Novel heterocyclic compound

Abstract

The present invention provides a novel heterocyclic compound as a 15-PGDH inhibitor, or a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof. The novel heterocyclic compound of the present invention demonstrates excellent 15-PGDH inhibitory activity, and thus has been found to be useful in the prevention or treatment of 15-PGDH-related diseases. Therefore, the novel heterocyclic compound according to the present invention can be effectively used in the prevention or treatment of 15-PGDH-related diseases in the field of medicine and pharmacy.

Description

Technical Field

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

[0002] Prostaglandins are physiologically active substances synthesized in vivo, are widely distributed in organs and body fluids, and bring into play physiological functions in small quantities.Prostaglandins are fatty acid derivatives consisting of 20 carbons, and have the basic skeleton of prostatic acid (prostanicacid), have 5-membered rings at the center of molecular structure. According to the formula difference of the 5-membered ring, it is divided into A group to J group, and according to the number of double bonds in two side chains, it is divided into series 1 to series 3. They are widely present in animal tissues, and are known to be rapidly metabolized after being synthesized by polyunsaturated fatty acids. These prostaglandins can stimulate smooth muscle contraction according to their form, and in some animals, they reduce or increase blood pressure, reduce or increase blood coagulation, and they are also known to promote ion transport on the film, stimulate inflammation, and suppress cardiovascular disease and viral infection.

[0003] 15-PGDH (15-hydroxyprostaglandin dehydrogenase) uses active prostaglandins such as PGD2, PGE1, PGE2, PGF2α and PGI2 as substrates and participates in the inactivation of these active prostaglandins, such as conversion into 15-keto-PGE2, which catalyzes the oxidation reaction of the hydroxyl group at position 15 of PGE2.

[0004] The receptors corresponding to 15-PGDH substrates are widely distributed in the body, have different expression sites, and are known to be involved in various physiological functions in the body. For example, substrates of 15-PGDH include substrates with anti-fibrotic effects, anti-inflammatory effects, blood circulation improvement effects, proliferation promotion effects, stem cell increase promotion effects, smooth muscle contraction / relaxation effects, immunosuppressive effects, and bone metabolism effects. Therefore, 15-PGDH inhibitors can be effectively used to treat or prevent diseases such as fibrosis [pulmonary fibrosis (such as idiopathic pulmonary fibrosis)], liver fibrosis, renal fibrosis, myocardial fibrosis, scleroderma, myelofibrosis, etc.], inflammatory diseases [chronic obstructive pulmonary disease (COPD), acute lung injury, sepsis, asthma and exacerbation of lung diseases, inflammatory bowel disease (ulcerative colitis, Crohn's disease, etc.), peptic ulcers (such as NSAID-induced ulcers), autoinflammatory diseases (such as Behcet's disease (Behcet's disease) disease), vasculitis syndrome, acute liver injury, acute kidney injury, non-alcoholic fatty liver disease (NASH), atopic dermatitis, psoriasis, interstitial cystitis, prostatitis syndrome (such as chronic prostatitis / chronic pelvic pain syndrome)], circulatory 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, bedsores, acute mucosal injuries including Stevens-Johnson syndrome, anticancer chemotherapy, immunotherapy or radiotherapy, mucosal injuries associated with graft-versus-host disease (mucositis or stomatitis), etc.], autoimmune diseases [multiple sclerosis, rheumatoid arthritis, etc.], graft-versus-host disease (GVHD), hair loss, osteoporosis, ear diseases [hearing loss, tinnitus, vertigo, balance disorders, etc.], eye diseases [glaucoma, dry eye, etc.], diabetes, underactive bladder bladder), neutropenia, promotion of engraftment in stem cell and bone marrow transplantation or organ transplantation, neurogenesis and neural cell death [psychiatric disorders, neural injury, neurotoxic disorders, neuropathic pain, neurodegeneration], muscle regeneration [muscular dystrophy, muscle injury] and cervical ripening. Detailed Description of the Invention

[0006] Purpose of the Invention

[0007] The problem to be solved by the present invention is to provide a novel 15-PGDH inhibitory compound having a structure showing excellent 15-PGDH inhibitory activity.

[0008] Furthermore, the problem to be solved by the present invention is to provide a pharmaceutical composition for preventing or treating 15-PGDH-related diseases, which comprises a 15-PGDH inhibitory compound having a novel structure.

[0009] Furthermore, the present invention aims to provide a method for preventing or treating 15-PGDH-related diseases, which comprises administering a therapeutically effective amount of a 15-PGDH inhibitory compound having a novel structure to a subject in need thereof.

[0010] In addition, the problem to be solved by the present invention is to provide a novel 15-PGDH inhibitory compound with a novel structure for use as an active ingredient in the preparation of a drug for preventing or treating 15-PGDH-related diseases.

[0011] The problems to be solved by the present invention are not limited to the above problems, and ordinary technicians in the technical field to which the present invention belongs can clearly understand other technical problems not mentioned from the following description.

[0012] Solution to the problem

[0013] In order to solve the above problems, according to one aspect of the present invention, there is provided a heterocyclic compound represented by the following Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof:

[0014] <Formula 1>

[0015]

[0016] in,

[0017] forming a fused bicyclic ring of rings A and B,

[0018] X1, Y1, Y2, Y3 and Y4 are independently CH or N,

[0019] X2 is CH, N or NH,

[0020] Z1 and Z2 are C or N,

[0021] At least one of X1, X2, Y1, Y2, Y3, Y4, Z1 and Z2 is N or NH,

[0022] R a It is H, R a-1 Substituted C 1-6 Straight chain or branched alkyl, or C(O)R a-1 ,

[0023] R a-1 It is C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, hydroxyl, R s or R u , and R a-1 Optionally, one or more independent R a-2 replace,

[0024] R a-2 It is C 1-6 Straight-chain or branched alkyl, halogen, C 1-4 haloalkyl,

[0025] X1 is optionally b Substituted, where R b is amino or C(O)R s ,

[0026] Y1 is optionally substituted by R 1 Replacement, R 1 It is R f ,

[0027] Y2 is optionally 2 replace,

[0028] R 2 It is C 1-6 Straight or branched alkyl, halogen, C 5-12 Aryl, R u or R f , and R 2 Optionally, one or more independent R 2-1 replace,

[0029] R 2-1 It is C 1-4 alkoxy, halogen or hydroxy,

[0030] Y3 is optionally 3 replace,

[0031] R 3 It is C 5-7 Aryl, R u or R f , and R 3 Optionally, one or more independent R 3-1 replace,

[0032] R 3-1 It is C 1-4 alkoxy, halogen, hydroxy or cyano,

[0033] Y4 is optionally 4 or -LR 4 replace,

[0034] L is -NH(CH2) m -, -NHC(O)-, -NHSO2- or -S-, m is an integer from 0 to 3,

[0035] R 4 It is a C with 1 to 2 rings 5-12 Aryl, R u 、Rs or R f , and R 4 is optionally substituted with one or more than one independent Q,

[0036] Q is C 1-6 Straight-chain or branched alkyl, halogen, hydroxyl, C 1-4 Halogenated alkyl, C 1-4 Alkoxy, nitro, cyano, amino, carboxylate, carboxylic acid, CHR 5 、CH2R 5 NR 5 R 6 、C(O)R 5 、C(O)OR 5 、C(O)NR 5 R 6 、NHC(O)(CH2) p R 5 、NHC(O)CH2OR 5 、NHC(O)CH2NR 5 R 6 、NHCH2CH2R 5 NR 5 C(O)R 6 、R u or R s , p is an integer from 0 to 3, and Q is optionally substituted by one or more independent R 7 replace,

[0037] R 5 and R 6 Independently H, C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, C 1-4 Alkoxy, amino, sulfonyl, C 5-7 Aryl, arylalkyl, R u or R s ,

[0038] R 7 It is C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, halogen, C 1-4 Haloalkyl, hydroxy, C 1-4 Alkoxy, hydroxyalkyl, cyano, amino, alkylamino, C 1-6 Alkyl carboxylate group, nitro group, R u 、 u Substituted C 1-4 Alkyl or R s , and Q and R 7The bond between them is a single bond or a double bond,

[0039] R s is a 4- to 10-membered saturated heterocycloalkyl ring having 1 to 2 rings, which has 1 to 3 heteroatoms selected from N, O and S,

[0040] R u is a 5- to 7-membered unsaturated heterocycloalkyl ring having 1 to 4 heteroatoms selected from N, O and S,

[0041] R f is a fused bicyclic ring in which a 5- to 7-membered saturated or unsaturated heterocycloalkyl ring having 1 to 2 heteroatoms selected from N, O and S is fused to an aryl ring or a 5- to 7-membered heteroaryl ring having 1 to 2 N,

[0042] R s 、R u and R f Independently, optionally substituted with one to two oxo (O) or thioxo (S) groups.

[0043] According to another aspect of the present invention, provided is a pharmaceutical composition for preventing or treating 15-PGDH-related diseases, comprising as an active ingredient a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

[0044] According to another aspect of the present invention, a method for preventing or treating a 15-PGDH-related disease is provided, which comprises administering to a subject in need thereof a therapeutically effective amount of a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

[0045] According to another aspect of the present invention, provided is a use of a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof as an active ingredient in the preparation of a medicament for preventing or treating 15-PGDH-related diseases.

[0046] According to another aspect of the present invention, provided is a pharmaceutical composition comprising a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive.

[0047] Effects of the Invention

[0048] The novel heterocyclic compounds of the present invention have been demonstrated to exhibit excellent 15-PGDH inhibitory activity and, therefore, have been found to be useful for preventing or treating 15-PGDH-related diseases.

[0049] Therefore, in the fields of medicine and pharmacy, the novel heterocyclic compounds of the present invention can be effectively used to prevent or treat 15-PGDH-related diseases.

[0050] The effects of the present invention are not limited to the above-described effects, and should be understood to include all effects that can be inferred from the constitution of the present invention described in the specification or claims of the present invention.

[0051] Inventing the best model

[0052] The present invention provides a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof:

[0053] <Formula 1>

[0054]

[0055] in,

[0056] forming a fused bicyclic ring of rings A and B,

[0057] X1, Y1, Y2, Y3 and Y4 are independently CH or N,

[0058] X2 is CH, N or NH,

[0059] Z1 and Z2 are C or N,

[0060] At least one of X1, X2, Y1, Y2, Y3, Y4, Z1 and Z2 is N or NH,

[0061] R a It is H, R a-1 Substituted C 1-6 Straight chain or branched alkyl, or C(O)R a-1 ,

[0062] R a-1 It is C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, hydroxyl, R s or R u , and R a-1 Optionally, one or more independent R a-2 replace,

[0063] R a-2 It is C 1-6 Straight-chain or branched alkyl, halogen, C 1-4 haloalkyl,

[0064] X1 is optionally b Substituted, where R b is amino or C(O)R s ,

[0065] Y1 is optionally substituted by R 1 Replacement, R 1 It is R f ,

[0066] Y2 is optionally 2 replace,

[0067] R 2 It is C 1-6 Straight or branched alkyl, halogen, C 5-12 Aryl, R u or R f , and R 2 Optionally, one or more independent R 2-1 replace,

[0068] R 2-1 It is C 1-4 alkoxy, halogen or hydroxy,

[0069] Y3 is optionally 3 replace,

[0070] R 3 It is C 5-7 Aryl, R u or R f , and R 3 Optionally, one or more independent R 3-1 replace,

[0071] R 3-1 It is C 1-4 alkoxy, halogen, hydroxy or cyano,

[0072] Y4 is optionally 4 or -LR 4 replace,

[0073] L is -NH(CH2) m -, -NHC(O)-, -NHSO2- or -S-, m is an integer from 0 to 3,

[0074] R 4 It is a C with 1 to 2 rings 5-12 Aryl, R u 、R s or R f , and R 4 is optionally substituted with one or more than one independent Q,

[0075] Q is C 1-6 Straight-chain or branched alkyl, halogen, hydroxyl, C 1-4 Halogenated alkyl, C 1-4Alkoxy, nitro, cyano, amino, carboxylate, carboxyl, CHR 5 、CH2R 5 NR 5 R 6 、C(O)R 5 、C(O)OR 5 、C(O)NR 5 R 6 、NHC(O)(CH2) p R 5 、NHC(O)CH2OR 5 、NHC(O)CH2NR 5 R 6 、NHCH2CH2R 5 NR 5 C(O)R 6 、R u or R s , p is an integer from 0 to 3, and Q is optionally substituted by one or more independent R 7 replace,

[0076] R 5 and R 6 Independently H, C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, C 1-4 Alkoxy, amino, sulfonyl, C 5-7 Aryl, arylalkyl, R u or R s ,

[0077] R 7 It is C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, halogen, C 1-4 Haloalkyl, hydroxy, C 1-4 Alkoxy, hydroxyalkyl, cyano, amino, alkylamino, C 1-6 Alkyl carboxylate group, nitro group, R u 、 u Substituted C 1-4 Alkyl or R s , and Q and R 7 The bond between them is a single bond or a double bond,

[0078] R s is a 4- to 10-membered saturated heterocycloalkyl ring having 1 to 2 rings, which has 1 to 3 heteroatoms selected from N, O and S,

[0079] R u is a 5- to 7-membered unsaturated heterocycloalkyl ring having 1 to 4 heteroatoms selected from N, O and S,

[0080] R f is a fused bicyclic ring in which a 5- to 7-membered saturated or unsaturated heterocycloalkyl ring having 1 to 2 heteroatoms selected from N, O and S is fused to an aryl ring or a 5- to 7-membered heteroaryl ring having 1 to 2 N atoms,

[0081] R s 、R u and R f are independently optionally substituted with one to two oxy (O) or sulfydene (S) groups.

[0082] In one embodiment, the A ring can be pyrrole, pyrazole, imidazole, or triazole, and the B ring can be benzene, pyridine, pyrimidine, or triazine.

[0083] In one embodiment, the fused bicyclic ring of ring A and ring B can be indole, indazole, pyrrolopyridine, pyrrolopyrimidine, pyrrolotriazine, pyrazolopyridine, imidazopyridine or triazolopyridine. More specifically, the fused bicyclic ring of ring A and ring B can be one selected from the following:

[0084]

[0085] In one embodiment, R a Can be H, propyl, C(O)R a-1 , R a-1 can be methyl, butyl, cyclohexyl, hydroxy, piperidinyl, azaspiroheptyl, azaspirooctyl, azaspironanyl, azabicycloheptyl, azabicyclooctyl, azabicyclononanyl or tetrahydropyridinyl, and R a-2 It may be methyl, ethyl, propyl, isopropyl, fluoro or trifluoromethyl.

[0086] In one embodiment, R b It may be amino or piperidinyl-carbonyl.

[0087] In one embodiment, R 1 It may be benzodioxolyl.

[0088] In one embodiment, R 2 can be methyl, fluoro, phenyl, naphthyl (naphthalenyl)), furyl, pyridyl, isoindolinone, benzodioxolyl, dihydrobenzodioxinyl, benzofuranyl or indazolyl, and R 2-1 It may be methoxy, chloro, fluoro or hydroxy.

[0089] In one embodiment, R 3can be phenyl, pyridyl or benzodioxolyl, and R 3-1 It may be methoxy, chloro, hydroxy or cyano.

[0090] In one embodiment, L can be -NH-, -NHCH2-, -NH(CH2)2-, -NHC(O)-, -NHSO2-, or -S-.

[0091] In one embodiment, R 4 It can be phenyl, naphthyl, furanyl, pyrazolyl, dihydropyridinyl, pyridinyl, pyrimidinyl, pyridone, pyrimidinone, isoxazolyl, piperidinyl, benzodioxolyl, isoindolinone, dihydroisoquinolinone, benzofuranyl, benzothiophenyl, indolyl, indazolyl, quinolinyl, quinolinone, isoquinolinone, dihydropyrrolopyridone, benzoisoxazolone, dihydronaphthyridinone, benzoxazolyl, benzisoxazolyl, triazolopyridone, phthalazinone, quinazolinone or pyridopyrimidone.

[0092] In one embodiment, Q can be methyl, propyl, isopropyl, fluoro, chloro, bromo, hydroxy, trifluoromethyl, methoxy, nitro, cyano, amino, carboxylate, carboxyl, CHR 5 、CH2R 5 NR 5 R 6 、C(O)R 5 、C(O)OR 5 、C(O)NR 5 R 6 、NHC(O)R 5 、NHC(O)CH2R 5 、NHC(O)(CH2)2R 5 、NHC(O)CH2OR 5 、NHC(O)CH2NR 5 R 6 、NHCH2CH2R 5 NR 5 C(O)R 6 , tetrazolyl, oxadiazolyl, oxadiazolone, furanyl, thienyl, imidazolyl, pyrazolyl, isoxazolyl, thiazolyl, oxy-thiadiazolyl, thio-oxadiazolyl, pyridyl, pyrimidinyl, azetidinyl, oxazolidinone, piperidinyl, piperazinyl, morpholinyl, azaspiroheptane, azaspirooctane, azaspirononane, azabicycloheptane, or azabicyclooctanyl, R5 can be H, methyl, ethyl, butyl, cyclopropyl, cyclohexane, methoxy, amino, phenyl, benzyl, imidazolyl, oxadiazolyl, oxadiazolone, pyridyl, pyrimidinyl, azetidinyl, piperidinyl, piperidone, piperazinyl, morpholinyl, thiazolidinedione, piperazinone, piperazine-dione, azaspiroheptane, or azaspirononane, and R 6 It can be H, methyl, ethyl, propyl, isopropyl, sulfonyl, pyrazolyl, pyridinyl, pyridazinyl, azetidinyl or piperidinyl.

[0093] In one embodiment, R 7 It may be methyl, propyl, isopropyl, cyclopropyl, fluorine, chlorine, difluoromethyl, trifluoromethyl, hydroxy, methoxy, hydroxymethyl, cyano, amino, dimethylamino, methylcarboxylate, tert-butylcarboxylate, nitro, isoxazolyl, thiazolyl, pyridyl or oxadiazolylmethyl.

[0094] Unless otherwise defined, the following definitions are used in this specification when defining compounds of Formula 1.

[0095] The term "alkyl" refers to a straight or branched hydrocarbon group, preferably C1-C 10 Alkyl. Examples of alkyl groups include, but are 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.

