6 mL), and then dimethylaminopyridine (17.5 mg, 0.14 mmol) and 4-chlorobenzoyl chloride (75.2 mg) were added and stirred at room temperature for 16 hours. The reaction solution was concentrated, and the residue was separated by column chromatography to obtain target compound 239 (60 mg, 53%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.25(d,J=8.2Hz,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). MS(ESI,LR) Calc. for C 20 H 20 ClN4O2[M+H] + :383.1,found:383.1.

[0214] Example 240. 1,3,5-trimethyl-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrazole-4-sulfonamide Example 241. 5-fluoro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide

[0215] For Examples 240 and 241, Compound 236-2 and the corresponding compounds were used to obtain them by the synthesis method in Example 239. The structures and spectral data are shown in Table 29 below. [Table 29]

[0216] Example 151. 1-(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)pentan-1-one [ka]

[0217] Step 151-1: Using pyrazolo[1,5-a]pyridine-3-carboxylic acid, the target compound 151-1 was obtained using a synthetic method similar to Step 1-2 in Example 1.

[0218] Step 151-2: Compound 151-1 (1 g, 4.36 mmol) was dissolved in tetrahydrofuran (15 mL). The temperature was then lowered to -78 °C, and N-butyl ammonium hydroxide (2.5 M solution, 2.44 mL, 6.1 mmol) was added. The reaction mixture was stirred for 30 minutes, and then 1,2-iodoethane (1.47 g, 5.23 mmol) dissolved in tetrahydrofuran (9 mL) was added. The reaction mixture was stirred for 3 hours, then warmed to room temperature and diluted with saturated aqueous sodium bicarbonate (20 mL) and dichloromethane (20 mL). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography to give the target compound 151-2 (151 mg, 11%).

[0219] Step 151-3: Compound 151-2 was synthesized in the same manner as in Step 1-3 of Example 1 to obtain target compound 151. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.35(d,J=2.2Hz,1H),8.78(d,J=2.2Hz,1H),8.54(d d,J=8.8,1.4Hz,1H),8.41(s,1H),8.20(d,J=8.5Hz,1H),7.95(d,J=8.1Hz,1H),7.82 (ddd,J=8.4,6.9,1.5Hz,1H),7.70-7.56(m,2H),7.23(dd,J=7.1,1.4Hz,1H),2.93( t,J=7.5Hz,2H),1.79(p,J=7.6Hz,2H),1.46(h,J=7.4Hz,2H),0.98(t,J=7.3Hz,3H). MS(ESI,LR) Calc. for C 21 H 20 NO[M+H] + :330.2,found:330.2.

[0220] Example 152. 4-(3-acetylpyrazolo[1,5-a]pyridin-7-yl)benzonitrile [ka]

[0221] Step 152-1: The target compound 152-1 was obtained by the same synthetic method as in Step 1-3 of Example 1 using pyrazolo[1,5-a]pyridine-3-carboxylic acid and 4-cyanophenylboronic acid.

[0222] Step 152-2: Using compound 152-1 and dimethylhydroxylamine, the target compound 152-2 was obtained by the same synthetic method as in Step 1-2 in Example 1.

[0223] Step 152-3: Compound 152-2 (0.05 mg, 0.16 mmol) was dissolved in tetrahydrofuran (2 mL). The temperature was then lowered to 0 °C, and methylmagnesium bromide (3 M solution, 0.1 mL, 0.33 mmol) was slowly added. The reaction solution was stirred for 3 hours and diluted with saturated aqueous ammonium chloride (10 mL) and ethyl acetate (10 mL). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography to give the target compound 152 (11 mg, 24%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.72(s,1H),8.36(dd,J=8.8,1.3Hz,1H),8.14(d,J=8.3Hz,2H) ,8.05(d,J=8.4Hz,2H),7.76(dd,J=8.8,7.2Hz,1H),7.43(dd,J=7.2,1.4Hz,1H),2.54(s,3H). MS(ESI,LR) Calc. for C 16 H 12 NO[M+H] + :262.1,found:262.1.

[0224] Example 153. 4-(3-(2-hydroxypropan-2-yl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile [ka] The target compound 153 was obtained using compound 152-2 in the same synthetic method as in step 152-3 in Example 152. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.72(s,1H),8.35(dd,J=8.8,1.3Hz,1H),8.17-8.11(m,2H),8.08(d ,J=8.5Hz,2H),7.76(dd,J=8.8,7.1Hz,1H),7.41(dd,J=7.2,1.4Hz,1H),2.67(s,3H),2.55(s,3H). MS(ESI,LR) Calc. for C 17 H 15 N2O2[M+H] + :279.1,found:279.1.

[0225] Example 154. 7-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one [ka]

[0226] Step 154-1: Using compound 1-1 and 4-fluoropiperidine, the target compound 154-1 was obtained in the same synthetic manner as in Step 1-2 of Example 1.

[0227] Step 154-2: The target compound 154 was obtained by 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. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.41(d,J=2.0Hz,1H),8.30(s,1H),8.07(s,1H),8.01(dd,J=7.9,2.0Hz,1H),7.92(dd,J=8.9,1.3Hz,1H),7.57-7.4 8(m,2H),7.21(dd,J=7.1,1.4Hz,1H),3.80-3.62(m,4H),3.45(td,J=6.6 ,2.7Hz,2H),3.02(t,J=6.5Hz,2H),2.06-1.82(m,3H),1.82-1.67(m,2H). MS(ESI,LR) Calc. for C 22 H 22 FN4O2[M+H] + :393.2,found:393.1.

[0228] Example 155. 6-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 156. 4-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile Example 157 (4-fluoropiperidin-1-yl)(7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)methanone Example 231. 6-(3-(4-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methylisoindolin-1-one

[0229] Examples 155, 156, 157, and 231 were obtained using compound 154-1 and the corresponding compounds by the same synthetic method as in steps 1-3 in Example 1. The structures and spectral data are shown in Table 30 below. [Table 30]

[0230] Example 158. Cyclohexyl(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone [ka]

[0231] Step 158-1: Using pyrazolo[1,5-a]pyridine-3-carboxylic acid and phenylboronic acid, the target compound 158-1 was obtained by the same synthetic method as in Step 1-3 of Example 1.

[0232] Step 158-2: Using compound 158-1 and dimethylhydroxylamine, the target compound 158-2 was obtained by the same synthetic method as in Step 1-2 in Example 1.

[0233] Step 158-3: Using compound 158-2 and cyclohexylmagnesium bromide, the target compound 158 was obtained in the same synthetic manner as in Step 152-3 in Example 152. 1H NMR(400MHz,DMSO-d6)δ(ppm):8.75(s,1H),8.33(dd,J=8.8,1.4Hz,1H),7.97-7.86(m,2H),7.72(dd,J=8.8,7.2Hz,1H),7.57( dd,J=5.2,2.0Hz,3H),7.31(dd,J=7.1,1.4Hz,1H),3.23(s,1H),1.91-1.64(m,5H),1.53-1.35(m,4H),1.22(d,J=11.4Hz,1H). MS(ESI,LR) Calc. for C 20 H 21 NO[M+H] + :305.2,found:305.1.