[0096] The term "cycloalkyl" refers to a partially saturated or fully saturated monocyclic hydrocarbon or condensed ring hydrocarbon, preferably C3-C 10 Examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and cyclohexenyl.

[0097] The term "hydroxy" or "hydroxyl" is defined as -OH, and the term "alkoxy" refers to an alkyloxy group in which the hydrogen atom of the hydroxy group is replaced by 1 to 10 alkyl groups, unless otherwise defined.

[0098] The term "halogen" or "halo" refers to Fluorine / Fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).

[0099] The terms "haloalkyl" and "haloalkoxy" refer to an alkyl or alkoxy group substituted with one or more than one halogen atom.

[0100] The term "heteroatom" refers to N, O or S.

[0101] The term "aryl" refers to aromatic hydrocarbons, including polycyclic aromatic ring systems in which a carbocyclic aromatic ring or heteroaryl ring is fused to one or more other rings. 5-12 Aryl, more preferably C 5-10 Aryl. For example, aryl includes, but is not limited to, phenyl, naphthyl, tetrahydronaphthyl, and the like. Also included are groups in which a heteroaryl ring is fused to a cycloalkyl or non-aromatic heterocycle, such as indanyl or tetrahydrobenzopyranyl.

[0102] The term "heteroaryl" or "aromatic heterocycle" refers to a heterocyclic ring having one or more heteroatoms selected from N, O and S as ring atoms and forming a heterocyclic ring that can be combined with benzo or C 3-8 A 3- to 12-membered, more preferably a 5- to 10-membered, aromatic hydrocarbon group fused to a cycloalkyl monocyclic or condensed ring. For example, heteroaryl includes, but is not limited to, pyrrolyl, imidazolyl, pyrazolyl, triazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl, oxadiazolyl, isoxadiazolyl, tetrazolyl, indolyl, indazolyl, isoxazolyl, oxazolyl, thiazolyl, isothiazolyl, furyl, benzofuranyl, thienyl, benzothiazolyl, benzoxazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, and the like.

[0103] Representative examples of the heterocyclic compounds according to the present invention are as follows:

[0104] [1]7-phenylpyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0105] [2] (7-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0106] [3] methyl 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate,

[0107] [4] (7-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

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

[0109] [6] 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile,

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

[0111] [8] (7-(2-chloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0112] [9] (7-(5-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone,

[0113]

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

[0114]

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

[0115]

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

[0116]

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

[0117]

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

[0118]

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

[0119]

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

[0120]

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

[0121]

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

[0122]

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

[0123]

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

[0124]

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

[0125]

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

[0126]

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

[0127]

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

[0128]

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

[0129]

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

[0130]

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

[0131]

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

[0132]

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

[0133]

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

[0134]

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

[0135]

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

[0136]

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

[0137]

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

[0138]

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

[0139]

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

[0140]

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

[0141]

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

[0142]

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

[0143]

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

[0144]

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

[0145]

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

[0146]

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

[0147]

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

[0148]

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

[0149]

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

[0150]

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

[0151]

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

[0152]

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

[0153]

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

[0154]

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

[0155]

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

[0156]

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

[0157]

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

[0158]

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

[0159]

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

[0160]

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

[0161]

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

[0162]

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

[0163]

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

[0164]

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

[0165]

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

[0166]

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

[0167]

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

[0168]

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

[0169]

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

[0170]

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

[0171]

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

[0172]

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

[0173]

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

[0174]

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

[0175]

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

[0176]

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

[0177]

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

[0178]

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

[0179]

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

[0180]

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

[0181]

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

[0182]

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

[0183]

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

[0184]

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

[0185]

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

[0186]

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

[0187]

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

[0188]

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

[0189]

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

[0190]

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

[0191]

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

[0192]

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

[0193]

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

[0194]

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

[0195]

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

[0196]

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

[0197]

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

[0198]

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

[0199]

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

[0200]

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

[0201]

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

[0202]

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

[0203]

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

[0204]

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

[0205]

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

[0206]

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

[0207]

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

[0208]

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

[0209]

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

[0210]

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

[0211]

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

[0212]

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

[0213]

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

[0214]

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

[0215]

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

[0216]

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

[0217]

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

[0218]

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

[0219]

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

[0220]

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

[0221]

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

[0222]

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

[0223]

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

[0224]

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

[0225]

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

[0226]

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

[0227]

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

[0228]

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

[0229]

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

[0230]

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

[0231]

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

[0232]

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

[0233]

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

[0234]

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

[0235]

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

[0236]

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

[0237]

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

[0238]

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

[0239]

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

[0240]

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

[0241]

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

[0242]

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

[0243]

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

[0244]

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

[0245]

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

[0246]

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

[0247]

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

[0248]

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

[0249]

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

[0250]

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

[0251]

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

[0252]

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

[0253]

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

[0254]

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

[0255]

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

[0256]

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

[0257]

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

[0258]

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

[0259]

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

[0260]

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

[0261]

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

[0262]

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

[0263]

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

[0264]

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

[0265]

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

[0266]

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

[0267]

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

[0268]

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

[0269]

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

[0270]

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

[0271]

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

[0272]

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

[0273]

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

[0274]

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

[0275]

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

[0276]

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

[0277]

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

[0278]

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

[0279]

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

[0280]

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

[0281]

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

[0282]

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

[0283]

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

[0284]

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

[0285]

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

[0286]

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

[0287]

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

[0288]

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

[0289]

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

[0290]

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

[0291]

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

[0292]

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

[0293]

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

[0294]

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

[0295]

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

[0296]

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

[0297]

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

[0298]

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

[0299]

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

[0300]

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

[0301]

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

[0302]

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

[0303]

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

[0304]

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

[0305]

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

[0306]

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

[0307]

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

[0308]

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

[0309]

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

[0310]

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

[0311]

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

[0312]

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

[0313]

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

[0314]

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

[0315]

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

[0316]

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

[0317]

[214] 2-azaspiro[3.3]heptan-2-yl-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]methanone,

[0318]

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

[0319]

[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,

[0320]

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

[0321]

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

[0322]

[219] 1-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)azetidine-3-carboxylic acid methyl ester,

[0323]

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

[0324]

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

[0325]

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

[0326]

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

[0327]

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

[0328]

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

[0329]

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

[0330]

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

[0331]

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

[0332]

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

[0333]

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

[0334]

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

[0335]

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

[0336]

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

[0337]

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

[0338]

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

[0339]

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

[0340]

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

[0341]

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

[0342]

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

[0343]

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

[0344]

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

[0345]

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

[0346]

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

[0347]

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

[0348]

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

[0349]

[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,

[0350]

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

[0351]

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

[0352]

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

[0353]

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

[0354]

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

[0355]

[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,

[0356]

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

[0357]

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

[0358]

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

[0359]

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

[0360]

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

[0361]

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

[0362]

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

[0363]

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

[0364]

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

[0365]

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

[0366]

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

[0367]

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

[0368]

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

[0369]

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

[0370]

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

[0371]

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

[0372]

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

[0373]

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

[0374]

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

[0375]

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

[0376]

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

[0377]

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

[0378]

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

[0379]

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

[0380]

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

[0381]

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

[0382]

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

[0383]

[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,

[0384]

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

[0385]

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

[0386]

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

[0387]

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

[0388]

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

[0389]

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

[0390]

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

[0391]

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

[0392]

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

[0393]

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

[0394]

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

[0395]

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

[0396]

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

[0397]

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

[0398]

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

[0399]

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

[0400]

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

[0401]

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

[0402]

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

[0403]

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

[0404]

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

[0405]

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

[0406]

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

[0407]

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

[0408]

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

[0409]

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

[0410]

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

[0411]

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

[0412]

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

[0413]

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

[0414]

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

[0415]

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

[0416]

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

[0417]

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

[0418]

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

[0419]

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

[0420]

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

[0421]

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

[0422]

[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,

[0423]

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

[0424]

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

[0425]

[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,

[0426]

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

[0427]

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

[0428]

[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,

[0429]

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

[0430]

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

[0431]

[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,

[0432]

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

[0433]

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

[0434]

[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,

[0435]

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

[0436]

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

[0437]

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

[0438]

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

[0439]

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

[0440]

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

[0441]

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

[0442]

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

[0443]

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

[0444]

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

[0445]

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

[0446]

[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,

[0447]

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

[0448]

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

[0449]

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

[0450]

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

[0451]

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

[0452]

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

[0453]

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

[0454]

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

[0455]

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

[0456]

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

[0457]

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

[0458]

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

[0459]

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

[0460]

[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,

[0461]

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

[0462]

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

[0463]

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

[0464]

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

[0465]

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

[0466]

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

[0467]

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

[0468]

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

[0469]

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

[0470]

[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,

[0471]

[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,

[0472]

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

[0473]

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

[0474]

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

[0475]

[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,

[0476]

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

[0477]

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

[0478]

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

[0479]

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

[0480]

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

[0481]

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

[0482]

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

[0483]

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

[0484]

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

[0485]

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

[0486]

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

[0487]

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

[0488]

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

[0489]

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

[0490]

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

[0491]

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

[0492]

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

[0493]

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

[0494]

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

[0495]

[392] 6-(3-(7-azaspiro[3.5]nonane-7-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one,

[0496]

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

[0497]

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

[0498]

[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,

[0499]

[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,

[0500]

[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,

[0501]

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

[0502]

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

[0503]

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

[0504]

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

[0505]

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

[0506]

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

[0507]

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

[0508]

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

[0509]

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

[0510]

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

[0511]

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

[0512]

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

[0513]

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

[0514]

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

[0515]

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

[0516]

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

[0517] The compound represented by the above formula 1 according to the present invention can be prepared and used in the form of prodrugs, hydrates, solvates and pharmaceutically acceptable salts to enhance in vivo absorption or increase solubility, and thus prodrugs, hydrates, solvates and pharmaceutically acceptable salts are also within the scope of the present invention.

[0518] 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, while the parent drug may not be. The solubility of the prodrug in a pharmaceutical composition may also be improved compared to the parent drug. For example, a prodrug may be an in vivo hydrolyzable ester of a compound according to the invention and a pharmaceutically acceptable salt thereof. Another example of a prodrug may be a short peptide (polyamino acid) linked to an acidic group that is metabolized to reveal the active site of the peptide.

[0519] The term "hydrate" refers to 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.

[0520] 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. Thus, preferred solvents include those that are volatile, non-toxic and / or suitable for administration to humans.

[0521] The term "isomer" refers to a compound of the present invention or a salt thereof having the same chemical formula or molecular formula but different structures or spaces. Such isomers include structural isomers such as tautomers, stereoisomers such as R isomers or S isomers with an asymmetric carbon center, and geometric isomers (trans, cis). All of these isomers and mixtures thereof are also included within the scope of the present invention.

[0522] The term "pharmaceutically acceptable salt" refers to a salt form of a compound that does not cause severe irritation to an organism to which the compound is administered and does not impair the biological activity and physical properties of the compound. Pharmaceutically acceptable salts include acid addition salts formed with acids that form non-toxic acid addition salts containing pharmaceutically acceptable anions, such as 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 methylsulfonic acid, ethylsulfonic acid, benzenesulfonic acid, p-toluenesulfonic acid, etc. For example, pharmaceutically acceptable carboxylic acid salts include metal salts or alkaline earth metal salts formed with lithium, sodium, potassium, calcium, magnesium, etc.; amino acid salts such as lysine salts, arginine salts, guanidine salts, etc.; organic salts such as dicyclohexylamine, N-methyl-D-glucamine, tris(hydroxymethyl)methylamine, diethanolamine, choline, and triethylamine. The compound of formula 1 according to the present invention can be converted into a salt thereof by a conventional method.

[0523] The present invention also provides a method for preparing the compound of formula 1.

[0524] The method for preparing the compound of Formula 1 of the present invention is illustrated by Scheme 1 to Scheme 55, and the method for preparing the compound of Formula 1 of the present invention is not intended to limit the method for preparing the compound of Formula 1 of the present invention. The methods for preparing the compounds of Reaction Scheme 1 to Reaction Scheme 55 are merely examples, and it is obvious that they can be easily modified by those skilled in the art according to the specific substituents.

[0525] The present invention also provides a pharmaceutical composition for preventing or treating 15-PGDH-related diseases, comprising as an active ingredient a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

[0526] The present invention also provides a method for preventing or treating 15-PGDH-related diseases, comprising administering to a subject in need thereof a therapeutically effective amount of a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

[0527] The present invention also provides the use of a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof as an active ingredient in the preparation of a drug for preventing or treating 15-PGDH-related diseases.

[0528] In one embodiment, the 15-PGDH-related disease can be one or more selected from the following: inflammatory diseases (inflammatory bowel disease (ulcerative colitis, Crohn's disease), chronic obstructive pulmonary disease (COPD), Behcet's disease, acute liver injury, acute kidney injury, acute lung injury, sepsis, exacerbation of asthma and lung disease, peptic ulcer (ulcer caused by NSAID), vasculitis syndrome, non-alcoholic fatty liver disease (NASH), atopic dermatitis, psoriasis, interstitial cystitis, prostatitis syndrome), fibrosis (pulmonary fibrosis (idiopathic pulmonary fibrosis), renal fibrosis (glomerulosclerosis), cardiac fibrosis ( Myocardial fibrosis), oral fibrosis, deltoid fibrosis, hepatic fibrosis, myelofibrosis, scleroderma), autoimmune diseases (systemic lupus erythematosus, rheumatoid arthritis, autoimmune hepatitis, severe combined immunodeficiency syndrome (SCID)), ophthalmological diseases (dry eyes, conjunctivitis, keratitis), thrombocytopenia (drug-induced thrombocytopenia, autoimmune thrombocytopenia, idiopathic thrombocytopenia, thrombocytopenia caused by viral infection); myopathy (muscular dystrophy, muscle damage), anemia (plastic anemia, anemia of chronic disease, Fanconi anemia, β-thalassemia, or anemia of unknown cause), circulatory diseases (heart disease) (angina, heart failure, myocardial infarction), kidney disease (chronic kidney disease, renal failure), stroke, pulmonary hypertension, peripheral circulatory disorders), neuronal cell death (mental disorders, neurodegenerative diseases, nerve damage), cytopenias (immune cytopenias, neutropenia, lymphopenia), osteoporosis, bone fractures, leukemias (acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myeloid leukemia (CML)), lymphomas (Hodgkin lymphoma, non-Hodgkin lymphoma), radiation exposure toxicity, cancers expressing 15-PGDH, multiple myeloma, paroxysmal sleep apnea Proteinuria (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 (vertigo, 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.

[0529] As a result of measuring the 15-PGDH inhibitory activity of the heterocyclic compound of the present invention, it was confirmed that it exhibited excellent 15-PGDH inhibitory activity.

[0530] The present invention also provides a pharmaceutical composition comprising a heterocyclic compound represented by Formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive.

[0531] The above-mentioned additives may include pharmaceutically acceptable carriers or diluents, and can be formulated into oral preparations such as powders, granules, tablets, capsules, suspensions, emulsions, syrups, aerosols; external preparations; suppositories; and sterile injectable solutions according to conventional methods.

[0532] Pharmaceutically acceptable carriers include lactose, dextrose, sucrose, sorbitol, mannitol, xylitol, erythritol, maltitol, starch, gum arabic, alginate, gelatin, calcium phosphate, calcium silicate, cellulose, methylcellulose, microcrystalline cellulose, polyvinylpyrrolidone, water, methylhydroxybenzoate, propylhydroxybenzoate, talc, magnesium stearate, mineral oil, etc. In addition, diluents or excipients such as fillers, bulking agents, adhesives, wetting agents, disintegrants, and surfactants are also included. Oral solid preparations include tablets, pills, powders, granules, capsules, etc., and these solid preparations can contain at least one excipient, such as starch, calcium carbonate, sucrose or lactose, gelatin, etc., and can include lubricants, such as magnesium stearate, talc, etc. Oral liquid preparations include suspensions, oral solutions, emulsions, syrups, and diluents, such as water or liquid paraffin, wetting agents, sweeteners, flavorings, preservatives, etc. Non-digestive tract preparations include sterile aqueous solutions, non-aqueous solvents, suspensions, emulsions, creams, freeze-dried preparations, 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. Operable suppository bases include synthetic fatty acid esters (witepsol), polyethylene glycol, Tween 61, theobroma oil, trilaurin oil (laurin butter) and glycerin gelatin.

[0533] The dosage of the active ingredient contained in the pharmaceutical composition of the present invention varies according to the patient's condition and weight, the extent of the disease, the form of the active ingredient, the route of administration, and the cycle, and can be appropriately adjusted according to the patient. For example, the active ingredient can be administered at a dosage of 0.0001 mg / kg to 1000 mg / kg, preferably 0.001 mg / kg to 100 mg / kg per day, and the dosage can be administered once a day or in divided doses. In addition, the pharmaceutical composition of the present invention can contain an active ingredient in an amount of 0.001% to 90% by weight based on the total weight of the composition.

[0534] The pharmaceutical composition of the present invention can be administered to mammals such as rats, mice, livestock and humans via various routes, for example, orally, transdermally, intraperitoneally, rectally, or by intravenous, intramuscular, subcutaneous, intrauterine or intracerebroventricular injection.

[0535] Hereinafter, the present invention will be described in more detail through Examples and Experimental Examples. However, the following Examples and Experimental Examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

[0536] Example 1: 7-phenylpyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0537] <Scheme 1>

[0538]

[0539] Step 1-1: Pyrazolo[1,5-a]pyridine-3-carboxylic acid (1.0 g, 6.18 mmol) was dissolved in tetrahydrofuran (20 mL) and the temperature was lowered to -20 ° C. Lithium bis(trimethylsilyl)amide dissolved in 1 M tetrahydrofuran (18.5 mL, 18.5 mmol) was slowly added, and the mixture was stirred for 30 minutes. Iodine (1.878 g, 7.4 mmol) dissolved in tetrahydrofuran (5 mL) was added to the reaction solution, and the mixture was stirred for 30 minutes, then the temperature was slowly raised to room temperature, and the mixture was stirred for 12 hours. After the reaction was completed, saturated sodium bicarbonate aqueous solution (50 mL) was added and extracted with dichloromethane (50 mL×3). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. After solidification with a small amount of dichloromethane, filtration and air drying, the target compound 1-1 (1.86 g, 94%) was obtained.