[0234] Example 227: (2-azabicyclo[2.2.1]heptan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone Example 228. (2-azabicyclo[2.2.2]octan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone Example 229. (7-azabicyclo[2.2.1]heptan-7-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[0235] Examples 227, 228, and 229 were obtained using compound 158-1 and the corresponding compounds by the same synthetic method as in steps 1 and 2 in Example 1. The structures and spectral data are shown in Table 31 below. [Table 31]

[0236] Example 234. 6-(3-(4,4-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 378. 6-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 382. 6-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 385. (R)-6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 386 (S)-6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 387. 6-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 390. 6-(3-(2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 391. 6-(3-(6-azaspiro[3.4]octane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 392. 6-(3-(7-azaspiro[3.5]nonane-7-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 393. 6-(3-(3-ethylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 398. 6-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 400. 6-(3-(3-isopropylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 401. 6-(3-(1,2,3,6-tetrahydropyridine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 405. 6-(3-(6-azaspiro[3.5]nonane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 411. 6-(3-(6-fluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one Example 412. 6-(3-(6,6-difluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[0237] For Examples 234, 378, 382, ​​385, 386, 387, 390, 391, 392, 393, 398, 400, 401, 405, 411, and 412, intermediates were obtained using compound 1-1 and the corresponding compound in the same synthetic method as in step 1-2 of Example 1, and then 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one in the same synthetic method as in step 1-3 of Example 1. The structures and spectral data are shown in Table 32 below. [Table 32-1] [Table 32-2] [Table 32-3]

[0238] Example 336 (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methylpiperidin-1-yl)methanone Example 337 (3-ethylpiperidin-1-yl)(7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone Example 338 (7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-(trifluoromethyl)piperidin-1-yl)methanone

[0239] In Examples 336, 337, and 338, intermediates were obtained using compound 1-1 and the corresponding compound in the same synthetic method as in step 1-2 of Example 1, and then (6-fluoro-3-pyridyl)boronic acid was used to obtain the intermediates in the same synthetic method as in step 1-3 of Example 1. The structures and spectral data are shown in Table 33 below. [Table 33]

[0240] Example 339. 3-(5-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one Example 353. 3-(5-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one Example 354. 3-(5-(3-(3-ethylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one Example 383. 3-(5-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one Example 384. 3-(5-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[0241] In regard to Examples 339, 353, 354, 383, and 384, intermediates were obtained using compound 1-1 and the corresponding compound in the same synthetic method as in step 1-2 in Example 1, and then the compounds were obtained in the same synthetic method as in Example 316. The structures and spectral data are shown in Table 34 below. [Table 34]

[0242] Example 340. N-(2-nitrobenzyl)-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide [ka] Compound 101 and the corresponding compound were used to obtain target compound 340 by the synthesis method in Example 132. 1H NMR(400MHz,DMSO-d6)δ(ppm):8.61(d,J=2.2Hz,1H),8.52(dd,J=4.9,1.7Hz,1H),8. 18(s,1H),8.06(dd,J=8.1,1.3Hz,1H),7.89-7.81(m,5H),7.78(td,J=7.6,1.3Hz,1H ),7.61-7.53(m,1H),7.45(dd,J=8.7,6.6Hz,3H),7.35(dd,J=7.9,4.9Hz,1H),7.10( dd,J=7.1,1.4Hz,1H),5.50(s,2H),3.59(t,J=5.4Hz,4H),1.63(m,2H),1.55(m,4H). MS(ESI,LR) Calc. for C 32 H 29 N6O4[M+H] + :561.2,found:561.1.

[0243] Example 356 (7-(2-(4-amino-1H-pyrazol-1-yl)-6-bromopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka]

[0244] Step 356-1: Compound 1-2 and 2-bromo-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine were used in the same synthetic method as in Step 159-3 of Example 159 to obtain the target compound 356-1.

[0245] Step 356-2: Compound 356-1 was used in accordance with the synthesis method in Example 344 to obtain the target compound 356. 1H NMR(400MHz,DMSO-d6)δ(ppm):8.42(d,J=1.3Hz,1H),8.32(s,1H),8.02-7.97(m,2H),7.82(d,J=0.9Hz,1H),7.55(dd,J=8.8,7.1Hz, 1H),7.48(dd,J=7.1,1.5Hz,1H),7.46-7.42(m,1H),4.44(s,2H),3.63(t,J=5.4Hz,4H),1.66(d,J=5.7Hz,2H),1.58(d,J=7.0Hz,4H). MS(ESI,LR) Calc. for C 21 H 21 BrNO[M+H] + :466.1,found:466.0.

[0246] Example 363 (7-(5-bromo-2-(3-(hydroxymethyl)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] Using compound 356-1, the target compound 363 was obtained by the same synthetic method as in Example 221. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.31(d,J=2.4Hz,1H),8.24(s,1H),7.92(dd,J=9.0,1.4Hz,1H),7.80(d,J=2.4Hz,1H),7.49(dd,J=8.9,6.9H z,1H),7.11(dd,J=7.0,1.4Hz,1H),4.56(t,J=5.2Hz,1H),3.62(t,J=5.5Hz,4H),3.18(m,2H),2.48-2.36(m,1H),1.66(m,2H),1.57(m,4H). MS(ESI,LR) Calc. for C 22 H25 BrNO2[M+H] + :470.1,found:470.1.

[0247] Example 345. (7-(3-(3-hydroxyazetidin-1-yl)-5-(isoxazol-4-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 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 Example 366 (7-(2-(isoxazol-4-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 369 (7-(2-(1-methyl-1H-pyrazol-5-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 371 (7-(2-(3,5-dimethylisoxazol-4-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 376 (7-(5'-fluoro-6-morpholino-[2,3'-bipyridin]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 377 (7-(2-(2-methylpyrimidin-5-yl)-6-morpholinopyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 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 Example 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 Example 370. 3-(5'-fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[2,3'-bipyridin]-6-yl)oxazolidin-2-one Example 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 Example 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

[0248] For Examples 345, 357, 366, 369, 371, 376, 377, 367, 368, 370, 372, and 375, intermediates were obtained using compound 356-1 and the corresponding compound in the same synthetic method as in step 356-2 of Example 356-1, and then the intermediates were obtained using the same synthetic method as in Example 344. The structures and spectral data are shown in Table 35 below. [Table 35-1] [Table 35-2] [Table 35-3]

[0249] Example 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 [ka] Example 325 was obtained using compound 265 and (2-methylpyrazol-3-yl)boronic acid in the same synthetic method as in step 159-3 in Example 159. 1H NMR(400MHz,DMSO-d6)δ(ppm):8.64(d,J=2.4Hz,1H),8.54(dd,J=8.7,2.5Hz,1H),8.24(s,1H),8.00(dd,J=8.9,1.3Hz,1H),7 .63-7.49(m,2H),7.36(d,J=7.0Hz,1H),6.64(d,J=1.9Hz,1H),3.95(s,3H),3.63(t,J=5.4Hz,4H),1.66(m,2H),1.58(m,4H). MS(ESI,LR) Calc. for C 21 H 23 FN6O[M+H] + :405.2,found:405.1.

[0250] Example 381. [7-[6-(3,5-dimethylisoxazol-4-yl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone Example 399. [7-[2-(3,5-dimethylisoxazol-4-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone

[0251] Examples 381 and 399 were obtained from compounds 281 and 267, respectively, using (3,5-dimethylisoxazol-4-yl)boronic acid in the same synthetic manner as in step 159-3 in Example 159. The structures and spectral data are shown in Table 36 below. [Table 36]

[0252] Example 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] [ka] The target compound 404 was obtained using compound 404-1, [5-(difluoromethyl)-1,3,4-thiadiazol-2-yl]boronic acid, and potassium carbonate in the same synthetic method as in step 159-3 in Example 159. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.56(s,2H),8.31(s,1H),7.99(d,J=8.8Hz,1H),7.61-7.57(m,1H),7.50(d ,J=6.4Hz,1H),7.33(t,J=52.8Hz,1H),3.63(t,J=5.0Hz,4H),1.66(d,J=4.4Hz,2H),1.57(d,J=3.6Hz,4H). MS(ESI,LR) Calc. for C 20 H 18 F2N7O2S[M+H] + :458.1,found:458.1.

[0253] Example 159. 7-(2-amino-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one [ka]

[0254] Step 159-1: Compound 159-1 (synthesized with reference to the literature "Belarousai, R. et al. Synthesis 2013, 45, 2557-2566. Convenient Synthesis of New N-3-Substituted Pyrido[1',2':1,5]pyrazolo[3,4-d]pyrimidine-2,4(1H,3H)dione Derivatives") was used to obtain target compound 159-2 by a synthetic method similar to that of Step 1-2 in Example 1.

[0255] Step 159-2: Using compound 159-2, the target compound 159-3 was obtained by the same synthetic method as in Step 1-1 in Example 1.

[0256] Step 159-3: Compound 159-3 (0.118 g, 0.25 mmol) was dissolved in 1,4-dioxin (5 mL). 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-isoquinolin-1-one (0.082 g, 0.3 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.021 g, 0.03 mmol), and 2 M aqueous cesium carbonate solution (0.38 mL, 0.75 mmol) were added. The reaction mixture was then flushed with nitrogen and stirred at 100 °C for 12 hours. After completion of the reaction, the mixture was cooled to room temperature, diluted with dichloromethane (10 mL), and the palladium was removed using diatomaceous earth (Celite). The organic layer was washed with water and brine, then dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated by column chromatography to give the target compound 159-4 (117 mg, 95%).

[0257] Step 159-4: Compound 159-4 (50 mg, 0.1 mmol) was added to a 4N solution of 1,4-dioxin in hydrochloric acid (2.56 mL) and stirred for 2 hours. After completion of the reaction, the reaction solution was concentrated and separated using column chromatography to obtain the target compound 159 (25.1 mg, 63%). 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.25(d,J=2.0Hz,1H),8.05(d,J=3.0Hz,1H),7.92(dd,J=7.8,2.0Hz,1H),7.46(d,J=7.9Hz,1H),7.40-7.29( m,2H),6.84(dd,J=6.2,2.3Hz,1H),5.62(s,2H),3.45(dq,J=13.3,4.1Hz,6H),3.00(t,J=6.5Hz,2H),1.62-1.63(m,2H),1.56-1.54(m,4H). MS(ESI,LR) Calc. for C 22 H 24 NO2[M+H] + :390.2,found:390.2.

[0258] Example 160. 7-(2-amino-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one [ka]

[0259] Step 160-1: Compound 159-4 (0.078 g, 0.16 mmol) was dissolved in N,N-dimethylformamide (3 mL), and methyl iodide (11.8 μL, 0.19 mmol) and cesium carbonate (0.062 g, 0.19 mmol) were added and stirred for 12 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth (Celite) and washed with ethyl acetate. The filtrate was concentrated and then separated using column chromatography to obtain the target compound 160-1 (75 mg, 94%).

[0260] Step 160-2: Compound 160-1 was subjected to a synthetic method similar to that of Step 159-4 in Example 159 to obtain target compound 160. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.44(d,J=2.0Hz,1H),8.08(dd,J=7.9,2.0Hz,1H), 8.01(d,J=3.0Hz,1H),7.47(d,J=8.0Hz,1H),7.37(dd,J=8.8,7.0Hz,1H),7.30(dd, J=8.8,1.5Hz,1H),6.89(dd,J=7.0,1.5Hz,1H),5.75(q,J=4.8Hz,1H),3.45(tt,J=6 .6,3.0Hz,5H),3.00(t,J=6.6Hz,2H),2.79(d,J=5.0Hz,3H),1.62(d,J=7.0Hz,2H). MS(ESI,LR) Calc. for C 23 H 26 NO2[M+H] + :404.2,found:404.1.

[0261] Example 161 (7-(3-chlorophenyl)-1H-indazol-3-yl)(piperidin-1-yl)methanone [ka] The target compound 161 was obtained by the same synthetic method as in Example 154 using 7-bromo-1H-indazole-3-carboxylic acid and the corresponding compound. 1 H NMR(400MHz,DMSO-d6)δ(ppm):7.96(d,J=8.0Hz,1H),7.75(s,1H),7.71-7.65(m,1H),7.58(t,J=7.7H z,1H),7.55-7.45(m,2H),7.32(dd,J=8.2,7.1Hz,1H),3.79(d,J=63.1Hz,4H),1.63(d,J=37.2Hz,6H). MS(ESI,LR) Calc. for C 19 H 19 ClNO[M+H] + :340.1,found:340.1.

[0262] Example 162 (8-(3-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka]

[0263] Step 162-1: Methyl tert-butyl ether (TBME) (200 mL) was placed in a reaction vessel and, under nitrogen pressure, sodium ethyl acetate (20% solution, 27.7 mL, 71.8 mmol) was added. After stirring for 15 minutes, the temperature was lowered to 0°C. Ethyl chloroacetate (6.99 mL, 65.28 mmol) and ethyl formate (6.82 mL, 84.8 mmol) were added over 1 hour. After stirring for 30 minutes, the temperature was raised to room temperature and stirred for 18 hours. The temperature was then lowered to 5-10°C, and water (100 mL) was added and stirred for 30 minutes or more. The reaction solution was acidified with hydrochloric acid (pH 1-2), the temperature was raised to room temperature, and the mixture was stirred for 30 minutes. The organic layer was separated, and the aqueous layer was extracted with methyl tert-butyl ether. The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to give the target compound 162-1 (5.2 g, 5%).