[0540] Step 1-2: Compound 1-1 (1.7 g, 5.9 mmol) was dissolved in N,N-dimethylformamide (30 mL), HATU (2.69 g, 7.1 mmol) and DIPEA (3.1 mL, 17.7 mmol) were added, and the mixture was stirred at room temperature for 10 minutes. Piperidine (0.7 mL, 7.1 mmol) was added to the reaction solution, and the mixture was stirred for 4 hours. After the reaction was completed, the reaction solution was concentrated, diluted with ethyl acetate (100 mL), and washed with water (50 mL), saturated aqueous ammonium chloride solution (50 mL), saturated aqueous sodium bicarbonate solution (50 mL) and brine (50 mL) in sequence. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated. After solidification with ether / ethyl acetate (10:1) solution (20 mL), it was 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, azabenzotriazole tetramethyluronium hexafluorophosphate), DIPEA (N,N-diisopropylethylamine)].

[0541] Step 1-3: Compound 1-2 (70 mg, 0.19 mmol) was dissolved in 1,4-dioxane (7 mL), phenylboric acid (24 mg, 0.19 mmol), tetrakis(triphenylphosphine)palladium (57 mg, 0.04 mmol) and 2M potassium carbonate aqueous solution (0.19 mL, 0.39 mmol), nitrogen was introduced for 10 minutes, and the mixture was stirred at 100 ° C for 12 hours. After the reaction was completed, the reaction solution was concentrated and diluted with dichloromethane (10 mL). The remaining palladium was filtered out using Celite, and the filtrate was washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated using column chromatography to obtain the target compound 1 (42.3 mg, 70%).

[0542] 1 H 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).

[0543] MS (ESI, LR) calculated value C 19 H 20 N3O[M+H] + :306.2, measured value:306.2

[0544] Example 2. (7-(3-chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0545] Example 3. Methyl 3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate

[0546] Example 4. (7-(3-methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0547] Example 5. (7-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0548] Example 6. 3-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0549] Example 8. (7-(2-chloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0550] Example 10. 4-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoic acid

[0551] Example 11. Methyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoate

[0552] Example 12. (7-(4-Chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0553] Example 13. (7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0554] Example 15. 4-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0555] Example 16. (7-(6-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0556] Example 18. 5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)cyanopyridine

[0557] Example 19. (7-(6-Fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0558] Example 20. (7-(4-methoxy-3-(trifluoromethyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0559] Example 21. (7-(3-chloro-4-hydroxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone]

[0560] Example 22. 2-Fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0561] Example 23. 2-(Dimethylamino)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0562] Example 24. (7-(3,4-Dimethoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0563] Example 25. (7-(1-Methyl-1H-pyrazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0564] Example 120. tert-Butyl 4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,6-dihydropyridine-1(2H)-carboxylate

[0565] Example 121. (7-(Benzo[d][1,3]dioxol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0566] Example 122. (7-(Benzofuran-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0567] Example 123. (7-(Benzofuran-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0568] Example 124. (7-(Benzo[b]thiophen-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0569] Example 125. (7-(1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0570] Example 126. (7-(1H-Indol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0571] Example 127. (7-(Benzofuran-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0572] Example 128. (7-(Naphth-1-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0573] Example 129. (7-(Naphthyl-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0574] Example 130. Piperidin-1-yl(7-(quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[0575] Example 131. 7-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[0576] Example 134. 7-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one

[0577] Example 136. 6-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[0578] Example 138. 6-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one

[0579] Example 140. 6-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[0580] Example 143. 5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[0581] Example 145. 6-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinolin-2(1H)-one

[0582] Example 195. 3-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one

[0583] Example 205. 3-Fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carbonitrile

[0584] Example 207. 3-Methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-4(3H)-one

[0585] Example 224. 7-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1(2H)-one

[0586] 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

[0587] Example 233. 6-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phthalazin-1(2H)-one

[0588] Example 244. Methyl 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylate

[0589] Example 245. 3-Methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one

[0590] 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

[0591] Example 251. 3-Methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)quinazolin-4(3H)-one

[0592] 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

[0593] Example 254. 2-Fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile

[0594] Example 255. 3-Methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[2,3-d]pyrimidin-4(3H)-one

[0595] Example 256. 3-Methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrido[3,2-d]pyrimidin-4(3H)-one

[0596] Example 264. (7-(2-Chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0597] Example 265. (7-(5-Bromo-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0598] Example 266. (7-(2,6-Difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0599] Example 267. (7-(2-Chloropyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0600] Example 268. 2-Methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzo[d]isoxazol-3(2H)-one

[0601] Example 269. (7-(3-Methoxybenzo[d]isoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0602] Example 270. 2-(Dimethylamino)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridine cyanide

[0603] Example 271. (7-(6-Fluoropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0604] Example 272. (7-(2-Chloro-6-(trifluoromethyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0605] Example 273. (7-(2,6-Difluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0606] Example 279. (7-(3-Chloro-5-fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0607] 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

[0608] Example 281. (7-(6-Chloro-5-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0609] Example 282. (7-(2,6-Dichloropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0610] Example 283. (7-(5-chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0611] Example 284. (7-(5-Fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0612] Example 285. 3-Fluoro-4-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzonitrile

[0613] Example 288. (7-(5,6-Difluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0614] Example 289. (7-(5-chloro-6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0615] Example 290. 2,6-Difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0616] Example 291. 3-Fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0617] Example 292. (7-(4-Bromophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0618] Example 293. 5-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrimidine-2-carbonitrile

[0619] Example 294. [7-(2-Hydroxypyrimidin-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[0620] Example 298. (7-(5-chloro-2-fluoropyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0621] Example 312. 3-Nitro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[0622] Example 313. (7-(6-Bromopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0623] Example 314. (7-(6-chloropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0624] Example 315. (7-(6-Chloro-2-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0625] Example 318. (7-(5-nitropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0626] For Example 2, Example 3, Example 4, Example 5, Example 6, Example 8, Example 10, Example 11, Example 12, Example 13, Example 15, Example 16, Example 18, Example 19, Example 20, Example 21, Example 22, Example 23, Example 24, Example 25, Example 120, Example 121, Example 122, Example 123, Example 124, Example 125, Example 126, Example 127, Example 128, Example 129, Example 130, Example 131, Example 134, Example 136, Example 138, Example 140, Example 143, Example 145, Example 195, Example 205, Example 207, Example 224, Example 232, Example 233, Example 244, Example 245 5. Example 246, Example 251, Example 252, Example 254, Example 255, Example 256, Example 264, Example 265, Example 266, Example 267, Example 268, Example 269, Example 270, Example 271, Example 272, Example 273, Example 279, Example 280, Example 281, Example 282, Example 283, Example 284, Example 285, Example 288, Example 289, Example 290, Example 291, Example 292, Example 293, Example 294, Example 298, Example 312, Example 313, Example 314, Example 315, and Example 318 were obtained using the corresponding compound and compound 1-2 by the same synthesis method as steps 1-3 in Example 1. The structural data and spectral data are shown in Table 1 below.

[0627] [Table 1]

[0628]

[0629]

[0630]

[0631]

[0632]

[0633]

[0634]

[0635]

[0636]

[0637]

[0638]

[0639]

[0640]

[0641]

[0642]

[0643]

[0644] Example 7. (7-(3-aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0645] <Scheme 2>

[0646]

[0647] 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. Hydrogen was introduced into the reaction solution and stirred for 12 hours. After the reaction was completed, Celite was used to remove the remaining palladium 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 separated by column chromatography to obtain the target compound 7 (0.297 g, 95%).

[0648] 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).

[0649] MS (ESI, LR) calculated value C 19 H 21 N4O[M+H] + :321.2, measured value:321.2.

[0650] Example 9. (7-(5-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0651] Example 14. (7-(4-Aminophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0652] Example 17. (7-(6-aminopyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0653] For Examples 9, 14, and 17, the corresponding compounds and Compound 1-2 were used to obtain the compounds by sequentially following the synthesis methods of Steps 1-3 in Example 1 and the synthesis method of Example 7. The structural and spectral data are shown in Table 2 below.

[0654] [Table 22]

[0655]

[0656] Example 26. (7-(3-(Morpholine-4-carbonyl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0657] <Scheme 3>

[0658]

[0659] Step 26-1: Compound 1-2 and 3-carboxyphenylboronic acid were used to obtain the target compound 26-1 by the same synthesis method as Step 1-3 in Example 1.

[0660] Step 26-2: Compound 26-1 and morpholine were used to obtain the target compound 26 by the same synthesis method as Step 1-2 of Example 1.

[0661] 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).

[0662] MS (ESI, LR) calculated value C 24 H 27 N4O3[M+H] + :419.2, measured value:419.2.

[0663] Example 27. N-methyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0664] Example 28. N-isopropyl-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide,

[0665] Example 29. Azetidin-1-yl(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0666] Example 30. N-(2-methoxyethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0667] Example 31. N-(2-(Dimethylamino)ethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0668] Example 32. N-(Cyclopropylmethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0669] Example 33. N-(1-methylpiperidin-4-yl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0670] Example 35. tert-Butyl 4-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzoyl)piperazine-1-carboxylate

[0671] Example 36. N-(2-cyanoethyl)-3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0672] Example 37. 3-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide

[0673] Example 38. 3-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide

[0674] For Examples 27, 28, 29, 30, 31, 32, 33, 35, 36, 37, and 38, the corresponding compounds and compound 26-1 were used to obtain the compounds by the same synthesis method as in Steps 1-2 of Example 1. The structural and spectral data are shown in Table 3 below.

[0675] [Table 3]

[0676]

[0677]

[0678]

[0679] Example 34. Piperazin-1-yl(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0680] <Scheme 4>

[0681]

[0682] Compound 35 (0.1 g, 0.19 mmol) was dissolved in dichloromethane (1 mL) and stirred at 0°C for 10 minutes. 1,4-Dioxane dissolved in 4N hydrochloric acid (0.48 mL) was added, and the mixture was stirred at room temperature for 16 hours. After the reaction was complete, the reaction solution was concentrated and separated using column chromatography to obtain the target compound 34 (36 mg, 44%).

[0683] 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), 7.5 4(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).

[0684] MS (ESI, LR) calculated value C 24 H 28 N5O2[M+H] + :418.2, measured value:418.2.

[0685] Example 39. (7-(5-(Morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0686] <Scheme 5>

[0687]

[0688] Step 39-1: Using compound 1-2 and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-3-carboxylic acid methyl ester, the target compound 39-1 was obtained by the same synthesis method as step 1-3 in Example 1.

[0689] Step 39-2: Compound 39-1 and morpholine were used to obtain the target compound 39 by the same synthesis method as in Step 1-2 of Example 1.

[0690] 1 H 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=7.1,1.4Hz,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).

[0691] MS (ESI, LR) calculated value C 23 H 26 N5O3[M+H] + :420.2, measured value:420.2.

[0692] Example 40. N-Methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0693] Example 41. Azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0694] Example 42. (3-Hydroxyazetidin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0695] 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

[0696] Example 44. (3,3-Difluoroazetidin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0697] Example 45. N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0698] Example 46. N-(Cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0699] Example 47. N-(1-methylpiperidin-4-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0700] Example 51. N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0701] Example 52. N-(Cyanomethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0702] Example 53. 5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)nicotinamide

[0703] Example 54. 5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)nicotinamide

[0704] Example 55. N-(Isoxazolyl-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0705] Example 56. 5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridazin-4-yl)nicotinamide

[0706] Example 57. 5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(thiazol-5-ylmethyl)nicotinamide

[0707] Example 192. (3-Fluoroazetidin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0708] Example 193. N-(1-methyl-1H-pyrazol-3-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0709] Example 201. N-Methylsulfonyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide

[0710] Example 203. 4-[5-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazin-2-one

[0711] Example 204. 4-[5-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carbonyl]piperazine-2,6-dione

[0712] Example 225. (6-Hydroxy-2-azaspiro[3.3]heptane-2-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone

[0713] Example 226. 2-Oxa-7-azaspiro[3.5]nonan-7-yl-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridinyl]methanone,

[0714] For Examples 40, 41, 42, 43, 44, 45, 46, 47, 51, 52, 53, 54, 55, 56, 57, 192, 193, 201, 203, 204, 225, and 226, the corresponding compounds and compound 39-1 were used to obtain the compounds by the same synthesis method as in Steps 1-2 of Example 1. The structural and spectral data are shown in Table 4 below.

[0715] [Table 4]

[0716]

[0717]

[0718]

[0719]

[0720]

[0721]

[0722] Example 48. Piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0723] Example 200. N-(azetidin-3-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)nicotinamide

[0724] The target compound was obtained using the corresponding compound and compound 39-1 by sequentially following the same synthesis methods as steps 1-2 in Example 1 and the synthesis method of Example 34. The structural data and spectral data are shown in Table 5 below.

[0725] [Table 5]

[0726]

[0727] Example 49. (4-Methylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0728] <Scheme 6>

[0729]

[0730] Compound 48 (50 mg, 0.12 mmol) was dissolved in ethanol (0.6 mL) and water (0.6 mL), 37% formaldehyde (17.8 μL, 0.24 mmol) was added, and the mixture was stirred at 60° C. for 1 hour. Sodium cyanoborohydride (15 mg, 0.24 mmol) and acetic acid (6.8 μL, 0.12 mmol) were added to the reaction solution, and the mixture was stirred at 60° C. for 12 hours. The reaction solution was concentrated and separated using column chromatography to obtain the target compound 49 (30 mg, 57%).

[0731] 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).

[0732] MS (ESI, LR) calculated value C 24 H 29 N6O2[M+H] + :433.2, measured value:433.1.

[0733] Example 202. N-(1-methylazetidin-3-yl)-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide

[0734]

[0735] Using compound 200 and the corresponding compound, the target compound 202 was obtained using the same synthesis method as Example 49.

[0736] 1H 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).

[0737] MS (ESI, LR) calculated value C 23 H 27 N6O2[M+H] + :419.1, measured value:419.1.

[0738] Example 50. (4-Isopropylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)methanone

[0739]

[0740] The target compound 50 was obtained by the synthesis method used in Example 49 using compound 48 and acetone.

[0741] 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).

[0742] MS (ESI, LR) calculated value C 26 H 33 N6O2[M+H] +:461.3, measured value:461.2.

[0743] Example 58. N-Methyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0744] Example 59. N,N-Dimethyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0745] Example 60. N-Isopropyl-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0746] Example 61. Azetidin-1-yl(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0747] Example 62. N-(2-methoxyethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0748] Example 63. N-(2-(Dimethylamino)ethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0749] Example 64. N-(Cyclopropylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0750] Example 65. N-(1-methylpiperidin-4-yl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0751] Example 69. N-(2-cyanoethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0752] Example 70. N-(Cyanomethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0753] Example 71. 4-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)benzamide

[0754] Example 72. 4-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)benzamide

[0755] Example 73. N-(Isoxazol-3-ylmethyl)-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzamide

[0756] For Examples 58, 59, 60, 61, 62, 63, 64, 65, 69, 70, 71, 72, and 73, the corresponding compounds and Compound 10 were used to obtain the compounds by the same synthesis method as in Steps 1-2 of Example 1. The structural data and spectral data are shown in Table 6 below.

[0757] [Table 6]

[0758]

[0759]

[0760]

[0761]

[0762] Example 66. Piperazin-1-yl(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0763]

[0764] Using compound 10 and 1-Boc-piperazine, the target compound 66 was obtained by sequentially following the synthetic methods of steps 1-2 in Example 1 and the synthetic method of Example 34.

[0765] 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).

[0766] MS (ESI, LR) calculated value C 24 H 28 N5O2[M+H] + :418.2, measured value:418.1.

[0767] Example 67. (4-Methylpiperazin-1-yl)(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0768] Example 68. (4-Isopropylpiperazin-1-yl)(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)methanone

[0769] For Example 67 and Example 68, the corresponding compounds and Compound 66 were used to obtain the compounds by the same synthesis method as Example 49. The structural data and spectral data are shown in Table 7 below.

[0770] [Table 7]

[0771]

[0772] Example 74. (7-(6-(Morpholine-4-carbonyl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0773] <Scheme 7>

[0774]

[0775] The target compound 74 was obtained by the same synthesis method as Example 39 using compound 1-2 and 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-carboxylic acid methyl ester.

[0776] 1 H 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).

[0777] MS (ESI, LR) calculated value C 23 H 26 N5O3[M+H] + :420.2, measured value:420.1.

[0778] Example 75. N-Methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0779] Example 76. N-Isopropyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0780] Example 77. Azetidin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0781] Example 78. N-(2-methoxyethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0782] Example 79. N-(2-(Dimethylamino)ethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0783] Example 80. N-(Cyclopropylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0784] Example 81. N-(1-methylpiperidin-4-yl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0785] Example 85. N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0786] Example 86. N-(Cyanomethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0787] Example 87. 5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-3-yl)picolinamide

[0788] Example 88. 5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-N-(pyridin-4-yl)picolinamide

[0789] Example 89. N-(Isoxazolyl-3-ylmethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)picolinamide

[0790] Example 213. (3-Fluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone

[0791] Example 214. 2-Azaspiro[3.3]heptan-2-yl-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]methanone

[0792] Example 237. (3,3-Difluoroazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridyl]methanone

[0793] For Examples 75, 76, 77, 78, 79, 80, 81, 85, 86, 87, 88, 89, 213, 214, and 237, the corresponding compounds and Compound 74-1 were used to obtain the compounds by the same synthesis method as in Steps 1-2 of Example 1. The structural and spectral data are shown in Table 8 below.

[0794] [Table 8]

[0795]

[0796]

[0797]

[0798]

[0799] Example 82. Piperazin-1-yl(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0800]

[0801] Using compound 74-1 and 1-Boc-piperazine, the target compound 82 was obtained by sequentially following the synthetic methods of steps 1-2 in Example 1 and the synthetic method of Example 34.

[0802] 1H 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).

[0803] MS (ESI, LR) calculated value C 23 H 27 N6O2[M+H] + :419.2, measured value:419.1.