[0264] Step 162-2: Compound 162-1 (1.3 g, 8.67 mmol) and 3-bromopyridin-2-amine (0.5 g, 2.89 mmol) were dissolved in ethyl alcohol (10 mL), and two drops of sulfuric acid were added. The reaction solution was stirred at 90 °C for 21 hours. After completion of the reaction, the temperature was lowered to room temperature and filtered through diatomaceous earth (Celite). The filtrate was concentrated, diluted with ethyl acetate (20 mL), washed with 1 N aqueous sodium hydroxide and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated using column chromatography to obtain the target compound 162-2 (0.654 g, 84%).

[0265] Step 162-3: Compound 162-2 (3.4 g, 12.8 mmol) was dissolved in tetrahydrofuran (30 mL), and then sodium hydroxide (0.768 g, 19.2 mmol) dissolved in water (30 mL) was added and stirred for 3 hours. After completion of the reaction, the reaction solution was concentrated and acidified with 1N aqueous hydrochloric acid (pH ~2). After extraction with n-butanol (30 mL × 4), the mixture was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain the target compound 162-3 (3.532 g, 99.5%) as a hydrochloride salt.

[0266] Step 162-4: The target compound 162-4 was obtained by the same synthetic method as in Step 1-2 of Example 1 using the compound 162-3.

[0267] Step 162-5: Using compound 162-4, the target compound 162 was obtained by the same synthetic method as in Step 1-3 of Example 1. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.87(dd,J=7.0,1.2Hz,1H),8.29(t,J=1.9Hz,1H),8.03(d,J=7.5Hz,2H),7 .73(dd,J=7.2,1.2Hz,1H),7.65-7.43(m,2H),7.18(t,J=7.1Hz,1H),3.71(t,J=5.4Hz,4H),1.67-1.54(m, 6H). MS(ESI, LR) Calc. for C 19 H 19 ClNO[M+H] + :340.1,found:340.1.

[0268] Example 163 (8-(4-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] The target compound 163 was obtained by the same synthetic method as in steps 1-3 of Example 1 using compound 162-4 and 4-nitrophenylboronic acid. 1 H NMR(400MHz,DMSO)δ8.93(dd,J=7.0,1.2Hz,1H),8.50-8.41(m,2H),8.38(d,J=9.0Hz,2H),8.04(s,1H), 7.84(dd,J=7.2,1.2Hz,1H),7.24(t,J=7.1Hz,1H),3.71(t,J=5.4Hz,4H),1.65(dd,J=25.7,5.5Hz,6H). MS(ESI,LR) Calc. for C 19 H 19 N4O3[M+H] + :351.1,found:351.2.

[0269] Example 164 (8-(4-aminophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] Compound 163 was used to obtain target compound 164 in the same synthetic method as in Example 7. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.72(dd,J=6.8,1.2Hz,1H),7.95(s,1H),7.88(d,J=8.5Hz,2H),7.49(dd,J=7. 2,1.2Hz,1H),7.09(t,J=7.0Hz,1H),6.79-6.56(m,2H),5.37(s,2H),3.70(t,J=5.5Hz,4H),1.79-1.51(m,6H). MS(ESI,LR) Calc. for C 19 H 21 NO[M+H] + :321.2,found:321.2.

[0270] Example 165 (8-(3-chlorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] The target compound 165 was obtained by the synthesis method in Example 162 using 3-bromo-5-methyl-pyridin-2-amine and the corresponding compound. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.68(t,J=1.4Hz,1H),8.29(t,J=1.9Hz,1H),8.06(dt,J=7.6,1.6Hz,1H),7.95(s,1 H),7.64(d,J=1.6Hz,1H),7.58-7.45(m,2H),3.70(t,J=5.4Hz,4H),2.40(d,J=1.1Hz,3H),1.64(d,J=29.5Hz,6H). MS(ESI,LR) Calc. for C 20 H 21 ClNO[M+H] + :354.1,found:354.1.

[0271] Example 166 (8-(2-chloropyridin-4-yl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] The target compound 166 was obtained by the same synthetic method as in steps 1-3 of Example 1 using compound 165-2 and 3-chlorophenylboronic acid. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.75(t,J=1.4Hz,1H),8.54(d,J=5.3Hz,1H),8.44(d,J=1.6Hz,1H),8.23(dd,J=5. 3,1.6Hz,1H),7.99(s,1H),7.89(d,J=1.6Hz,1H),3.70(t,J=5.4Hz,4H),2.51(p,J=1.9Hz,3H),1.76-1.45(m,6H). MS(ESI,LR) Calc. for C 19 H 20ClNO[M+H] + :355.1,found:355.1.

[0272] Example 167 (8-(3-chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka] The target compound 167 was obtained by the synthesis method in Example 162 using 3-bromo-5-fluoro-pyridin-2-amine and the corresponding compound. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.93(dd,J=4.7,2.4Hz,1H),8.34(d,J=2.1Hz,1H),8.22-7.99(m,2H),7.9 1(dd,J=9.4,2.4Hz,1H),7.56(dd,J=4.9,2.3Hz,2H),3.70(t,J=5.4Hz,4H),1.64(dq,J=26.3,6.0Hz,6H). MS(ESI,LR) Calc. for C 19 H 18 ClFNO[M+H] + :358.1,found:358.1.

[0273] Example 168 (7-(4-methoxyphenyl)-[1,2,3]triazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone [ka]

[0274] Step 168-1: 2-Bromo-6-methyl-pyridine (3 g, 1.98 mmol) was dissolved in tetrahydrofuran (100 mL). The temperature was lowered to -78 °C, and lithium diisopropylamide (2 M solution, 17.44 mL, 34.88 mmol) was added and stirred for 10 minutes. N,N,N',N'-Tetramethylethylenediamine (TMEDA) (5.23 mL, 34.88 mmol) was added and stirred at the same temperature for 1 hour. Methyl chloroformate (2.7 mL, 34.88 mmol) was slowly added, and the temperature was raised to room temperature. After completion of the reaction, water (100 mL) was added, and the mixture was extracted with ethyl acetate (100 mL × 2). The combined organic layers were washed with brine. The mixture was dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was purified by column chromatography to give the target compound 168-1 (1.8 g, 45%).

[0275] Step 168-2 [Step 165-2]: Compound 168-1 (1.37 g, 5.95 mmol) and 4-acetamidobenzenesulfonyl azide (1.57 g, 6.5 mmol) were dissolved in acetonitrile (20 mL) and stirred. The temperature was lowered to 0 °C, and DBU (0.98 mL, 6.5 mmol) was added. The temperature was then raised to room temperature and stirred for 12 h. Upon completion of the reaction, saturated aqueous ammonium chloride (50 mL) was added and the mixture was filtered through diatomaceous earth (Celite). The filtrate was extracted with ethyl acetate (50 mL × 3). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The product was solidified with ethyl acetate / diethyl ether (1:10), filtered, and air-dried to give the target compound 168-2 (0.95 g, 62%). [DBU(1,8-Diazabicyclo(5,4,0)undec-7-ene)].

[0276] Steps 168-3, 168-4, and 168-5 [Steps 168-3, 168-4, and 168-5]: Compound 162-2 was used to obtain target compound 168 by the same synthetic method as in Steps 162-3, 162-4, and 162-5 in Example 162. 1H NMR(400MHz,DMSO-d6)δ(ppm):8.18(dd,J=8.8,1.2Hz,1H),8.10-7.95(m,2H),7.69(dd,J=8. 8,7.0Hz,1H),7.42(dd,J=7.1,1.2Hz,1H),7.27-7.11(m,2H),3.88(s,4H),1.79-1.50(m,6H). MS(ESI,LR) Calc. for C 19 H 21 N4NaO2[M+Na] + :359.2,found:359.2.

[0277] Example 169 (7-(3-chlorophenyl)-1H-indol-3-yl)(piperidin-1-yl)methanone [ka]

[0278] Step 169-1: 7-Bromoindole (0.5 g, 2.55 mmol) was dissolved in N,N-dimethylformamide (10 mL), trifluoroacetic anhydride (1.51 mL, 4.46 mmol) was added, and the mixture was stirred for 12 hours. After completion of the reaction, water was added, filtered, and washed with water. The resulting solid product was air-dried. The resulting solid product was dissolved in 4N aqueous sodium hydroxide (10 mL) and stirred at 100 °C for 2 hours. After completion of the reaction, the temperature was lowered to room temperature, and the mixture was acidified with hydrochloric acid (pH ~1), filtered, and washed with water. The resulting solid product was air-dried to obtain the target compound 169-1 (0.548 g, 78%) in the form of a hydrochloride salt.

[0279] Steps 169-2 and 169-3: Using compound 169-1, the target compound 169 was obtained by the same synthetic method as in Steps 162-4 and 162-5 in Example 162. 1H NMR(400MHz,DMSO-d6)δ(ppm):11.50(s,1H),7.71-7.63(m,2H),7.62-7.54(m,3H), 7.53-7.46(m,1H),7.28-7.13(m,2H),3.59(t,J=5.4Hz,4H),1.59(d,J=40.5Hz,6H). MS(ESI,LR) Calc. for C 20 H 20 ClNO[M+H] + :339.1,found:339.1.

[0280] Example 170 (6-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone Example 171. (6-(4-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0281] Examples 170 and 171 were obtained using methyl-6-bromopyrazolo[1,5-a]pyridine-3-carboxylate and the corresponding compounds in the same synthetic methods as in steps 162-3, 162-4, and 162-5 in Example 162. The structures and spectral data are shown in Table 37 below. [Table 37]

[0282] Example 172 (6-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone [ka] The target compound 172 was obtained by a synthetic method similar to that of steps 162-4 and 162-5 in Example 162 using 6-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid and the corresponding compound. 1 H NMR(400MHz,DMSO-d6)δ(ppm):12.96(d,J=7.3Hz,1H),8.93(t,J=2.6Hz,1H),8.45(d,J=7.2Hz,1H),7.46(d,J=1.9Hz,1H),7.3 1(dd,J=8.2,1.9Hz,1H),7.10(d,J=8.1Hz,1H),6.99(s,1H),6.12(s,2H),3.65(t,J=5.4Hz,4H),1.63(dt,J=30.8,5.8Hz,6H). MS(ESI,LR) Calc. for C 20 H 20 N3O3[M+H] + :350.2,found:350.2.

[0283] Example 173 (5-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone [ka] The target compound 173 was obtained by a synthetic method similar to that of steps 162-5, 162-3, and 162-4 in Example 162 using ethyl 5-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylate and the corresponding compound. 1H NMR(400MHz,DMSO-d6)δ(ppm):12.58(s,1H),8.20(d,J=8.6Hz,1H),7.88(d,J=8.7Hz,1H),7.65(d,J=1.9Hz,1H),7.59(dd,J=8 .2,1.9Hz,1H),7.13(d,J=8.2Hz,1H),6.92(d,J=2.0Hz,1H),6.15(s,2H),3.68(t,J=5.3Hz,4H),1.64(dq,J=29.9,5.7Hz,6H). MS(ESI,LR) Calc. for C 20 H 20 N3O3[M+H] + :350.2,found:350.2.

[0284] Example 174 (4-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-c]pyridin-2-yl)(piperidin-1-yl)methanone [ka] The target compound 174 was obtained by a synthetic method similar to that of steps 162-5, 162-3, and 162-4 in Example 162 using methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate and the corresponding compound. 1 H NMR(400MHz,DMSO-d6)δ(ppm):13.38(s,1H),8.40(d,J=6.7Hz,1H),7.84(d,J=6.7Hz,1H),7.61-7.51(m ,2H),7.28(d,J=9.1Hz,2H),6.24(s,2H),3.68(s,3H),1.66(d,J=7.0Hz,2H),1.58(s,3H),1.25(s,1H). MS(ESI,LR) Calc. for C 20 H 20 N3O3[M+H] + :350.2,found:350.2.

[0285] Example 175 (4-(benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[2,3-c]pyridin-2-yl)(piperidin-1-yl)methanone [ka] Using ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate and the corresponding compound, the target compound 175 was obtained by a synthetic method similar to that of steps 162-5, 162-3, and 162-4 in Example 162. 1 H NMR(400MHz,DMSO-d6)δ(ppm):13.73(s,1H),9.15(s,1H),8.45(s,1H),7.41(d,J=1.8Hz,1H),7 .33(dd,J=8.0,1.9Hz,1H),7.14(d,J=8.1Hz,2H),6.15(s,2H),3.66(s,4H),1.77-1.45(m,6H). MS(ESI,LR) Calc. for C 20 H 20 N3O3[M+H] + :350.2,found:350.2.

[0286] Example 176 (4-(benzo[d][1,3]dioxol-5-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl)(piperidin-1-yl)methanone [ka] The target compound 176 was obtained by a synthetic method similar to that of steps 162-5, 162-3, and 162-4 in Example 162 using ethyl 4-chloropyrrolo[2,1-f][1,2,4]culiadin-6-carboxylate and the corresponding compound. 1 H NMR(400MHz,DMSO-d6)δ(ppm):8.64(s,1H),8.32(d,J=1.5Hz,1H),7.80(dd,J=8.2,1.8Hz,1H),7.66(d,J= 1.8Hz,1H), 7.28(d,J=1.6Hz,1H),7.14(d,J=8.2Hz,1H),6.19(s,2H),1.64(t,J=6.3Hz,2H),1.54(s,3H). MS(ESI,LR) Calc. for C 19 H 19 N4O3[M+H] + :351.1,found:351.1.