[0804] Example 83. (4-Methylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0805] Example 84. (4-Isopropylpiperazin-1-yl)(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanone

[0806] For Examples 83 and 84, the corresponding compounds and compound 74-1 were used to obtain the compounds by the same synthesis method as in Example 49. The structural data and spectral data are shown in Table 9 below.

[0807] [Table 9]

[0808]

[0809]

[0810] Example 243. 3-Fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid

[0811] <Scheme 8>

[0812]

[0813] Step 243-1: Using compound 1-2 and (5-fluoro-6-(methoxycarbonyl)pyridin-3-yl)boronic acid, the target compound 243-1 was obtained by the same synthesis method as step 1-3 in Example 1.

[0814] Step 243-2: Compound 243-1 (19 mg, 49 μM) was dissolved in tetrahydrofuran (1 mL), 1N sodium hydroxide (0.3 mL) was added, and the mixture was stirred at 0°C for 2 hours. After the reaction was completed, water (3 mL) was added to the reaction solution and washed with dichloromethane solution. The aqueous layer was acidified with 1N hydrochloric acid, the pH of the aqueous solution was adjusted to 2, and then extracted with dichloromethane (5 mL×3). The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated to obtain the target compound 243 (12 mg, 66%).

[0815] 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).

[0816] MS (ESI, LR) calculated value C 19 H 18 FN4O3[M+H] + :369.1, measured value:369.1.

[0817] Example 248. [7-[6-(azetidine-1-carbonyl)-5-fluoro-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[0818]

[0819] The target compound 248 was obtained by the same synthetic method as in Step 1-2 of Example 1 using Compound 243 and azetidine.

[0820] 1H NMR (400MHz, DMSO-d6) δ (ppm): 9.02 (t, J = 1.5 Hz, 1H), 8.53 (dd, J = 11.2, 1.7 Hz, 1H),8.30(s,1H),7.97(dd,J=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).

[0821] MS (ESI, LR) calculated value C 22 H 23 FN5O2[M+H] + :408.2, measured value:408.1.

[0822] Example 249. [7-[5-Fluoro-6-(morpholine-4-carbonyl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[0823] Example 250. 3-Fluoro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide

[0824] For Example 249 and Example 250, the target compounds were obtained using the corresponding compounds and Compound 243 using the same synthesis method as Steps 1-2 in Example 1. The structural and spectral data are shown in Table 10 below.

[0825] [Table 10]

[0826]

[0827]

[0828] Example 277. [7-[2-(azetidine-1-carbonyl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone,

[0829] <Scheme 9>

[0830]

[0831] Compound 277-1 was obtained using compound 1-2 and (2-(methoxycarbonyl)pyrimidin-5-yl)boronic acid by the same synthesis method as step 1-3 in Example 1, and then the target compound 277 was obtained using azetidine by the same synthesis method as step 1-2 in Example 1.

[0832] 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=7.7Hz,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).

[0833] MS (ESI, LR) calculated value C 21 H 23 N6O2[M+H] + :391.2, measured value:391.1.

[0834] Example 258. 3-Chloro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid

[0835]

[0836] Using (5-chloro-6-(methoxycarbonyl)pyridin-3-yl)boronic acid, the intermediate was obtained by the same synthesis method as in Step 1-3 of Example 1, and then the target compound 258 was obtained by the same synthesis method as in Step 243-2 of Example 243.

[0837] 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).

[0838] MS (ESI, LR) calculated value C 19 H 18 ClN4O3[M+H] + :385.1, measured value:385.1.

[0839] Example 262. 3-Chloro-N-methyl-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxamide

[0840] Example 286. [7-[6-(Azetidine-1-carbonyl)-5-chloro-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[0841] For Example 262 and Example 286, the corresponding compounds and Compound 258 were used to obtain the compounds by the same synthesis method as Steps 1-2 in Example 1. The structural data and spectral data are shown in Table 11 below.

[0842] [Table 11]

[0843]

[0844] MS (ESI, LR) calculated value C 22 H 23 ClN5O2[M+H] + :424.1, measured value:424.1.

[0845] Example 90. N-(2-cyanoethyl)-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)furan-2-carboxamide

[0846] <Scheme 10>

[0847]

[0848] 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 the target compound 90 was obtained by the same synthesis method as step 1-2 in Example 1 using 3-aminopropionitrile.

[0849] 1H 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).

[0850] MS (ESI, LR) calculated value C 21 H 22 N5O3[M+H] + :392.2, measured value:392.1.

[0851] Example 230. (3-Hydroxyiminoazetidin-1-yl)-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-3-pyridyl]methanone

[0852]

[0853] After obtaining an intermediate by the same synthesis method as Step 1-2 of Example 1 using Compound 39-1 and azetidin-3-one, the target compound 230 was obtained by the same synthesis method as Step 236-2 of Example 236.

[0854] 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).

[0855] MS (ESI, LR) calculated value C 22 H 23 N6O3[M+H] + :419.2, measured value:419.1.

[0856] Example 91. 3-Methoxy-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide

[0857] Example 93. 1-Methyl-N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide

[0858] Example 94. N-(3-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropylcarboxamide

[0859] Example 95. N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide

[0860] Example 96. N-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexylcarboxamide

[0861] For Example 91, Example 93, Example 94, Example 95 and Example 96, the corresponding compounds and Compound 7 were used to obtain the compounds by the same synthesis method as Steps 1-2 in Example 1. The structural data and spectral data are shown in Table 12 below.

[0862] [Table 12]

[0863]

[0864]

[0865] Example 92. 1-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)urea

[0866] <Scheme 11>

[0867]

[0868] 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 stirred at 50° C. for 12 hours. After the reaction was completed, the temperature was lowered with ice water and the precipitated solid was filtered. The target compound 92 (35.6 mg, 45%) was obtained by recrystallization from boiling water.

[0869] 1H 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).

[0870] MS (ESI, LR) calculated value C 20 H 22 N5O2[M+H] + :364.2, measured value:364.2.

[0871] Example 97. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)acetamide

[0872] Example 98. 3-Methoxy-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)propanamide

[0873] Example 99. 1-Methyl-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)piperidine-4-carboxamide

[0874] Example 100. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclopropylcarboxamide

[0875] Example 101. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide

[0876] Example 102. N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)cyclohexylcarboxamide

[0877] Example 274. N-(4-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide

[0878] For Examples 97, 98, 99, 100, 101, 102, and 274, the corresponding compounds and Compound 14 were used to obtain the compounds by the same synthesis method as Steps 1-2 in Example 1. The structural data and spectral data are shown in Table 13 below.

[0879] [Table 13]

[0880]

[0881]

[0882] Example 196. 2-(Dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0883] Example 197. 3-Methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acrylamide

[0884] Example 198. 2-Oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)piperidine-4-carboxamide

[0885] Example 326. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide

[0886] Example 327. N-(5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyridin-3-yl)acetamide

[0887] 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

[0888] Example 334. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)pyrimidine-5-carboxamide

[0889] Example 335. 5-Fluoro-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)nicotinamide

[0890] 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

[0891] Example 389. 2-Phenyl-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0892] Example 402. 2-(5-fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0893] Example 403. N-(5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)-2-(pyrimidin-5-yl)acetamide

[0894] Example 406. 2-(4-Chlorophenoxy)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-3-yl)acetamide

[0895] For Examples 196, 197, 198, 326, 327, 333, 334, 335, 388, 389, 402, 403, and 406, the corresponding compounds and compound 9 were used to obtain the compounds by the same synthesis method as in Steps 1-2 of Example 1. The structural data and spectral data are shown in Table 14 below.

[0896] [Table 14]

[0897]

[0898]

[0899]

[0900]

[0901] Example 103. 3-Methoxy-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)propanamide

[0902] <Scheme 12>

[0903]

[0904] Compound 17 (50 mg, 0.16 mmol) was dissolved in N,N-dimethylformamide (5 mL), and triethylamine (64 μL, 0.47 mmol) was added. 3-Methoxypropionyl chloride (28 mg, 0.23 mmol) was added to the reaction solution, and the mixture was stirred at room temperature for 12 hours. After the reaction was completed, 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, concentrated, and then separated by column chromatography to obtain the target compound 103 (27.2 mg, 43%).

[0905] 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=10.7,5.7 Hz, 6H), 3.26 (s, 3H), 2.70 (t, J = 6.2Hz, 2H), 1.65 (d, J = 5.6Hz, 2H), 1.57 (s, 4H).

[0906] MS (ESI, LR) calculated value C 23 H 28 N5O3[M+H] + :408.2, measured value:408.1.

[0907] Example 104. 2-(Dimethylamino)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide

[0908] <Scheme 13>

[0909]

[0910] HOBt (21 mg, 0.16 mmol) and EDCI·HCl (71.6 mg, 0.37 mmol) were dissolved in dichloromethane (10 mL), triethylamine (64.7 μL, 0.47 mmol) was added, and stirred for 1 hour. Compound 17 (0.1 g, 0.31 mmol) was added to the reaction solution and stirred for 3 hours. After 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 separated by column chromatography to obtain the target compound 104 (36.3 mg, 29%). [HOBt (hydroxybenzotriazole), EDCI (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide)]

[0911] 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), 7.5 2(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).

[0912] MS (ESI, LR) calculated value C 22 H 27 N6O2[M+H] + :407.2, measured value:407.1.

[0913] Example 105. 2-Oxo-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)piperidine-4-carboxamide

[0914] <Scheme 14>

[0915]

[0916] HOBt (42 mg, 0.31 mmol), EDCI·HCl (58 mg, 0.37 mmol) and 4-dimethylaminopyridine (19 mg, 0.15 mmol) were dissolved in dichloromethane (7 mL), triethylamine (86 μL, 0.62 mmol) was added, and stirred for 1 hour. Compound 17 (0.1 mg, 0.31 mmol) was added to the reaction solution and 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 by column chromatography to obtain the target compound 105 (29.8 mg, 22%).

[0917] 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).

[0918] MS (ESI, LR) calculated value C 24 H 27 N6O3[M+H] + :447.2, measured value:447.1

[0919] Example 106. N-(5-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)-2-(pyridin-3-yl)acetamide

[0920]

[0921] The target compound 106 was obtained by the same synthesis method as Example 105 using compound 17 and 2-(3-pyridyl)acetic acid.

[0922] 1H 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).

[0923] MS (ESI, LR) calculated value C 25 H 25 N6O2[M+H] + :441.2, measured value:441.1

[0924] Example 407. N-[5-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]-2-pyrimidin-5-yl-acetamide

[0925] Example 408. N-[5-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]-2-[6-(trifluoromethyl)-3-pyridinyl]acetamide

[0926] Example 409. 2-(5-Fluoropyridin-3-yl)-N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)acetamide

[0927] Example 410. 2-(4-Chlorophenoxy)-N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]acetamide

[0928] For Example 407, Example 408, Example 409 and Example 410, Compound 17 and the corresponding compound were used to obtain the compounds by the same synthesis method as Steps 1-2 in Example 1. The structural data and spectral data are shown in Table 15 below.

[0929] [Table 15]

[0930]

[0931] Example 278. N-(2,6-Difluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-2-(pyridin-3-yl)acetamide

[0932] <Scheme 15>

[0933]

[0934] Step 278-1: Using 4-bromo-2,6-difluoroaniline and 2-(3-pyridyl)acetic acid, the target compound 278-1 was obtained by the same synthesis method as Step 1-2 in Example 1.

[0935] Step 278-2: Compound 278-1 was used to obtain the target compound 278-2 by the same synthesis method as Step 351-1 of Example 351.

[0936] Step 278-3: Compound 278-2 was used to obtain the target compound 278 by the same synthesis method as Step 159-3 of Example 159.

[0937] 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).

[0938] MS (ESI, LR) calculated value C 26 H 24 F2N5O2[M+H] + :476.2, measured value:476.1.

[0939] Example 107. (7-(6-((3-methoxypropyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0940] <Scheme 16>

[0941]

[0942] Potassium carbonate (0.106 g, 0.77 mmol) was added to a solution of 3-methoxypropylamine (47 μL, 0.46 mmol) in N,N-dimethylformamide (6 mL) and stirred for 10 minutes. Compound 19 (0.1 g, 0.31 mmol) was added to the reaction solution, and the mixture was stirred at 100 ° C for 12 hours. After the reaction was completed, 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 then separated by column chromatography to obtain the target compound 107 (0.059 g, 49%).

[0943] 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).

[0944] MS (ESI, LR) calculated value C 22 H 28 N5O2[M+H] + :394.2, measured value:394.2.

[0945] Example 108. (7-(6-morpholinylpyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0946] Example 109. (7-(6-(Isopropylamino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0947] Example 110. Piperidin-1-yl(7-(6-(piperidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[0948] Example 111. (7-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0949] Example 206. (7-(6-(azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0950] Example 208. (7-(6-(3-Fluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0951] Example 209. (7-(6-(3,3-Difluoroazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0952] Example 210. (7-(6-(3-Hydroxyazetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0953] Example 215. (7-(6-(2-Azabicyclo[2.2.1]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0954] 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

[0955] 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

[0956] Example 218. (7-(6-(3-(Dimethylamino)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0957] Example 219. Methyl 1-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)azetidine-3-carboxylate

[0958] Example 220. (7-(6-(2-Azaspiro[3.3]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0959] Example 221. (7-(6-(3-(Hydroxymethyl)azetidin-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0960] 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

[0961] 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

[0962] Example 332. Piperidin-1-yl(7-(6-((2-(pyridin-3-yl)ethyl)amino)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[0963] Example 344. (7-(6-(4-amino-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0964] For Example 108, Example 109, Example 110, Example 111, Example 206, Example 208, Example 209, Example 210, Example 215, Example 216, Example 217, Example 218, Example 219, Example 220, Example 221, Example 222, Example 223, Example 332, and Example 344, the compounds were obtained by the same synthesis method used in Example 107 using the corresponding compounds and Compound 19. The structural data and spectral data are shown in Table 16 below.

[0965] [Table 16]

[0966]

[0967]

[0968]

[0969]

[0970]

[0971] Example 287. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide

[0972] <Scheme 17>

[0973]

[0974] Compound 19 (36.5 mg, 0.11 mmol), pyridine-3-carboxamide (20.6 mg, 0.17 mmol) and sodium hydride (6.8 mg, 0.17 mmol) were added to N,N-dimethylformamide (3 mL), and the mixture was stirred at 80°C for 12 hours. After the reaction was completed, 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 by column chromatography to obtain the target compound 287 (39.4 mg, 82%).

[0975] 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).

[0976] MS (ESI, LR) calculated value C 24 H 23 N6O2[M+H] + :427.2, measured value:427.1.

[0977] Example 316. 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[0978] Example 355. (7-(6-(4-nitro-1H-pyrazol-1-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[0979] For Example 316 and Example 355, Compound 19 and the corresponding compound were used to obtain the compounds by the synthesis method used in Example 287. The structural data and spectral data are shown in Table 17 below.

[0980] [Table 17]

[0981]

[0982]

[0983] Example 301. N-(3-chloro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)nicotinamide

[0984] 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

[0985] For Example 301 and Example 311, Compound 289 and the corresponding compound were used to obtain the compounds by the synthesis method used in Example 287. The structural data and spectral data are shown in Table 18 below.

[0986] [Table 18]

[0987]

[0988]

[0989] Example 323. 3-(3-Fluoro-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[0990] 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

[0991] For Example 323 and Example 362, Compound 288 and the corresponding compound were used to obtain the compounds by the synthesis method used in Example 287. The structural data and spectral data are shown in Table 19 below.

[0992] [Table 19]

[0993]

[0994] Example 308. 3-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyrimidin-2-yl)oxazolidin-2-one

[0995]

[0996] The target compound 308 was obtained by the synthetic method of Example 287 using compound 267 and oxazolidin-2-one.

[0997] 1H 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).

[0998] MS (ESI, LR) calculated value C 20 H 21 N6O3[M+H] + :393.2, measured value: 393.1.

[0999] Example 257. (7-(2-(3-Fluoroazetidin-1-yl)pyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1000]

[1001] After obtaining an intermediate by the same synthesis method as Step 1-3 in Example 1 using Compound 1-2 and (2-fluoro-4-pyridyl)boronic acid, the target compound 257 was obtained by the synthesis method in Example 107 using azetidine.

[1002] 1 H 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).

[1003] MS (ESI, LR) calculated value C 21 H 23FN5O[M+H] + :380.2, measured value:380.1.

[1004] Example 112. N-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)methanesulfonamide

[1005] <Scheme 18>

[1006]

[1007] Compound 17 (0.1 g, 0.31 mmol) and triethylamine (97 μL, 0.7 mmol) were dissolved in dichloromethane (5 mL), the temperature was lowered to 0°C with ice water, and methanesulfonyl chloride (52 μL, 0.7 mmol) was added dropwise. The temperature was raised to room temperature, and the reaction mixture was stirred for 12 hours. After the reaction was complete, the reaction solution was diluted with dichloromethane (20 mL), washed with water (30 mL), saturated sodium bicarbonate aqueous solution (30 mL), and brine (30 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated using column chromatography to obtain the target compound 112 (29 mg, 24%).

[1008] 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).

[1009] MS (ESI, LR) calculated value C 20 H 22 N5O4S[M+H] + :400.1, measured value:400.0.

[1010] Example 113. (7-(3-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1011] <Scheme 19>

[1012]

[1013] 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 by column chromatography to obtain the target compound 113 (7 mg, 6%).

[1014] 1 H 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).

[1015] MS (ESI, LR) calculated value C 20 H 20 N 7 O[M+H] + :374.2, measured value:374.2.

[1016] Example 114. (7-(4-(1H-tetrazol-5-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1017]

[1018] The target compound 114 was obtained by the synthesis method of Example 113 using compound 15 and the corresponding compound.

[1019] 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).

[1020] MS (ESI, LR) calculated value C 20 H 20 N7O[M+H] +:374.2, measured value:374.2.

[1021] Example 115. 3-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

[1022] <Scheme 20>

[1023]

[1024] Step 115-1: Compound 6 (0.15 g, 0.45 mmol) was dissolved in ethanol (6.5 mL), hydroxylamine (47 mg, 0.68 mmol) was added, and the mixture was 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 obtain the target compound 115-1 (0.079 g, 24%).