[0287] Example 177 (4-(benzo[d][1,3]dioxol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)(piperidin-1-yl)methanone [ka] The target compound 177 was obtained by a synthetic method similar to that of steps 162-4 and 162-5 in Example 162 using 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid and the corresponding compound. 1H NMR(400MHz,DMSO-d6)δ(ppm):12.97(s,1H),8.91(s,1H),7.76(dd,J=8.1,1.8Hz,1H),7.69(d,J=1.8Hz,1H),7.16(d,J =8.2Hz,1H),7.12(s,1H),6.18(s,2H),3.64(t,J=5.4Hz,4H),1.66(s,2H),1.57(s,3H),1.24(s,2H),0.89-0.82(m,1H). MS(ESI,LR) Calc. for C 19 H 19 N4O3[M+H] + :351.1,found:351.1.

[0288] Example 178 (5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 179. (5-(4-methoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 180 (5-(4-chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 181 (5-(3,4-dimethoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 182 (5-(4-fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 183 (5-(furaN-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 184. Piperidin-1-yl(5-(pyridin-4-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)methanone Example 185 (5-(3-chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 186 (5-(3-chloro-4-hydroxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 187 (2-(benzo[d][1,3]dioxol-5-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)(piperidin-1-yl)methanone Example 188 (5-(benzofuran-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 189 (5-(naphthalen-2-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 190 (5-(1H-indazol-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone Example 191. 2-(2-(piperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)isoindolin-1-one

[0289] Examples 178, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, and 191 were obtained using ethyl 5-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylate and the corresponding compounds in the same synthetic manner as in steps 162-3, 162-4, and 162-5 in Example 162. The structures and spectral data are shown in Table 38 below. [Table 38-1] [Table 38-2]

[0290] Example 413. 3-Hydroxy-5-[2-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-6-yl]pyridine-2-carbonitrile [ka]

[0291] Step 413-1: Using 6-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid, the target compound 413-1 was obtained by the same synthetic method as in Step 1-2 of Example 1.

[0292] Step 413-2: Using compound 413-1, the target compound 413 was obtained by the same synthetic method as in Step 159-3 in Example 159. 1 H NMR(400MHz,DMSO-d6)δ(ppm):9.23(s,1H),8.62(d,J=1.9Hz,1H),7.88(d,J=9.3Hz,1H),7.68(d,J=1.9Hz,1H),7. 62(dd,J=9.3,1.7Hz,1H),6.89(s,1H),3.67(dt,J=16.9,5.1Hz,4H),1.65(q,J=6.1Hz,2H),1.55(d,J=22.3Hz,4H). MS(ESI,LR) Calc. for C 19 H 18 NO2[M+H] + :348.1,found:348.1.

[0293] Experimental Example 1. Evaluation of 15-PGDH inhibitory activity The 15-PGDH inhibitory activity of the compounds of the examples was measured as follows. 6.7 ng of human 15-PGDH (R&D System #5660-DH) enzyme (10 μL) was added to a black 96-well plate, followed by 60 μL of buffer (50 mM Tris-HCl, pH 7.5, 0.01% Tween 20) and 10 μL of 200 μM β-nicotinamide adenine dinucleotide sodium salt (Sigma, Cat# N0632-5G). 10 μL (10x) of compound solution in DMSO was added, and the mixture was incubated at room temperature for 10 minutes. Then, 10 μL of 200 μM prostaglandin E2 was added, and readings were taken at ex (λ360 nm) / em (λ450 nm) intervals of 30 seconds for 30 minutes. The resulting value, V max (milliunit per min) was obtained. V max The slope, i.e., the linear section, was determined and defined as 0% inhibition for enzyme alone and 100% inhibition for substrate alone, and each compound was converted into a concentration-specific % inhibition potency using Equation 1. The results were analyzed by nonlinear regression using Prism to determine the concentration IC at which 50% inhibition was observed in the concentration-response curve of the test compound. 50 asked for.

number

[0294] Experimental Example 2. Measurement of PGE2 Increasing Ability in A549 Cells A549 cells were prepared in F12K medium containing 10% FBS (Fetal Bovine Serum) at a cell density of 1×10 5 / mL. After treating each well of a 96-well cell culture plate with 2×10 4 / 200 μL, the cells were cultured in a 37°C, 5% CO2 incubator for 24 hours. After the culture was completed, all the F12K medium was removed, and the wells were washed once with 100 μL of PBS. Then, 160 μL of serum-free F12K medium was added to each well. Subsequently, wells treated with IL-1β were treated with 20 μL of IL-1β diluted to 10-fold concentration of 1 ng / mL in serum-free F12K medium, and wells not treated with IL-1β were treated with 20 μL of serum-free F12K medium. Wells treated with the compound were treated with 20 μL of the compound dissolved in 100% DMSO and diluted to 10-fold concentration of the desired compound concentration in serum-free F12K medium so that the final DMSO concentration in the cells was 0.1%. Wells not treated with the compound were treated with 20 μL of DMSO diluted in serum-free F12K medium so that the final DMSO concentration in the cells was 0.1%. To confirm the increase or decrease in the amount of PGE2 secreted in the supernatant collected after culturing in a 37°C, 5% CO2 incubator for 24 hours, PGE2 was quantified using the Prostaglandin E2 Parameter (SKGE004B).

[0295] As a result, as shown in Table 39 below, it was confirmed that the amount of PGE2 increased due to the inhibition of 15-PGDH activity at a concentration of 1 μM of each compound (0 < PGE2 increasing ability < 1.5: +, PGE2 increasing ability ≥ 1.5: ++).

Table 39-1

Table 39-2

Table 39-3

[0296] The above description of the present invention is for illustrative purposes only, and those skilled in the art will understand that the present invention can be easily modified into other specific forms without changing the technical spirit or essential features of the present invention. Therefore, it should be understood that the above-described embodiments are illustrative in all respects and are not limiting. For example, each component described as a single type can be implemented in a distributed form, and similarly, each component described as a distributed type can be implemented in a combined form.

[0297] The scope of the present invention is defined by the following claims, and all changes and modifications that fall within the meaning and scope of the claims and their equivalents should be construed as being included within the scope of the claims.