[1025] 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 and stirred at room temperature for 30 minutes. The temperature was raised to 80°C and stirred for 1 hour. After the reaction was completed, the reaction solution was concentrated and separated by column chromatography to obtain the target compound 115 (0.093 g, 43%).

[1026] 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).

[1027] MS (ESI, LR) calculated value C 21 H 20 N5O3[M+H] + :390.2, measured value:390.1.

[1028] Example 116. 3-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)-1,2,4-oxadiazol-5(4H)-one

[1029] 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

[1030] Example 247. 3-[3-Fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]-4H-1,2,4-oxadiazol-5-one

[1031] 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

[1032] 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

[1033] 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

[1034] 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

[1035] 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

[1036] 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

[1037] 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

[1038] 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

[1039] For Examples 116, 117, 247, 275, 295, 297, 299, 304, 321, 329, and 331, Compound 1-2 and the corresponding compound were used, sequentially following the synthetic methods of Steps 1-3 of Example 1 and the synthetic method of Example 115 to obtain the compounds. The structural and spectral data are shown in Table 20 below.

[1040] [Table 20]

[1041]

[1042]

[1043]

[1044] Example 118. (7-(4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1045] <Scheme 21>

[1046]

[1047] Compound 116-1 (0.014 g, 0.038 mmol) was dissolved in pyridine (2 mL), and acetyl chloride (5.5 μL, 47 mg, 0.077 mmol) was added, followed by stirring 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 x 2) and brine (10 mL x 2). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography to obtain the target compound 118 (5.4 mg, 36%).

[1048] 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).

[1049] MS (ESI, LR) calculated value C 22 H 22 N5O2[M+H] + :388.2, measured value:388.1.

[1050] Example 263. [7-[5-Fluoro-6-(5-methyl-1,2,4-oxadiazol-3-yl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1051] Example 276. [7-[4-Fluoro-3-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1052] Example 296. [7-[2-Fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1053] Example 303. [7-[3-Fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1054] Example 317. [7-[2-(5-methyl-1,2,4-oxadiazol-3-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1055] 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

[1056] 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

[1057] 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

[1058] 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

[1059] For Examples 263, 276, 296, 303, 317, 319, 322, 328, and 330, Compound 1-2 and the corresponding compound were obtained by sequentially following the same synthesis method as in Step 159-3 of Example 159, the synthesis method in Step 115-1 of Example 115, and the synthesis method of Example 118. The structural and spectral data are shown in Table 21 below.

[1060] [Table 21]

[1061]

[1062]

[1063] Example 352. [7-[4-(1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1064] <Scheme 22>

[1065]

[1066] Compound 116-1 (50 mg, 0.14 mmol) was added to trimethyl orthoformate (0.13 mL, 0.78 mmol) and stirred at 100° C. for 16 hours. The reaction solution was concentrated and separated by column chromatography to obtain the target compound 352 (35 mg, 65%).

[1067] 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).

[1068] MS (ESI, LR) calculated value C 21 H 20 N5O2[M+H] + :374.2, measured value: 374.1.

[1069] Example 341. (7-(3-Fluoro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1070] Example 342. (7-(3-nitro-5-(1,2,4-oxadiazol-3-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1071] Example 374. (7-(5-(1,2,4-oxadiazol-3-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1072] For Examples 341, 342, and 374, Compounds 1-2 and corresponding compounds were obtained by sequentially following the same synthesis methods as in Step 159-3 of Example 159, the synthesis method in Step 115-1 of Example 115, and the synthesis method of 352. The structural and spectral data are shown in Table 22 below.

[1073] [Table 22]

[1074]

[1075]

[1076] Example 361. 1-Piperidinyl-[7-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[1077] <Scheme 23>

[1078]

[1079] Compound 116-1 (0.040 g, 0.11 mmol) was dissolved in tetrahydrofuran (2 mL), trifluoroacetic anhydride (15.3 μL, 23 mg, 0.11 mmol) was added, and the mixture was stirred at 80°C for 16 hours. After completion of the reaction, the reaction solution was diluted with dichloromethane (10 mL) and washed with water (10 mL x 2) and brine (10 mL x 2). The organic layer was dried over anhydrous magnesium sulfate, filtered, concentrated, and separated by column chromatography to obtain the target compound 361 (45 mg, 92%).

[1080] 1H 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).

[1081] MS (ESI, LR) calculated value C 22 H 19 F3N5O2[M+H] + :442.1, measured value:442.1.

[1082] Example 359. [7-[4-(5-amino-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1083] <Scheme 24>

[1084]

[1085] Step 359-1: Compound 116-1 and trichloroacetic anhydride were used to obtain the target compound 359-1 by the synthesis method of Example 361.

[1086] Step 359-2: 7N ammonia methanol solution (1.6 mL, 11.2 mmol) was added to compound 359-1 (130 mg, 0.26 mmol) and stirred at room temperature for 16 hours. After the reaction solution was concentrated, it was separated by column chromatography to obtain the target compound 359 (92 mg, 89%).

[1087] 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).

[1088] MS (ESI, LR) calculated value C 21 H 21 N6O2[M+H] +:389.2, measured value:389.1.

[1089] Example 348. [7-[4-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1090] <Scheme 25>

[1091]

[1092] Step 348-1: Compound 10 (120 mg, 0.34 mmol) was dissolved in dichloromethane (4 mL), tert-butyl carbazate (49.9 mg, 0.38 mmol) and EDC·HCl (72.4 mg, 0.38 mmol) were added, and stirred for 1 hour. After completion of the reaction, the mixture was diluted with dichloromethane (10 mL), washed with aqueous sodium bicarbonate solution and brine, dried over anhydrous magnesium sulfate, filtered, and concentrated to obtain compound 348-1 (151 mg, 95%).

[1093] Step 348-2: Compound 348-1 (220 g, 0.47 mmol) was placed in a reaction vessel and the temperature was lowered to 0°C. Trifluoroacetic acid (1 mL, 13.1 mmol) was added and stirred for 1 hour. After the reaction was complete, it was concentrated, diluted with ether (10 mL), recrystallized, and filtered. The filtrate was dissolved in aqueous sodium bicarbonate and extracted with dichloromethane. Drying was performed over anhydrous magnesium sulfate, filtering, and concentrating to afford compound 348-2 (140 mg, 65%).

[1094] Step 348-3: Add N,N-dimethylformamide (2 mL) to the reaction vessel, add 4N hydrochloric acid (0.1 mL, 0.41 mmol) dissolved in 1,4-dioxane, and stir for 5 minutes. Add imidazole (28.1 mg, 0.41 mmol), stir for 30 minutes, add compound 348-2 (50 mg, 0.14 mmol), and stir at 100°C for 16 hours. Add phosphorus oxychloride (15.4 μL, 0.17 mmol), and stir for 12 hours. After the reaction is complete, cool to room temperature, dilute with brine (5 mL), and extract with dichloromethane (5 mL x 3). The combined organic layers are dried over anhydrous magnesium sulfate, filtered, concentrated, and recrystallized from N,N-dimethylformamide, filtered, and dried to obtain the target compound 348 (14 mg, 26%).

[1095] 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=7.0,1.4Hz,1H),3.63(t,J=5.4Hz,4H),2.63(s,3H),1.66(s,2H),1.62-1.53(m,4H).

[1096] MS (ESI, LR) calculated value C 22 H 22 N5O2[M+H] + :388.2, measured value:388.1.

[1097] Example 364. [7-[6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1098] Example 379. [7-[5-Fluoro-6-(5-methyl-1,3,4-oxadiazol-2-yl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1099] For Examples 364 and 379, the corresponding compounds were obtained by sequentially following the same synthesis method as in Step 159-3 of Example 159 and the same synthesis method as in Example 348. The structural and spectral data are shown in Table 23 below.

[1100] [Table 23]

[1101]

[1102]

[1103] Example 350. [7-[4-(1,3,4-oxadiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1104] Example 380. [7-[5-Fluoro-6-(1,3,4-oxadiazol-2-yl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1105] For Examples 350 and 380, Compound 10 and Compound 243 were used in sequence using the same synthesis method as in Steps 348-1 and 348-2 of Example 348 and Example 352 to obtain the compounds. The structural and spectral data are shown in Table 24 below.

[1106] [Table 24]

[1107]

[1108] Example 365. 1-Piperidinyl-[7-[6-(2-thioxo-3H-1,3,4-oxadiazol-5-yl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[1109] <Scheme 26>

[1110]

[1111] Step 365-1: Compound 1-2 was used to obtain the target compound 365-1 by the same synthesis method as Step 1-3 in Example 1.

[1112] Step 365-2: Compound 365-1 was used to obtain the target compound 365-2 by the same synthesis method as Step 243-1 of Example 243.

[1113] Step 365-3: Compound 365-2 was used to obtain the target compound 365-3 by the same synthesis method as Step 348-1 of Example 348.

[1114] Step 365-4: Compound 365-3 was used to obtain the target compound 365-4 by the same synthesis method as Step 348-2 of Example 348.

[1115] Step 365-5: Compound 365-4 (70 mg, 0.15 mmol) was dissolved in 1,4-dioxane (2 mL), and bis(imidazol-1-yl)methanethiol (39.5 mg, 0.22 mmol) and DBU (88 μL, 0.59 mmol) were added. The mixture was stirred at 100°C for 16 hours. After completion of the reaction, the reaction solution was concentrated and separated by column chromatography to obtain the target compound 365 (57 mg, 95%).

[1116] 1H 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).

[1117] MS (ESI, LR) calculated value C 20 H 19 N6O2S[M+H] + :407.1, measured value:407.1.

[1118] Example 394. [7-[5-Fluoro-6-[5-(trifluoromethyl)-1,3,4-oxadiazol-2-yl]-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1119] <Scheme 27>

[1120]

[1121] Step 394-1: Compound 243 was used to obtain the target compound 394-1 by the same synthesis method as Steps 348-1 and 348-2 of Example 348.

[1122] Step 394-2: Compound 394-1 was used to obtain the target compound 394-2 by the same synthesis method as Example 361.

[1123] Step 394-3: Compound 394-2 (75 mg, 0.15 mmol) was dissolved in 1,4-dioxane (2 mL), phosphorus oxychloride (0.15 mL, 1.5 mmol) was added, and stirred at 100°C for 16 hours. After the reaction was completed, the reaction solution was concentrated, diluted with dichloromethane (5 mL), and the pH of the solution was adjusted to 9 with aqueous sodium bicarbonate solution. After extraction with dichloromethane (5 mL × 3), the combined organic solution was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated. The residue was separated by column chromatography to obtain the target compound 394 (7 mg, 9.2%).

[1124] 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).

[1125] MS (ESI, LR) calculated value C 21 H 17 F4N6O2[M+H] + :461.1, measured value:461.1.

[1126] Example 349. 5-[4-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]-3H-1,3,4-oxadiazol-2-one

[1127] <Scheme 28>

[1128]

[1129] Compound 348-2 (50 mg, 0.14 mmol) was dissolved in tetrahydrofuran (2 mL), and DIPEA (48 μL, 0.28 mmol) and triphosgene (16.3 mg, 0.05 mmol) were added, followed by stirring at 80° C. for 1 hour. After completion of the reaction, the reaction solution was concentrated and separated by column chromatography to obtain the target compound 349 (30 mg, 53%).

[1130] 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).

[1131] MS (ESI, LR) calculated value C 21 H 20 N5O3[M+H] + :390.1, measured value:390.1.

[1132] Example 360.5-[5-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]-3H-1,3,4-oxadiazol-2-one

[1133] Example 3735-[3-Fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]-3H-1,3,4-oxadiazol-2-one

[1134] For Example 360 ​​and Example 373, the corresponding compounds were used to obtain the compounds by the same synthesis method as Example 349. The structural data and spectral data are shown in Table 25 below.

[1135] [Table 25]

[1136]

[1137] Example 300. [7-[4-(2-Methylpyrazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1138] Example 302. [7-[4-(3-Furyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1139] Example 305. 5-[4-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carbonitrile

[1140] Example 306. [7-[4-(2-Hydroxypyrimidin-5-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1141] Example 307. 5-[4-[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]phenyl]pyrimidine-2-carboxamide

[1142] Example 324. [7-[4-(3,5-Dimethylisoxazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1143] Example 346. 1-Piperidinyl-[7-[4-(1H-pyrazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[1144] Example 347. 1-Piperidinyl-[7-[4-(3-thienyl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone

[1145] For Examples 300, 302, 305, 306, 307, 324, 346, and 347, Compound 292 and the corresponding compound were used to obtain the compounds by the same synthesis method as in Steps 1-3 of Example 1. The structural data and spectral data are shown in Table 26 below.

[1146] [Table 26]

[1147]

[1148]

[1149]

[1150] Example 351. [7-[4-(5-Methylthiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1151] <Scheme 29>

[1152]

[1153] Step 351-1: Compound 292 (0.370 g, 0.96 mmol) was dissolved in N,N-dimethylformamide (10 mL), and bis(pinacolato)diboron (0.366 g, 1.44 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.040 g, 0.05 mmol) and potassium acetate (0.283 g, 2.89 mmol) were added. The reaction solution was bubbled with nitrogen for 10 minutes and stirred at 90 ° C for 16 hours. After the reaction was completed, the temperature was lowered to room temperature, diluted with dichloromethane (10 mL), and palladium was removed with diatomaceous earth (Celite). The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was separated by column chromatography to obtain the target compound 351-1 (0.528 g, 57%).

[1154] Step 351-2: Compound 351-1 and 2-bromo-5-methyl-thiazole were used to obtain the target compound 351 by the same synthesis method as Step 159-3 of Example 159.

[1155] 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

[1156] =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).

[1157] MS (ESI, LR) calculated value C 23 H 23 N4OS[M+H] + :403.2, measured value:403.1.

[1158] Example 358. 7-[4-(1,2-dimethylimidazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1159]

[1160] The target compound 358 was obtained by the same synthesis method as in Step 351-2 in Example 351 using Compound 351-1 and 4-bromo-1,2-dimethyl-imidazole.

[1161] 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).

[1162] MS (ESI, LR) calculated value C 24 H 26 N5O[M+H] + :400.2, measured value:400.1.

[1163] 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

[1164]

[1165] Compound 330 was used to obtain the target compound 343 by the same synthesis method as in Example 7.

[1166] 1H 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).

[1167] MS (ESI, LR) calculated value C 22 H 23 N6O2[M+H] + :403.2, measured value:403.1.

[1168] Example 119. (Z)-5-(3-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzylidene)thiazolidine-2,4-dione

[1169] <Scheme 30>

[1170]

[1171] Step 119-1: Compound 1-2 and 3-formylphenylboronic acid were used to obtain the target compound 119-1 by the same synthesis method as Step 1-3 in Example 1.

[1172] Step 119-2: Compound 119-1 (0.15 g, 0.45 mmol) and thiazolidine-2,4-dione (0.063 g, 0.54 mmol) were dissolved in ethanol (5 mL). Piperidine (35 μL, 0.36 mmol) was added, and the mixture was stirred at 80°C for 16 hours. After the reaction was complete, the temperature was lowered to room temperature, the mixture was diluted with water (5 mL), and acidified with 1N citric acid (pH 4) to obtain a precipitated solid. The solid was filtered and washed sequentially with water, diethyl ether, and methyl tert-butyl ether to obtain the target compound 119 (50 mg, 25%).

[1173] 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,2H) ,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).

[1174] MS (ESI, LR) calculated value C 23 H 21 N4O3S[M+H] + :433.1, measured value:433.1.

[1175] Example 253. 3-(3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzaldehyde oxime

[1176]

[1177] The target compound 253 was obtained using compound 119-1 through the synthetic method of step 236-2 of Example 236.

[1178] 1 H 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).

[1179] MS (ESI, LR) calculated value C 20 H 21 N4O2[M+H] + :349.2, measured value:349.1.

[1180] Example 132. 2-Methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1181] <Scheme 31>

[1182]

[1183] Compound 131 (30 mg, 0.08 mmol) was dissolved in N,N-dimethylformamide (3 mL), the temperature was lowered to 0 ° C, and sodium hydride (60%, 8 mg, 0.2 mmol) was added. The reaction solution was stirred at room temperature for 15 minutes, iodomethane (7.5 μL, 0.12 mmol) was added, and the mixture was stirred for 1 hour. After the reaction was completed, the temperature was lowered to 0 ° C, the reaction solution was diluted with water (10 mL), and extracted with dichloromethane (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%).

[1184] 1 H NMR (400MHz, 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), 7.5 5-7.45(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).

[1185] MS (ESI, LR) calculated value C 23 H 25 N4O2[M+H] + :389.2, measured value:389.2.

[1186] 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

[1187]

[1188] The target compound 199 was obtained by the synthesis method of Example 132 using compound 195 and the corresponding compound.

[1189] 1H 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).

[1190] MS (ESI, LR) calculated value C 22 H 24 N5O2[M+H] + :390.2, measured value:390.1.

[1191] Example 133. 2-Isopropyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1192] <Scheme 32>

[1193]

[1194] The target compound 133 was obtained using compound 131 and iodisopropyl by the synthesis method of Example 132.

[1195] 1 H NMR (400MHz, DMSO-d6) δ (ppm): 8.41 (d, J = 2.0 Hz, 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).

[1196] MS (ESI, LR) calculated value C 25 H 29 N4O2[M+H] + :417.2, measured value:417.1.

[1197] Example 135. 2-Methyl-7-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one

[1198]

[1199] The target compound 135 was obtained by the synthesis method of Example 132 using compound 134 and iodomethane.

[1200] 1 H NMR (400MHz, DMSO-d6) δ (ppm): 8.80 (d, J = 1.9 Hz, 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).

[1201] MS (ESI, LR) calculated value C 23 H 23 N4O2[M+H] + :387.2, measured value:387.1.

[1202] Example 137. 2-Methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1203]

[1204] The target compound 137 was obtained by the synthesis method of Example 132 using compound 136 and iodomethane.

[1205] 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).

[1206] MS (ESI, LR) calculated value C 23 H 25 N4O2[M+H] + :389.2, measured value:389.1.

[1207] Example 139. 2-Methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoquinolin-1(2H)-one

[1208]

[1209] The target compound 139 was obtained by the synthesis method of Example 132 using compound 138 and iodomethane.

[1210] 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).

[1211] MS (ESI, LR) calculated value C 23 H 23 N4O2[M+H] + :387.2, measured value:387.1.

[1212] Example 141. 2-Methyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1213]

[1214] The target compound 141 was obtained by using compound 140 and iodomethane according to the synthesis method of Example 132.

[1215] 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).

[1216] MS (ESI, LR) calculated value C 22 H 23 N4O2[M+H] + :375.2, measured value:375.1.

[1217] Example 142. 2-Isopropyl-6-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1218]

[1219] The target compound 142 was obtained by using compound 140 and iodisopropyl ether according to the synthesis method of Example 132.

[1220] 1 H 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).

[1221] MS (ESI, LR) calculated value C 24 H 27 N4O2[M+H] +:403.2, measured value:403.1.

[1222] Example 144. 2-Methyl-5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1223]

[1224] The target compound 144 was obtained by the synthesis method of Example 132 using compound 143 and iodomethane.

[1225] 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).

[1226] MS (ESI, LR) calculated value C 22 H 23 N4O2[M+H] + :375.2, measured value:375.1.

[1227] Example 259. [7-(3-Amino-1,2-benzoxazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1228] <Scheme 33>

[1229]

[1230] Potassium tert-butyrate (64.4 mg, 0.57 mmol) and acetohydroxamic acid (43.1 mg, 0.57 mmol) were dissolved in N,N-dimethylformamide (3 mL) and stirred for 20 minutes. Compound 254 (100 mg, 0.29 mmol) was added and stirred for 1 hour, then the temperature was raised to 60 ° C and stirred for 1 hour. After the reaction was completed, the temperature of the reaction solution was lowered to room temperature, water was added, and filtered. The filtrate was separated by column chromatography to obtain the target compound 259 (36 mg, 33%).

[1231] 1H 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).

[1232] MS (ESI, LR) calculated value C 20 H 20 N5O2[M+H] + :362.2, measured value:362.1.

[1233] Example 320. [7-(3-Amino-1,2-benzoxazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1234]

[1235] Using compound 22, the target compound 320 was obtained by the synthesis method of Example 259.

[1236] 1 HNMR (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).

[1237] MS (ESI, LR) calculated value C 20 H 20 N5O2[M+H] + :362.2, measured value:362.1.

[1238] Example 260. [7-(3-Amino-1H-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1239] <Scheme 34>

[1240]

[1241] Compound 254 (100 mg, 0.29 mmol) was dissolved in ethanol (3 mL), hydrazine hydrate (35.9 mg, 0.57 mmol) was added, and the mixture was stirred at 150° C. in a microwave reactor for 35 minutes. The reaction solution was concentrated, diluted with water, and filtered. The filtrate was separated by column chromatography to obtain the target compound 260 (85 mg, 33%).

[1242] 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).

[1243] MS (ESI, LR) calculated value C 20 H 21 N6O[M+H] + :361.2, measured value:361.1.

[1244] Example 309. [7-(3-Amino-1H-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1245]

[1246] Using compound 22, the target compound 309 was obtained by the synthesis method in Example 260.

[1247] 1 H 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).

[1248] MS (ESI, LR) calculated value C 20 H 21 N6O[M+H] + :361.2, measured value:361.1.

[1249] Example 261. [7-(3-Amino-1-methyl-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1250] Example 310. [7-(3-Amino-1-methyl-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1251] Example 261 and Example 310 were obtained from Compound 254 and Compound 22, respectively, using methylhydrazine by the same synthesis method as Example 260. The structural and spectral data are shown in Table 27 below.

[1252] [Table 27]

[1253]

[1254] 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

[1255] <Scheme 35>

[1256]

[1257] Step 395-1: Using compound 1-2 and 2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazol-1-yl]acetonitrile, the synthesis method in step 159-3 of Example 159 was used to obtain the target compound 395-1.

[1258] Step 395-2: Compound 395-1 and DIPEA were used to obtain the target compound 395-2 by the synthetic method in Step 115-1 of Example 115.

[1259] Step 395-3: To compound 395-2 (100 mg, 0.27 mmol) were added trimethyl orthoformate (1.49 mL, 13.6 mmol) and trifluoroacetic acid (8.3 μL), and the mixture was stirred at 60°C for 1 hour. After the reaction was complete, 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 by column chromatography to obtain the target compound 395 (39 mg, 38%).

[1260] 1 H 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).

[1261] MS (ESI, LR) calculated value C 19 H 20 N7O2[M+H] + :378.2, measured value:378.1.

[1262] 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

[1263]

[1264] Compound 395-5 was used to obtain the target compound 396 by the synthesis method of Example 349.

[1265] 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).

[1266] MS (ESI, LR) calculated value C 19 H 20N7O3[M+H] + :394.2, measured value:394.1.

[1267] 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

[1268] <Scheme 36>

[1269]

[1270] Step 397-1: Compound 1-2 was used to obtain the target compound 397-1 through the synthesis method in Step 159-3 of Example 159.

[1271] Step 397-2: Compound 397-1 was used to obtain the target compound 397-2 by the synthesis method in Step 395-1 of Example 395.

[1272] Step 397-3: Compound 397-2 was used to obtain the target compound 397-3 by the synthetic method in Step 395-2 of Example 395.

[1273] Step 397-4: Compound 397-3 was used to obtain the target compound 397 by the synthetic method in Step 395-3 of Example 395.

[1274] 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).

[1275] MS (ESI, LR) calculated value C 24 H 23 N8O2[M+H] + :455.2, measured value:455.1.

[1276] Example 146. 4-((3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)benzonitrile

[1277] <Scheme 37>

[1278]

[1279] Compound 1-2 (0.05 g, 0.14 mmol), palladium acetate (1.58 mg, 0.007 mmol), BINAP (8.7 mg, 0.01 mmol) and cesium carbonate (183.4 mg, 0.56 mmol) were dissolved in 1,4-dioxane (2 mL). After nitrogen was introduced, the mixture was stirred at 100 ° C for 16 hours. After the reaction was completed, 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 separated by column chromatography to obtain the target compound 146 (16 mg, 32%). [BINAP (2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)]

[1280] 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).

[1281] MS (ESI, LR) calculated value C 20 H 20 N5O[M+H] + :346.2, measured value:346.1.

[1282] Example 147. 3-((3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)amino)pyridin-2(1H)-one

[1283] Example 148. Piperidin-1-yl(7-((pyrimidin-2-ylmethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone

[1284] Example 149. Piperidin-1-yl(7-((2-(pyridin-4-yl)ethyl)amino)pyrazolo[1,5-a]pyridin-3-yl)methanone

[1285] Example 150. (7-((1-Methylpiperidin-4-yl)amino)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1286] Example 211. 7-[[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-3,4-dihydro-2H-isoquinolin-1-one

[1287] Example 212. 6-[[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]isoindolin-1-one

[1288] Example 238. [7-[(4-Chlorophenyl)methylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1289] Example 242. [7-[2-(4-Chlorophenyl)ethylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1290] For Examples 147, 148, 149, 150, 211, 212, 238, and 242, Compound 1-2 and the corresponding compound were used to obtain the compounds by the synthesis method described in Example 146. The structural and spectral data are shown in Table 28 below.

[1291] [Table 28]

[1292]

[1293]

[1294]

[1295] Example 194. (7-((3-Methoxyphenyl)thio)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1296] <Scheme 38>

[1297]

[1298] 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-dioxane (2 mL), and the mixture was stirred at 100° C. for 1 hour after being filled with nitrogen. After the reaction was completed, 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 by column chromatography to obtain the target compound 194 (61 mg, 98%).

[1299] 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).

[1300] MS (ESI, LR) calculated value C 20 H 22 N3O2S[M+H] + :368.1, measured value:368.1.

[1301] Example 235. 4-[[3-(Piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]-1H-pyrimidin-6-one

[1302]

[1303] The target compound 235 was obtained by the synthesis method of Example 194 using compound 1-2, palladium acetate and the corresponding compound.

[1304] 1H 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).

[1305] MS (ESI, LR) calculated value C 17 H 19 N6O2[M+H] + :339.1, measured value:339.1.

[1306] Example 236. 3-Methyl-6-[[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]amino]pyrimidin-4-one

[1307] <Scheme 39>

[1308]

[1309] Step 236-1: Compound 236-1 was obtained by the synthesis method of Example 146 using compound 1-2 and benzophenone imine.

[1310] 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 separated by column chromatography to obtain the target compound 236-2 (845 mg, 69%).

[1311] Step 236-3: Using compound 236-2 and 6-bromo-3-methyl-pyrimidin-4-one, the target compound 236 was obtained by the synthesis method in Example 235.

[1312] 1 H 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).

[1313] MS (ESI, LR) calculated value C 18 H 21N6O2[M+H] + :353.2, measured value:353.1.

[1314] Example 239. 4-Chloro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzamide

[1315] <Scheme 40>

[1316]

[1317] Compound 236-2 (70 mg, 0.28 mmol) was dissolved in pyridine (2.6 mL), dimethylaminopyridine (17.5 mg, 0.14 mmol) and 4-chlorobenzoyl chloride (75.2 mg) were added, and the mixture was stirred at room temperature for 16 hours. The reaction solution was concentrated, and the residue was separated by column chromatography to obtain the target compound 239 (60 mg, 53%).

[1318] 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).

[1319] MS (ESI, LR) calculated value C 20 H 20 ClN4O2[M+H] + :383.1, measured value:383.1.

[1320] Example 240. 1,3,5-Trimethyl-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrazole-4-sulfonamide

[1321] Example 241. 5-Fluoro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide

[1322] For Example 240 and Example 241, Compound 236-2 and the corresponding compound were used to obtain the compounds by the synthesis method of Example 239. The structural data and spectral data are shown in Table 29 below.

[1323] [Table 29]

[1324]

[1325]

[1326] Example 151. 1-(7-(Quinolin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)pentan-1-one

[1327] <Scheme 41>

[1328]

[1329] Step 151-1: Using pyrazolo[1,5-a]pyridine-3-carboxylic acid, the target compound 151-1 was obtained by the same synthesis method as Step 1-2 in Example 1.

[1330] Step 151-2: Compound 151-1 (1 g, 4.36 mmol) was dissolved in tetrahydrofuran (15 mL), the temperature was lowered to -78 ° C, and n-butyl lithium (2.5 M solution, 2.44 mL, 6.1 mmol) was slowly added. After stirring the reaction solution for 30 minutes, 1,2-iodoethane (1.47 g, 5.23 mmol) dissolved in tetrahydrofuran (9 mL) was added. After stirring the reaction solution for 3 hours, the temperature was raised to room temperature, and the mixture was diluted with saturated sodium bicarbonate aqueous solution (20 mL) and dichloromethane (20 mL). The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was separated by column chromatography to obtain the target compound 151-2 (151 mg, 11%).

[1331] Step 151-3: Compound 151-2 was used to obtain the target compound 151 by the same synthesis method as Step 1-3 in Example 1.

[1332] 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).

[1333] MS (ESI, LR) calculated value C 21 H 20 N3O[M+H] + :330.2, measured value:330.2.

[1334] Example 152. 4-(3-acetylpyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[1335] <Scheme 42>

[1336]

[1337] Step 152-1: Using pyrazolo[1,5-a]pyridine-3-carboxylic acid and 4-cyanophenylboronic acid, the target compound 152-1 was obtained by the same synthesis method as Step 1-3 in Example 1.

[1338] Step 152-2: Compound 152-1 and dimethylhydroxylamine were used to obtain the target compound 152-2 by the same synthesis method as Step 1-2 in Example 1.

[1339] Step 152-3: Compound 152-2 (0.05 mg, 0.16 mmol) was dissolved in tetrahydrofuran (2 mL), the temperature was lowered to 0°C, and methylmagnesium bromide (3 M solution, 0.1 mL, 0.33 mmol) was slowly added. The reaction solution was stirred for 3 hours, diluted with saturated aqueous ammonium chloride (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 separated by column chromatography to obtain the target compound 152 (11 mg, 24%).

[1340] 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).

[1341] MS (ESI, LR) calculated value C 16 H 12 N3O[M+H] + :262.1, measured value:262.1.

[1342] Example 153. 4-(3-(2-hydroxypropan-2-yl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[1343] <Scheme 43>

[1344]

[1345] Using compound 152-2, the target compound 153 was obtained by the same synthesis method as step 152-3 in Example 152.

[1346] 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).

[1347] MS (ESI, LR) calculated value C 17 H 15 N2O2[M+H] + :279.1, measured value:279.1.

[1348] Example 154. 7-(3-(4-Fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1349] <Scheme 44>

[1350]

[1351] Step 154-1: Compound 1-1 and 4-fluoropiperidine were used to obtain the target compound 154-1 by the same synthesis method as Step 1-2 in Example 1.

[1352] Step 154-2: Using compound 154-1 and 7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydro-2H-isoquinolin-1-one, the target compound 154 was obtained by the same synthesis method as steps 1-3 in Example 1.

[1353] 1H 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).

[1354] MS (ESI, LR) calculated value C 22 H 22 FN4O2[M+H] + :393.2, measured value: 393.1.

[1355] Example 155. 6-(3-(4-Fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1356] Example 156. 4-(3-(4-Fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)benzonitrile

[1357] Example 157. (4-Fluoropiperidin-1-yl)(7-(4-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[1358] Example 231. 6-(3-(4-Fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methylisoindolin-1-one

[1359] For Examples 155, 156, 157, and 231, Compound 154-1 and the corresponding compound were used to obtain the compounds by the same synthesis method as Steps 1-3 in Example 1. The structural and spectral data are shown in Table 30 below.

[1360] [Table 30]

[1361]

[1362] Example 158. Cyclohexyl(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[1363] <Scheme 45>

[1364]

[1365] 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 synthesis method as Step 1-3 in Example 1.

[1366] Step 158-2: Compound 158-1 and dimethylhydroxylamine were used to obtain the target compound 158-2 by the same synthesis method as Step 1-2 in Example 1.

[1367] Step 158-3: Compound 158-2 and cyclohexylmagnesium bromide were used to obtain the target compound 158 by the same synthesis method as Step 152-3 in Example 152.

[1368] 1 H 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).

[1369] MS (ESI, LR) calculated value C 20 H 21 N2O[M+H] + :305.2, measured value:305.1.

[1370] Example 227. (2-Azabicyclo[2.2.1]heptan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[1371] Example 228. (2-Azabicyclo[2.2.2]octan-2-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[1372] Example 229. (7-Azabicyclo[2.2.1]heptan-7-yl)(7-phenylpyrazolo[1,5-a]pyridin-3-yl)methanone

[1373] For Example 227, Example 228, and Example 229, Compound 158-1 and the corresponding compound were used to obtain the compounds by the same synthesis method as Step 1-2 in Example 1. The structural data and spectral data are shown in Table 31 below.

[1374] [Table 31]

[1375]

[1376]

[1377] Example 234. 6-(3-(4,4-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1378] Example 378. 6-(3-(3-Fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1379] Example 382. 6-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1380] Example 385. (R)-6-(3-(3-Methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1381] Example 386. (S)-6-(3-(3-Methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1382] Example 387. 6-(3-(3-Methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1383] Example 390. 6-(3-(2-Azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1384] Example 391. 6-(3-(6-Azaspiro[3.4]octane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1385] Example 392. 6-(3-(7-Azaspiro[3.5]nonane-7-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1386] Example 393. 6-(3-(3-ethylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1387] Example 398. 6-(3-(3-(Trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1388] Example 400. 6-(3-(3-Isopropylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1389] Example 401. 6-(3-(1,2,3,6-tetrahydropyridine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1390] Example 405. 6-(3-(6-Azaspiro[3.5]nonane-6-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1391] Example 411. 6-(3-(6-Fluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1392] Example 412. 6-(3-(6,6-difluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one

[1393] For Examples 234, 378, 382, ​​385, 386, 387, 390, 391, 392, 393, 398, 400, 401, 405, 411, and 412, an intermediate was obtained using Compound 1-1 and a corresponding compound by the same synthesis method as in Step 1-2 of Example 1, and then a compound was obtained using 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoindolin-1-one by the same synthesis method as in Step 1-3 of Example 1. The structural data and spectral data are shown in Table 32 below.

[1394] [Table 32]

[1395]

[1396]

[1397]

[1398]

[1399] Example 336. (7-(6-Fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-methylpiperidin-1-yl)methanone

[1400] Example 337. (3-Ethylpiperidin-1-yl)(7-(6-fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)methanone

[1401] Example 338. (7-(6-Fluoropyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(3-(trifluoromethyl)piperidin-1-yl)methanone

[1402] For Example 336, Example 337, and Example 338, the intermediate was obtained using Compound 1-1 and the corresponding compound by the same synthesis method as in Step 1-2 of Example 1, and then the compound was obtained using (6-fluoro-3-pyridyl)boronic acid by the same synthesis method as in Step 1-3 of Example 1. The structural data and spectral data are shown in Table 33 below.

[1403] [Table 33]

[1404]

[1405] Example 339. 3-(5-(3-(3-(trifluoromethyl)piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1406] Example 353. 3-(5-(3-(3-methylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1407] Example 354. 3-(5-(3-(3-ethylpiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1408] Example 383. 3-(5-(3-(3-fluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1409] Example 384. 3-(5-(3-(3,3-difluoropiperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)oxazolidin-2-one

[1410] For Examples 339, 353, 354, 383, and 384, compound 1-1 and the corresponding compound were used to obtain an intermediate by the same synthesis method as in Steps 1-2 of Example 1, and then the compound was obtained by the same synthesis method as in Example 316. The structural data and spectral data are shown in Table 34 below.

[1411] [Table 34]

[1412]

[1413]

[1414]

[1415] Example 340. N-(2-Nitrobenzyl)-N-(4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)phenyl)nicotinamide

[1416]

[1417] The target compound 340 was obtained by the synthesis method of Example 132 using compound 101 and the corresponding compound.

[1418] 1 H 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).

[1419] MS (ESI, LR) calculated value C 32 H 29 N6O4[M+H] + :561.2, measured value:561.1.