Claims

1. A heterocyclic compound represented by the following chemical formula 1, a hydrate thereof, a solvate thereof or a pharmaceutically acceptable salt thereof: 【Chemistry 1】 In the above formula, Ring A and ring B are fused to form a fused ring of two rings, X １ , Y １ , Y ２ , Y ３ and Y ４ are independently CH or N; X ２ is CH, N or NH, Z １ and Z ２ is C or N, X １ , X ２ , Y １ , Y ２ , Y ３ , Y ４ , Z １ and Z ２ at least one of is N or NH; R ａ is H, R ａ－１ C replaced by １－６ Straight or branched chain alkyl, or C(O)R ａ－１ and The R ａ－１ is C １－６ Straight or branched chain alkyl, C ３－８ Cycloalkyl, hydroxy, R ｓ or R ｕ and R ａ－１ represents one or more independent R ａ－２ or not replaced by, The R ａ－２ is C １－６ Straight or branched alkyl, halogen, C １－４ is haloalkyl, The X １ is R ｂ is substituted or unsubstituted, and ｂ is amino or C(O)R ｓ and The Y １ is R １ is substituted or unsubstituted, and １ is R ｆ and The Y ２ is R ２ or not replaced by, The R ２ is C １－６ Straight or branched alkyl, halogen, C ５－１２ a monocyclic or bicyclic aryl of the formula R ｕ or R ｆ and R ２ represents one or more independent R ２－１ or not replaced by, The R ２－１ is C １－４ alkoxy, halogen or hydroxy; The Y ３ is R ３ or not replaced by, The R ３ is C ５－７ Aryl, R ｕ or R ｆ and R ３ represents one or more independent R ３－１ or not replaced by, The R ３－１ is C １－４ alkoxy, halogen, hydroxy or cyano; The Y ４ is R ４ or -L-R ４ or not replaced by, The L is —NH(CH ２ ) ｍ -, -NHC(O)-, -NHSO ２ - or -S-, wherein m is an integer of 0 to 3; The R ４ is C ５－１２ a monocyclic or bicyclic aryl of the formula R ｕ , R ｓ or R ｆ and R ４ is unsubstituted or substituted independently by one or more Q; The Q is 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 , C.H. ２ R ５ , N.R. ５ R ６ , C(O)R ５ , C(O)OR ５ , C(O)NR ５ R ６ ,NHC(O)(CH ２ ) ｐ R ５ , NHC(O)CH ２ OR ５ , NHC(O)CH ２ NR ５ R ６ , NHCH ２ CH ２ R ５ , N.R. ５ C(O)R ６ , R ｕ or R ｓ wherein p is an integer of 0 to 3, and Q is one or more independent R ７ or not replaced by, The R ５ and R ６ are independently 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 and The R ７ is 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 , R ｕ C replaced by １－４ Alkyl or R ｓ and Q and R ７ The bond to is a single bond or a double bond, The R ｓ is a 4-10 membered mono- or bicyclic saturated heterocycloalkyl ring containing 1 to 3 heteroatoms selected from N, O and S; The R ｕ is a 5-7 membered unsaturated heterocycloalkyl ring containing 1 to 4 heteroatoms selected from N, O and S; The R ｆ is a fused ring of two rings in which a 5- to 7-membered saturated or unsaturated heterocycloalkyl ring containing 1 to 2 heteroatoms selected from N, O, and S is fused with an aryl ring or a 5- to 7-membered heteroaryl ring containing 1 to 2 N atoms, The R ｓ , R ｕ and R ｆ is independently substituted with 1 to 2 oxo (O) or thioxo (S), or is unsubstituted.

2. The compound according to claim 1, or a hydrate, solvate or pharmaceutically acceptable salt thereof, wherein the A ring is pyrrole, pyrazole, imidazole or triazole.

3. The compound according to claim 1, or a hydrate, solvate or pharmaceutically acceptable salt thereof, wherein the B ring is benzene, pyridine, pyrimidine or triazine.

4. The compound according to claim 1, its hydrate, its solvate or its pharmaceutically acceptable salt, characterized in that the two fused rings formed by condensing ring A and ring B are indole, indazole, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, pyrazolopyridine, imidazopyridine or triazolopyridine.

5. The compound according to claim 1, its hydrate, its solvate or its pharmaceutically acceptable salt, characterized in that the two fused rings formed by the fusion of ring A and ring B are any one selected from the group consisting of the following chemical formulas: 【Chemistry 2】

6. The R ａ H, propyl, C(O)R ａ－１ and The R ａ－１ is methyl, butyl, cyclohexyl, hydroxy, piperidinyl, azaspiroheptanyl, azaspirooctanyl, azaspirononanyl, azabicycloheptanyl, azabicyclooctanyl, azabicyclononanyl, or tetrahydropyridinyl; The R ａ－２ The compound according to claim 1, or a hydrate, solvate or pharmaceutically acceptable salt thereof, wherein is methyl, ethyl, propyl, isopropyl, fluoro or trifluoromethyl.

7. The R ｂ The compound according to claim 1, or a hydrate, solvate or pharmaceutically acceptable salt thereof, wherein is amino or piperidinyl-carbonyl.

8. The R １ The compound according to claim 1, or a hydrate, solvate or pharmaceutically acceptable salt thereof, wherein is benzodioxolyl.

9. The R ２ is methyl, fluoro, phenyl, naphthyl (naphthalenyl), furanyl, pyridinyl, isoindolinone, benzodioxolyl, dihydrobenzodioxinyl, benzofuranyl, or indazolyl; The R ２－１ The compound according to claim 1, or a hydrate, solvate or pharmaceutically acceptable salt thereof, wherein is methoxy, chloro, fluoro or hydroxy.

10. The R ３ is phenyl, pyridinyl or benzodioxolyl; The R ３－１ The compound according to claim 1, or a hydrate, solvate or pharmaceutically acceptable salt thereof, wherein is methoxy, chloro, hydroxy or cyano.

11. The L is -NH-, -NHCH ２ -, -NH(CH ２ ) ２ -, -NHC(O)-, -NHSO ２ 2. The compound according to claim 1, or a hydrate, solvate or pharmaceutically acceptable salt thereof, wherein R is - or -S-.

12. The 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, benzisoxazolone, dihydronaphthyridinone, benzoxazolyl, benzisoxazolyl, triazolopyridinone, phthalazinone, quinazolinone, or pyridopyrimidinone, or a hydrate, solvate, or pharmaceutically acceptable salt thereof according to claim 1 .

13. wherein Q is methyl, propyl, isopropyl, fluoro, chloro, bromo, hydroxy, trifluoromethyl, methoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR ５ , C.H. ２ R ５ , N.R. ５ R ６ , C(O)R ５ , C(O)OR ５ , C(O)NR ５ R ６ , NHC(O)R ５ , NHC(O)CH ２ R ５ ,NHC(O)(CH ２ ) ２ R ５ , NHC(O)CH ２ OR ５ , NHC(O)CH ２ NR ５ R ６ , NHCH ２ CH ２ R ５ , N.R. ５ C(O)R ６ , tetrazolyl, oxadiazolyl, oxadiazolone, furyl, thienyl, imidazolyl, pyrazolyl, isoxazolyl, thiazolyl, oxo-thiadiazolyl, thioxo-oxadiazolyl, pyridinyl, pyrimidinyl, azetidinyl, oxazolidinone, piperidinyl, piperazinyl, morpholino, azaspiroheptanyl, azaspirooctanyl, azaspirononanyl, azabicycloheptanyl or azabicyclooctanyl, The R ５ is H, methyl, ethyl, butyl, cyclopropyl, cyclohexane, methoxy, amino, phenyl, benzyl, imidazolyl, oxadiazolyl, oxadiazolone, pyridinyl, pyrimidinyl, azetidinyl, piperidinyl, piperidinone, piperazinyl, morpholino, thiazolidinedione, piperazinone, piperazine-dione, azaspiroheptanyl or azaspirononanyl, The R ６ The compound according to claim 1, its hydrate, its solvate or its pharmaceutically acceptable salt, characterized in that: is H, methyl, ethyl, propyl, isopropyl, sulfonyl, pyrazolyl, pyridinyl, pyridazinyl, azetidinyl or piperidinyl.