[1420] 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

[1421] <Scheme 46>

[1422]

[1423] Step 356-1: Using compound 1-2 and 2-bromo-6-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine, the target compound 356-1 was obtained by the same synthesis method as step 159-3 in Example 159.

[1424] Step 356-2: Compound 356-1 was used to obtain the target compound 356 by the synthesis method of Example 344.

[1425] 1 H 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).

[1426] MS (ESI, LR) calculated value C 21 H 21 BrN7O[M+H] + :466.1, measured value:466.0.

[1427] 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

[1428]

[1429] The target compound 363 was obtained by the same synthesis method as Example 221 using compound 356-1.

[1430] 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).

[1431] MS (ESI, LR) calculated direct value C 22 H 25 BrN5O2[M+H] +:470.1, measured value:470.1.

[1432] Example 345. (7-(3-(3-Hydroxyazetidin-1-yl)-5-(isoxazol-4-yl)phenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1433] 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

[1434] Example 366. (7-(2-(Isoxazolyl-4-yl)-6-morpholinylpyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1435] Example 369. (7-(2-(1-methyl-1H-pyrazol-5-yl)-6-morpholinylpyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1436] Example 371. (7-(2-(3,5-Dimethylisoxazol-4-yl)-6-morpholinylpyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1437] Example 376. (7-(5'-Fluoro-6-morpholinyl-[2,3'-bipyridyl]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1438] Example 377. (7-(2-(2-methylpyrimidin-5-yl)-6-morpholinylpyridin-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1439] 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

[1440] 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

[1441] Example 370. 3-(5'-Fluoro-4-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-[2,3'-bipyridyl]-6-yl)oxazolidin-2-one

[1442] 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

[1443] Example 375. (7-(6-(3-(Dimethylamino)azetidin-1-yl)-5'-fluoro-[2,3'-bipyridyl]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1444] For Examples 345, 357, 366, 369, 371, 376, 377, 367, 368, 370, 372, and 375, intermediates were obtained using Compound 356-1 and corresponding compounds by the same synthesis method as in Step 356-2 of Example 356, and then compounds were obtained by using the method used to synthesize Example 344. Structural and spectral data are shown in Table 35 below.

[1445] [Table 35]

[1446]

[1447]

[1448]

[1449] 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

[1450]

[1451] The target compound 325 was obtained using compound 265 and (2-methylpyrazol-3-yl)boronic acid by the same synthesis method as in Step 159-3 of Example 159.

[1452] 1 H 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).

[1453] MS (ESI, LR) calculated value C 21 H 23 FN6O[M+H] + :405.2, measured value:405.1.

[1454] Example 381. [7-[6-(3,5-Dimethylisoxazol-4-yl)-5-fluoro-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1455] Example 399. [7-[2-(3,5-dimethylisoxazol-4-yl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone

[1456] For Examples 381 and 399, (3,5-dimethylisoxazol-4-yl)boronic acid was used to obtain the compounds from Compound 281 and Compound 267, respectively, using the same synthesis method as in Step 159-3 of Example 159. The structural and spectral data are shown in Table 36 below.

[1457] [Table 36]

[1458]

[1459]

[1460] 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-piperidinyl)methanone

[1461]

[1462] The target compound 404 was obtained using compound 404-1, [5-(difluoromethyl)-1,3,4-thiadiazol-2-yl]boronic acid and potassium carbonate by the same synthesis method as in Step 159-3 of Example 159.

[1463] 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).

[1464] MS (ESI, LR) calculated value C 20 H 18 F2N7O2S[M+H] + :458.1, measured value:458.1.

[1465] Example 159. 7-(2-amino-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-3,4-dihydroisoquinolin-1(2H)-one

[1466] <Scheme 47>

[1467]

[1468] Step 159-1: Compound 159-1 (synthesized by reference to “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 prepared by the same synthesis method as in Step 1-2 of Example 1 to obtain the target compound 159-2.

[1469] Step 159-2: Compound 159-2 was used to obtain the target compound 159-3 by the same synthesis method as in Step 1-1 in Example 1.

[1470] Step 159-3: After dissolving compound 159-3 (0.118 g, 0.25 mmol) in 1,4-dioxane (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) and [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium (0.021 g, 0.03 mmol) were added to a 2M aqueous solution of cesium carbonate (0.38 mL, 0.75 mmol). Nitrogen was added to the reaction solution and stirred at 100 ° C for 12 hours. After the reaction was completed, the temperature was lowered to room temperature, diluted with dichloromethane (10 mL), and palladium was removed with diatomaceous earth (Celite). The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was separated using column chromatography to obtain the target compound 159-4 (117 mg, 95%).

[1471] Step 159-4: To compound 159-4 (50 mg, 0.1 mmol) was added a 4N 1,4-dioxane hydrochloric acid solution (2.56 mL), and the mixture was stirred for 2 hours. After completion of the reaction, the reaction solution was concentrated and separated by column chromatography to obtain the target compound 159 (25.1 mg, 63%).

[1472] 1 HNMR (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).

[1473] MS (ESI, LR) calculated value C 22 H 24 N5O2[M+H] + :390.2, measured value:390.2.

[1474] Example 160. 7-(2-amino-3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one

[1475] <Scheme 48>

[1476]

[1477] Step 160-1: Compound 159-4 (0.078 g, 0.16 mmol) was dissolved in N,N-dimethylformamide (3 mL), and iodomethane (11.8 μL, 0.19 mmol) and cesium carbonate (0.062 g, 0.19 mmol) were added and stirred for 12 hours. After the reaction was completed, the mixture was filtered through Celite and washed with ethyl acetate. The filtrate was concentrated and separated by column chromatography to obtain the target compound 160-1 (75 mg, 94%).

[1478] Step 160-2: Compound 160-1 was used to obtain the target compound 160 by the same synthesis method as Step 159-4 in Example 159.

[1479] 1H 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).

[1480] MS (ESI, LR) calculated value C 23 H 26 N5O2[M+H] + :404.2, measured value:404.1.

[1481] Example 161. (7-(3-Chlorophenyl)-1H-indazol-3-yl)(piperidin-1-yl)methanone

[1482] <Scheme 49>

[1483]

[1484] The target compound 161 was obtained by the same synthesis method as Example 154 using 7-bromo-1H-indazole-3-carboxylic acid and the corresponding compound.

[1485] 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).

[1486] MS (ESI, LR) calculated value C 19 H 19 ClN3O[M+H] + :340.1, measured value:340.1.

[1487] Example 162. (8-(3-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1488] <Scheme 50>

[1489]

[1490] Step 162-1: Methyl tert-butyl ether (TBME) (200 mL) was placed in a reaction vessel and sodium ethoxide (20% solution, 27.7 mL, 71.8 mmol) was added under a nitrogen atmosphere. After stirring for 15 minutes, the temperature was reduced to 0°C. Ethyl chloroacetate (6.99 mL, 65.28 mmol) and ethyl formate (6.82 mL, 84.8 mmol) were added within 1 hour. After stirring for 30 minutes, the temperature was raised to room temperature and stirred for 18 hours. The temperature was lowered to 5°C to 10°C, water (100 mL) was added, and the mixture was stirred for more than 30 minutes. The reaction solution was acidified with hydrochloric acid (pH 1 to 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 obtain the target compound 162-1 (5.2 g, 5%).

[1491] 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 ethanol (10 mL) and 2 drops of sulfuric acid were added. The reaction solution was stirred at 90 ° C for 21 hours. After the reaction was completed, 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 1N sodium hydroxide aqueous solution and brine, dried over anhydrous magnesium sulfate, filtered and concentrated. The residue was separated by column chromatography to obtain the target compound 162-2 (0.654 g, 84%).

[1492] Step 162-3: Compound 162-2 (3.4 g, 12.8 mmol) was dissolved in tetrahydrofuran (30 mL), followed by the addition of sodium hydroxide (0.768 g, 19.2 mmol) dissolved in water (30 mL) and stirred for 3 hours. After completion of the reaction, the reaction solution was concentrated and acidified with 1N aqueous hydrochloric acid (pH approximately 2). The mixture was extracted with n-butanol (30 mL x 4), 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.

[1493] Step 162-4: Compound 162-3 was used to obtain the target compound 162-4 by the same synthesis method as Step 1-2 in Example 1.

[1494] Step 162-5: Compound 162-4 was used to obtain the target compound 162 by the same synthesis method as Step 1-3 in Example 1.

[1495] 1 H NMR (400MHz, DMSO-d6) δ (ppm): 8.87 (dd, J = 7.0, 1.2 Hz, 1H), 8.29 (t, J = 1.9 Hz, 1H), 8.03 (d, J = 7.5 Hz, 2H), 7.7 3(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).

[1496] MS (ESI, LR) calculated value C 19 H 19 ClN3O[M+H] + :340.1, measured value:340.1.

[1497] Example 163. (8-(4-nitrophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1498]

[1499] The target compound 163 was obtained by the same synthesis method as steps 1-3 in Example 1 using compound 162-4 and 4-nitrophenylboronic acid.

[1500] 1HNMR (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).

[1501] MS (ESI, LR) calculated value C 19 H 19 N4O3[M+H] + :351.1, measured value:351.2.

[1502] Example 164. (8-(4-Aminophenyl)imidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1503]

[1504] Compound 163 was used to obtain the target compound 164 by the same synthesis method as Example 7.

[1505] 1 H NMR (400MHz, DMSO-d6) δ (ppm): 8.72 (dd, J = 6.8, 1.2 Hz, 1H), 7.95 (s, 1H), 7.88 (d, J = 8.5 Hz, 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).

[1506] MS (ESI, LR) calculated value C 19 H 21 N4O[M+H] + :321.2, measured value:321.2.

[1507] Example 165. (8-(3-Chlorophenyl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1508] <Scheme 51>

[1509]

[1510] Using 3-bromo-5-methyl-pyridin-2-amine and the corresponding compound, the target compound 165 was obtained by the synthetic method in Example 162.

[1511] 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).

[1512] MS (ESI, LR) calculated value C 20 H 21 ClN3O[M+H] + :354.1, measured value:354.1.

[1513] Example 166. (8-(2-chloropyridin-4-yl)-6-methylimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1514]

[1515] The target compound 166 was obtained by the same synthesis method as steps 1-3 in Example 1 using compound 165-2 and 3-chlorophenylboronic acid.

[1516] 1 HNMR (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).

[1517] MS (ESI, LR) calculated value C 19 H 20 ClN4O[M+H] + :355.1, measured value:355.1.

[1518] Example 167. (8-(3-Chlorophenyl)-6-fluoroimidazo[1,2-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1519]

[1520] Using 3-bromo-5-fluoro-pyridin-2-amine and the corresponding compound, the target compound 167 was obtained by the synthetic method in Example 162.

[1521] 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).

[1522] MS (ESI, LR) calculated value C 19 H 18 ClFN3O[M+H] + :358.1, measured value:358.1.

[1523] Example 168. (7-(4-Methoxyphenyl)-[1,2,3]triazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1524] <Scheme 52>

[1525]

[1526] Step 168-1: Dissolve 2-bromo-6-methyl-pyridine (3 g, 1.98 mmol) in tetrahydrofuran (100 mL), lower the temperature to -78 ° C, add lithium diisopropylamide (2M solution, 17.44 mL, 34.88 mmol), and stir the mixture for 10 minutes. Add N,N,N',N'-tetramethylethylenediamine (TMEDA) (5.23 mL, 34.88 mmol) and stir the mixture at the same temperature for 1 hour. Slowly add methyl chloroformate (2.7 mL, 34.88 mmol) and raise the temperature to room temperature. After the reaction is complete, add water (100 mL) and extract with ethyl acetate (100 mL×2). Wash the combined organic layers with brine, dry over anhydrous magnesium sulfate, filter and concentrate. Use column chromatography to separate the residue to obtain the target compound 168-1 (1.8 g, 45%).

[1527] Step 165-2: Dissolve compound 168-1 (1.37 g, 5.95 mmol) and 4-acetamidophenylsulfonyl azide (1.57 g, 6.5 mmol) in acetonitrile (20 mL) and stir. Lower the temperature to 0°C, add DBU (0.98 mL, 6.5 mmol), raise the temperature to room temperature, and stir the mixture for 12 hours. After the reaction is complete, add saturated aqueous ammonium chloride (50 mL) and filter through Celite. Extract the filtrate with ethyl acetate (50 mL x 3), wash the combined organic layers with brine, dry over anhydrous magnesium sulfate, filter, and concentrate. After solidification with ethyl acetate / diethyl ether (1:10), filtration, and air drying, the target compound 168-2 (0.95 g, 62%) was obtained. [DBU (1,8-diazabicyclo(5,4,0)undec-7-ene)]

[1528] Step 168-3, Step 168-4, Step 168-5: Compound 162-2 was used to obtain the target compound 168 by the same synthesis method as Step 162-3, Step 162-4 and Step 162-5 in Example 162.

[1529] 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).

[1530] MS (ESI, LR) calculated value C 19 H 21 N4NaO2[M+Na] + :359.2, measured value:359.2.

[1531] Example 169. (7-(3-Chlorophenyl)-1H-indol-3-yl)(piperidin-1-yl)methanone

[1532] <Scheme 53>

[1533]

[1534] 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 the reaction was completed, water was added, filtered, and washed with water. The obtained solid product was dried in air. The obtained solid product was dissolved in 4N sodium hydroxide aqueous solution (10 mL) and stirred at 100 ° C for 2 hours. After the reaction was completed, the temperature was lowered to room temperature, acidified with hydrochloric acid (pH of about 1), filtered, and washed with water. The obtained solid product was dried in air to obtain the target compound 169-1 (0.548 g, 78%) in the form of a hydrochloride salt.

[1535] Step 169-2, Step 169-3: Compound 169-1 was used to obtain the target compound 169 by the same synthesis method as Step 162-4 and Step 162-5 in Example 162.

[1536] 1 H 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).

[1537] MS (ESI, LR) calculated value C 20H 20 ClN2O[M+H] + :339.1, measured value:339.1.

[1538] Example 170. (6-(3-Chlorophenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1539] Example 171. (6-(4-Methoxyphenyl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone

[1540] For Examples 170 and 171, methyl-6-bromopyrazolo[1,5-a]pyridine-3-carboxylate and the corresponding compound were synthesized using the same method as Steps 162-3, 162-4, and 162-5 in Example 162. The structural and spectral data are shown in Table 37 below.

[1541] [Table 37]

[1542]

[1543] Example 172. (6-(Benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1544]

[1545] The target compound 172 was obtained by the same synthesis method as Step 162-4 and Step 162-5 in Example 162 using 6-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylic acid and the corresponding compound.

[1546] 1 HNMR (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. 31(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).

[1547] MS (ESI, LR) calculated value C 20 H20 N3O3[M+H] + :350.2, measured value:350.2.

[1548] Example 173. (5-(Benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1549] <Scheme 54>

[1550]

[1551] Using ethyl 5-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylate and the corresponding compound, the target compound 173 was obtained by the same synthesis method as Step 162-5, Step 162-3 and Step 162-4 in Example 162.

[1552] 1 H 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).

[1553] MS (ESI, LR) calculated value C 20 H 20 N3O3[M+H] + :350.2, measured value:350.2.

[1554] Example 174. (4-(Benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[3,2-c]pyridin-2-yl)(piperidin-1-yl)methanone

[1555]

[1556] Using methyl 4-chloro-1H-pyrrolo[3,2-c]pyridine-2-carboxylate and the corresponding compound, the target compound 174 was obtained by the same synthesis method as Step 162-5, Step 162-3 and Step 162-4 in Example 162.

[1557] 1H 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).

[1558] MS (ESI, LR) calculated value C 20 H 20 N3O3[M+H] + :350.2, measured value:350.2.

[1559] Example 175. (4-(Benzo[d][1,3]dioxol-5-yl)-1H-pyrrolo[2,3-c]pyridin-2-yl)(piperidin-1-yl)methanone

[1560]

[1561] Using ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate and the corresponding compound, the target compound 175 was obtained by the same synthesis method as Step 162-5, Step 162-3 and Step 162-4 in Example 162.

[1562] 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)

[1563] MS (ESI, LR) calculated value C 20 H 20 N3O3[M+H] + :350.2, measured value:350.2.

[1564] Example 176. (4-(Benzo[d][1,3]dioxol-5-yl)pyrrolo[2,1-f][1,2,4]triazin-6-yl)(piperidin-1-yl)methanone

[1565]

[1566] Using ethyl 4-chloropyrrolo[2,1-f][1,2,4]triazine-6-carboxylate and the corresponding compound, the target compound 176 was obtained by the same synthesis method as Step 162-5, Step 162-3 and Step 162-4 in Example 162.

[1567] 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).

[1568] MS (ESI, LR) calculated value C 19 H 19 N4O3[M+H] + :351.1, measured value:351.1.

[1569] Example 177. (4-(Benzo[d][1,3]dioxol-5-yl)-7H-pyrrolo[2,3-d]pyrimidin-6-yl)(piperidin-1-yl)methanone

[1570]

[1571] The target compound 177 was obtained by the same synthesis method as Step 162-4 and Step 162-5 in Example 162 using 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-6-carboxylic acid and the corresponding compound.

[1572] 1 H 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).

[1573] MS (ESI, LR) calculated value C 19 H 19 N4O3[M+H] + :351.1, measured value:351.1.

[1574] Example 178. (5-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1575] Example 179. (5-(4-Methoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1576] Example 180. (5-(4-Chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1577] Example 181. (5-(3,4-Dimethoxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1578] Example 182. (5-(4-Fluorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1579] Example 183. (5-(Furan-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1580] Example 184. Piperidin-1-yl(5-(pyridin-4-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)methanone

[1581] Example 185. (5-(3-Chlorophenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1582] Example 186. (5-(3-Chloro-4-hydroxyphenyl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1583] Example 187. (2-(Benzo[d][1,3]dioxol-5-yl)-5H-pyrrolo[3,2-d]pyrimidin-6-yl)(piperidin-1-yl)methanone

[1584] Example 188. (5-(Benzofuran-3-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1585] Example 189. (5-(Naphthyl-2-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1586] Example 190. (5-(1H-indazol-6-yl)-1H-pyrrolo[3,2-b]pyridin-2-yl)(piperidin-1-yl)methanone

[1587] Example 191. 2-(2-(Piperidine-1-carbonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl)isoindolin-1-one

[1588] For Examples 178, 179, 180, 181, 182, 183, 184, 185, 186, 187, 188, 189, 190, and 191, ethyl 5-bromo-1H-pyrrolo[3,2-b]pyridine-2-carboxylate and the corresponding compound were used to obtain the compounds by the same synthetic method as Steps 162-3, 162-4, and 162-5 of Example 162. The structural and spectral data are shown in Table 38 below.