14. The R ７ The compound according to claim 1, or a hydrate, solvate, or pharmaceutically acceptable salt thereof, wherein is methyl, propyl, isopropyl, cyclopropyl, fluoro, chloro, difluoromethyl, trifluoromethyl, hydroxy, methoxy, hydroxymethyl, cyano, amino, dimethylamino, methylcarboxylate, tert-butylcarboxylate, nitro, isoxazolyl, thiazolyl, pyridinyl, or oxadiazolylmethyl.

15. The compound of claim 1, its hydrate, its solvate, or its pharmaceutically acceptable salt, wherein the compound represented by Chemical Formula 1 is any one selected from the group consisting of the following compounds: [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-(piperidine-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-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [43] (7-(5-(2-azaspiro[3,3]heptane-2-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [44] (3,3-difluoroazetidin-1-yl)(5-(3-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide, [48] ​​piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone, [49] (4-methylpiperazin-1-yl)(5-(3-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)nicotinamide, [54] 5-(3-(piperidine-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-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [87] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)picolinamide, [88] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)picolinamide, [89] N-(isoxazol-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide, [90] N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)furan-2-carboxamide, [91] 3-methoxy-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide, [92] 1-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)urea, [93] 1-methyl-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide, [94] N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)piperidine-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-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [142] 2-isopropyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [143] 5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [144] 2-methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [145] 6-(3-(piperidine-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-(piperidine-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-(piperidine-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-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)piperidine-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-(piperidine-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]pyridine-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-difluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [210] (7-(6-(3-hydroxyazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [211] 7-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino 3,4-dihydro-2H-isoquinolin-1-one, [212] 6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]isoindolin-1-one, [213] (3-fluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone, [214] 2-azaspiro[3,3]heptan-2-yl-[5-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone, [215] (7-(6-(2-azabicyclo[2.2.1]heptan-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [216] (7-(6-(2-azabicyclo[2.2.2]octan-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [217] (7-(6-(7-azabicyclo[2.2.1]heptan-7-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [218] (7-(6-(3-(dimethylamino)azetidin-1-yl)(pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [219] methyl 1-(5-(3-(piperidine-1-carbonyl)(pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)azetidine-3-carboxylate, [220] (7-(6-(2-azaspiro[3.3]heptan-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [221] (7-(6-(3-(hydroxymethyl)azetidin-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]octan-6-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [224] 7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-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-(piperidine-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-fluoropiperidine-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]pyrazolo-4-sulfonamide, [241] 5-fluoro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-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-(piperidine-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]pyridine-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-(piperidine-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-(piperidine-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-hydroxypyrimidin-5-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidyl)methanone, [307] 5-[4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carboxamide, [308] 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide, [312] 3-nitro-5-(3-(piperidine-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-chloropyridin-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-(piperidine-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-(piperidine-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-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-1H-imidazole-5-carboxamide, [334] N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)pyrimidine-5-carboxamide, [335] 5-fluoro-N-(5-(3-(piperidine-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-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-(trifluoromethyl)piperidin-1-yl)methanone, [339] 3-(5-(3-(3-(trifluoromethyl)piperidine-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-ethylpiperidine-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-3H-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]octane-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-ethylpiperidine-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-piperidine-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-isopropylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [401] 6-(3-(1,2,3,6-tetrahydropyridine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [402] 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide, [403] N-(5-(3-piperidine-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-hydro-5-[2-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-6-yl]pyridine-2-carbonitrile.

16. A pharmaceutical composition for preventing or treating a 15-PGDH-associated disease, comprising the heterocyclic compound, its hydrate, its solvate, or its pharmaceutically acceptable salt according to any one of claims 1 to 15 as an active ingredient.

17. The 15-PGDH-associated diseases include inflammatory diseases (inflammatory bowel diseases (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 (NSAIDs-induced ulcer), vascular inflammation syndrome, non-alcoholic steatohepatitis (NASH), atopic dermatitis, psoriasis, interstitial cystitis, prostatitis syndrome), fibrosis (pulmonary fibrosis (idiopathic pulmonary fibrosis)), renal fibrosis (glomerular fibrosis)), and the like. fibrosis), cardiac fibrosis (myocardial fibrosis), oral fibrosis, deltoid muscle fibrosis, liver fibrosis, myelofibrosis, scleroderma), autoimmune diseases (systemic lupus erythematosus, rheumatoid arthritis, autoimmune hepatitis, severe combined immunodeficiency syndrome (SCID)), ophthalmological diseases (xerophthalmia, conjunctivitis, keratitis), thrombocytopenia (drug-induced thrombocytopenia, autoimmune thrombocytopenia, idiopathic thrombocytopenia, thrombocytopenia due to viral infection), muscle diseases (muscle atrophy, muscle damage, muscular dystrophy) ), anemia (aplastic anemia, anemia of chronic disease, Fanconi anemia, β-thalassemia or anemia of unknown cause), cardiovascular disease (heart disease (angina pectoris, heart failure, myocardial infarction), kidney disease (chronic kidney disease, renal failure), stroke, pulmonary hypertension, peripheral circulatory disorder), neuronal cell death (neuropsychiatric disorders, neurodegenerative diseases, nerve damage), cytopenia (immune cytopenia, neutropenia, lymphopenia), osteoporosis, fractures, leukemia (acute myeloid leukemia (AML), acute lymphocytic leukemia (ALL), chronic myeloid leukemia (CML)), lymphoma (Hodgkin's lymphoma, non-Hodgkin's lymphoma), toxicity due to radiation exposure, 15-PGDH expression 17. The pharmaceutical composition according to claim 16, wherein the disease is one or more selected from the group consisting of current cancer, multiple myeloma, paroxysmal nocturnal hemoglobinuria (PNH), pure red cell aplasia, megakaryocytosis, Wiskott-Aldrich syndrome, sickle cell disease, Hurler syndrome, adrenoleukodystrophy, metachromatic leukodystrophy, myelodysplasia, Duchenne muscular dystrophy, solid tumors, chronic granulomatous disease, systemic sclerosis, scars, wounds, ear 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 disease.

18. A pharmaceutical composition comprising the heterocyclic compound, its hydrate, its solvate or its pharmaceutically acceptable salt according to any one of claims 1 to 15, and a pharmaceutically acceptable excipient.

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