[1589] [Table 38]

[1590]

[1591]

[1592]

[1593] Example 413. 3-Hydroxy-5-[2-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-6-yl]pyridine-2-carbonitrile

[1594] <Scheme 55>

[1595]

[1596] Step 413-1: Using 6-bromopyrazolo[1,5-a]pyridine-3-carboxylic acid, the target compound 413-1 was obtained by the same synthesis method as Step 1-2 in Example 1.

[1597] Step 413-2: Compound 413-1 was used to obtain the target compound 413 by the same synthesis method as Step 159-3 in Example 159.

[1598] 1H 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).

[1599] MS (ESI, LR) calculated value C 19 H 18 N5O2[M+H] + :348.1, measured value:348.1.

[1600] Experimental Example 1.15 Evaluation of PGDH Inhibitory Activity

[1601] The 15-PGDH inhibitory activity of the embodiment compound is measured as follows. 6.7ng of human 15-PGDH (R&D System#5660-DH) enzyme (10 μL) is added to a black 96-well plate, 60 μL of buffer (50mM Tris-HCl, pH 7.5, 0.01% Tween 20) is added, and 10 μL of 200 μM β-nicotinamide adenine dinucleotide sodium salt (Sigma, Cat#N0632-5G) is added. 10 μL of (10x) compound DMSO solution is added, and the reaction is continued at room temperature for 10 minutes. Then, 10 μL of 200 μM prostaglandin E2 is added, and the value is read at intervals of 30 seconds under ex (λ360nm) / em (λ450nm), for 30 minutes, to obtain the result value V 最大 (millimeter per minute). From the result value V 最大 The slope (i.e., linear range) was defined as 0% inhibition of the enzyme alone and 100% inhibition of the substrate alone, and the % inhibition of the compound at each concentration was converted accordingly using Equation 1 below. Nonlinear regression analysis of the resulting values ​​was performed using Prism to obtain the concentration that exhibited 50% inhibition (IC) from the concentration-response curve of the test compound. 50 ).

[1602] <Equation 1>

[1603]

[1604] The results are shown in Table 39 below. In Table 39, IC 50 Value ≤ 100nM: A, 100nM <IC 50 Value ≤ 1000nM: B, IC 50Values > 1000 nM: C. From these values, it was confirmed that each compound inhibited 15-PGDH activity. Therefore, it was confirmed that the compounds of the present invention are direct 15-PGDH inhibitors.

[1605] Experimental Example 2. Measurement of PGE2 increasing activity in A549 cells

[1606] A549 cells were prepared at a cell density of 1×10 5 cells / mL in F12K medium containing 10% FBS (fetal bovine serum), and 2×10 4 cells / 200 μL were added to each well of a 96-well cell culture plate, and then cultured in an incubator containing 5% CO2 at 37°C for 24 hours. After the culture was completed and all the F12K medium was removed, all the wells were washed once with 100 μL of PBS and treated with 160 μL of serum-free F12K medium. Then, 20 μL of IL-1β diluted 10-fold to a concentration of 1 ng / mL in serum-free F12K medium was added to the wells to be treated with IL-1β, and 20 μL of serum-free F12K medium was added to the wells not to be treated with IL-1β. For the wells to be treated with the compound, 20 μL of the compound dissolved in 100% DMSO was diluted to 10 times the desired compound concentration in serum-free F12K medium so that the final DMSO concentration for treating the cells was 0.1%, and for the wells not to be treated with the compound, 20 μL of DMSO diluted in serum-free F12K medium was added so that the final DMSO concentration for treating the cells was 0.1%. To confirm the increase or decrease in the amount of PGE2 secreted in the supernatant collected after culturing in an incubator containing 5% CO2 at 37°C for 24 hours, PGE2 was quantified using Prostaglandin E2 Parameter (SKGE004B).

[1607] As a result, as shown in Table 39 below, it was confirmed that due to the inhibition of 15-PGDH activity by each compound at a concentration of 1 μM, the amount of PGE2 increased (0 < PGE2 increasing ability < 1.5: +, PGE2 increasing ability ≥ 1.5: ++).

[1608] [Table 39]

[1609]

[1610]

[1611]

[1612]

[1613]

[1614]

[1615]

[1616]

[1617] The above description of the present invention is for illustrative purposes only, and it is apparent to those skilled in the art that various replacements and modifications may be made to the invention disclosed herein without departing from the spirit of the invention or the essential features of the invention. Therefore, it should be understood that the above embodiments are merely for illustration of the present invention and are not intended to limit the scope of the invention in any way. For example, each component described in a single form may also be implemented in a distributed manner, and similarly, components described as distributed may also be implemented in a combined form.

[1618] The scope of the present invention is indicated by the following patent claims. The meaning and scope of the patent claims and all modifications or changes derived from their equivalents are considered to fall within the scope of the present invention.

Claims

1. A heterocyclic compound represented by the following formula 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, wherein: <Formula 1> forming a fused bicyclic ring of rings A and B, 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 It is H, R a-1 Substituted C 1-6 Straight chain or branched alkyl, or C(O)R a-1 , R a-1 It is C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, hydroxyl, R s or R u , and R a-1 Optionally, one or more independent R a-2 replace, R a-2 It is C 1-6 Straight-chain or branched alkyl, halogen, C 1-4 haloalkyl, X1 is optionally b Substituted, where R b is amino or C(O)R s , Y1 is optionally substituted by R 1 Replacement, R 1 It is R f , Y2 is optionally 2 replace, R 2 It is C 1-6 Straight or branched alkyl, halogen, C 5-12 Aryl, R u or R f , and R 2 Optionally, one or more independent R 2-1 replace, R 2-1 It is C 1-4 alkoxy, halogen or hydroxy, Y3 is optionally 3 replace, R 3 It is C 5-7 Aryl, R u or R f , and R 3 Optionally, one or more independent R 3-1 replace, R 3-1 It is C 1-4 alkoxy, halogen, hydroxy or cyano, Y4 optional via R 4 or -LR 4 replace, L is -NH(CH2) m -, -NHC(O)-, -NHSO2- or -S-, m is an integer from 0 to 3, R 4 It is a C with 1 to 2 rings 5-12 Aryl, R u 、R s or R f , and R 4 is optionally substituted with one or more than one independent Q, Q is C 1-6 Straight-chain or branched alkyl, halogen, hydroxyl, C 1-4 Halogenated alkyl, C 1-4 Alkoxy, nitro, cyano, amino, carboxylate, carboxyl, CHR 5 、CH2R 5 NR 5 R 6 、C(O)R 5 、C(O)OR 5 、C(O)NR 5 R 6 、NHC(O)(CH2) p R 5 、NHC(O)CH2OR 5 、NHC(O)CH2NR 5 R 6 、NHCH2CH2R 5 NR 5 C(O)R 6 、R u or R s , p is an integer from 0 to 3, and Q is optionally substituted by one or more independent R 7 replace, R 5 and R 6 Independently H, C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, C 1-4 Alkoxy, amino, sulfonyl, C 5-7 Aryl, arylalkyl, R u or R s , R 7 It is C 1-6 Straight-chain or branched alkyl, C 3-8 Cycloalkyl, halogen, C 1-4 Haloalkyl, hydroxy, C 1-4 Alkoxy, hydroxyalkyl, cyano, amino, alkylamino, C 1-6 Alkyl carboxylate group, nitro group, R u 、 u Substituted C 1-4 Alkyl or R s , and Q and R 7 The bond between them is a single bond or a double bond, R s is a 4- to 10-membered saturated heterocycloalkyl ring having 1 to 2 rings, which has 1 to 3 heteroatoms selected from N, O and S, R u is a 5- to 7-membered unsaturated heterocycloalkyl ring having 1 to 4 heteroatoms selected from N, O and S, R f is a fused bicyclic ring in which a 5- to 7-membered saturated or unsaturated heterocycloalkyl ring having 1 to 2 heteroatoms selected from N, O and S is fused to an aryl ring or a 5- to 7-membered heteroaryl ring having 1 to 2 N, R s 、R u and R f are independently optionally substituted with one to two oxy (O) or sulfydene (S) substituents. 2 . The compound according to claim 1 , a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, wherein Ring A is pyrrole, pyrazole, imidazole, or triazole. 3 . The compound according to claim 1 , a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, wherein the B ring is benzene, pyridine, pyrimidine, or triazine.

4. The compound according to claim 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, wherein the fused bicyclic ring of rings A and B is 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, wherein the fused bicyclic ring of ring A and ring B is one selected from the following:

6. The compound according to claim 1, its hydrate, its solvate or its pharmaceutically acceptable salt, wherein R a is H, propyl, C(O)R a-1 , R a-1 is methyl, butyl, cyclohexyl, hydroxy, piperidinyl, azaspiroheptyl, azaspirooctyl, azaspironanyl, azabicycloheptyl, azabicyclooctyl, azabicyclononanyl or tetrahydropyridinyl, and R a-2 is methyl, ethyl, propyl, isopropyl, fluoro or trifluoromethyl.

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

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

9. The compound according to claim 1, its hydrate, its solvate or its pharmaceutically acceptable salt, wherein R 2 is methyl, fluoro, phenyl, naphthyl (naphthyl), furyl, pyridyl, isoindolinone, benzodioxolyl, dihydrobenzodioxinyl, benzofuranyl or indazolyl, and R 2-1 is methoxy, chlorine, fluorine or hydroxy.

10. The compound according to claim 1, its hydrate, its solvate or its pharmaceutically acceptable salt, wherein R 3 is phenyl, pyridyl or benzodioxolyl, and R 3-1 is methoxy, chloro, hydroxy or cyano.

11. The compound according to claim 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, wherein L is -NH-, -NHCH2-, -NH(CH2)2-, -NHC(O)-, -NHSO2-, or -S-.

12. The compound according to claim 1, its hydrate, its solvate or its pharmaceutically acceptable salt, wherein R 4 is phenyl, naphthyl (naphthyl), furanyl, pyrazolyl, dihydropyridinyl, pyridinyl, pyrimidinyl, pyridone, pyrimidinone, isoxazolyl, piperidinyl, benzodioxolyl, isoindolinone, dihydroisoquinolinone, benzofuranyl, benzothiophenyl, indolyl, indazolyl, quinolinyl, quinolinone, isoquinolinone, dihydropyrrolopyridone, benzisoxazolone, dihydronaphthyridinone, benzoxazolyl, benzisoxazolyl, triazolopyridone, phthalazinone, quinazolinone or pyridopyrimidone.

13. The compound according to claim 1, a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, wherein Q is methyl, propyl, isopropyl, fluorine, chlorine, bromine, hydroxyl, trifluoromethyl, methoxy, nitro, cyano, amino, carboxylate, carboxyl, CHR 5 、CH2R 5 NR 5 R 6 、C(O)R 5 、C(O)OR 5 、C(O)NR 5 R 6 、NHC(O)R 5 、NHC(O)CH2R 5 、NHC(O)(CH2)2R 5 、NHC(O)CH2OR 5 、NHC(O)CH2NR 5 R 6 、NHCH2CH2R 5 NR 5 C(O)R 6 , tetrazolyl, oxadiazolyl, oxadiazolone, furanyl, thienyl, imidazolyl, pyrazolyl, isoxazolyl, thiazolyl, oxy-thiadiazolyl, thio-oxadiazolyl, pyridyl, pyrimidinyl, azetidinyl, oxazolidinone, piperidinyl, piperazinyl, morpholinyl, azaspiroheptanyl, azaspirooctanyl, azaspirononanyl, azabicycloheptanyl or azabicyclooctanyl, R 5 is H, methyl, ethyl, butyl, cyclopropyl, cyclohexyl, methoxy, amino, phenyl, benzyl, imidazolyl, oxadiazolyl, oxadiazolone, pyridinyl, pyrimidinyl, azetidinyl, piperidinyl, piperidone, piperazinyl, morpholinyl, thiazolidinedione, piperazinone, piperazine-dione, azaspiroheptanyl, or azaspirononanyl, and R 6 is H, methyl, ethyl, propyl, isopropyl, sulfonyl, pyrazolyl, pyridinyl, pyridazinyl, azetidinyl or piperidinyl.

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

15. The compound according to claim 1, its hydrate, its solvate or its pharmaceutically acceptable salt, wherein the compound represented by Formula 1 is selected from: [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)cyanopyridine, [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)propionamide, [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)cyclopropylcarboxamide, [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)cyclohexylcarboxamide, [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)propionamide, [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)cyclopropylcarboxamide, [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)cyclohexylcarboxamide, [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-morpholinylpyridin-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) ketone, [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)acrylamide, [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]amino]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-pyridinyl]methanone, [215] (7-(6-(2-azabicyclo[2.2.1]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [216] (7-(6-(2-azabicyclo[2.2.2]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]heptane-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] 1-(5-(3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)pyridin-2-yl)azetidine-3-carboxylic acid methyl ester, [220] (7-(6-(2-azaspiro[3.3]heptane-2-yl)pyridin-3-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [221] (7-(6-(3-(hydroxymethyl)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]heptane-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-pyridinyl]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) ketone, [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-piperidinyl)methanone, [239] 4-chloro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]benzamide, [240] 1,3,5-trimethyl-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyrazole-4-sulfonamide, [241] 5-fluoro-N-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-3-carboxamide, [242][7-[2-(4-chlorophenyl)ethylamino]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone, [243] 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid, [244] 3-fluoro-5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]pyridine-2-carboxylic acid methyl ester, [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-pyridinyl]-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-piperidinyl)methanone, [249] [7-[5-fluoro-6-(morpholine-4-carbonyl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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-piperidinyl)methanone, [260][7-(3-amino-1H-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone, [261][7-(3-amino-1-methyl-indazol-5-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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)pyridine cyanide, [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-piperidinyl)methanone, [277] [7-[2-(azetidine-1-carbonyl)pyrimidin-5-yl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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-piperidinyl)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-piperidinyl)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-piperidinyl)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-piperidinyl)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-piperidinyl)methanone, [303] [7-[3-Fluoro-4-(5-methyl-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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-piperidinyl)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-piperidinyl)methanone, [310] [7-(3-amino-1-methyl-indazol-6-yl)pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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-piperidinyl)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-piperidinyl)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-piperidinyl)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-piperidinyl-[7-[4-(1H-pyrazol-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]methanone, [347] 1-piperidinyl-[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-piperidinyl)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-piperidinyl)methanone, [351] [7-[4-(5-methylthiazol-2-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone, [352] [7-[4-(1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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-dimethylimidazo 1-4-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone, [359] [7-[4-(5-amino-1,2,4-oxadiazol-3-yl)phenyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone, [360] 5-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]-3H-1,3,4-oxadiazol-2-one, [361] 1-piperidinyl-[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-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone, [365] 1-piperidinyl-[7-[6-(2-thioxo-3H-1,3,4-oxadiazol-5-yl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]methanone, [366] (7-(2-(isoxazol-4-yl)-6-morpholinylpyridin-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-morpholinylpyridin-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'-bipyridyl]-6-yl)oxazolidin-2-one, [371] (7-(2-(3,5-dimethylisoxazol-4-yl)-6-morpholinylpyridin-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-pyridinyl]-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'-bipyridyl]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [376] (7-(5'-fluoro-6-morpholinyl-[2,3'-bipyridyl]-4-yl)pyrazolo[1,5-a]pyridin-3-yl)(piperidin-1-yl)methanone, [377] (7-(2-(2-methylpyrimidin-5-yl)-6-morpholinylpyridin-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-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone, [380] [7-[5-fluoro-6-(1,3,4-oxadiazol-2-yl)-3-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)methanone, [381] [7-[6-(3,5-dimethylisoxazol-4-yl)-5-fluoro-3-pyridyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl]-(1-piperidinyl)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-piperidinyl)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-piperidinyl)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-pyridinyl]-2-pyrimidin-5-yl-acetamide, [408] N-[5-[3-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-7-yl]-2-pyridinyl]-2-[6-(trifluoromethyl)-3-pyridinyl]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-pyridinyl]acetamide, [411] 6-(3-(6-fluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, [412] 6-(3-(6,6-difluoro-2-azaspiro[3.3]heptane-2-carbonyl)pyrazolo[1,5-a]pyridin-7-yl)isoindolin-1-one, and [413] 3-Hydroxy-5-[2-(piperidine-1-carbonyl)pyrazolo[1,5-a]pyridin-6-yl]pyridine-2-carbonitrile. 16 . A pharmaceutical composition for preventing or treating a 15-PGDH-related disease, comprising as an active ingredient the heterocyclic compound according to claim 1 , a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof.

17. The pharmaceutical composition according to claim 16, wherein the 15-PGDH-related disease is one or more selected from the following: inflammatory diseases (inflammatory bowel disease (ulcerative colitis, Crohn's disease), chronic obstructive pulmonary disease (COPD), Behcet's disease, acute liver injury, acute kidney injury, acute lung injury, sepsis, exacerbation of asthma and lung disease, peptic ulcer (ulcer caused by NSAID), vasculitis syndrome, non-alcoholic fatty liver disease (NASH), atopic dermatitis, psoriasis, interstitial cystitis, prostatitis syndrome), fibrosis (pulmonary fibrosis (idiopathic pulmonary fibrosis), renal Fibrosis (glomerulosclerosis), 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 (dry eyes, conjunctivitis, keratitis), thrombocytopenia (drug-induced thrombocytopenia, autoimmune thrombocytopenia, idiopathic thrombocytopenia, thrombocytopenia caused by viral infection), myopathy (muscular dystrophy, muscle damage), anemia (plastic anemia, anemia of chronic disease, Fanconi anemia, β- Thalassemia or unexplained anemia), circulatory diseases (heart disease (angina, heart failure, myocardial infarction), kidney disease (chronic kidney disease, renal failure), stroke, pulmonary hypertension, peripheral circulatory disorders), nerve cell death (mental disorders, neurodegenerative diseases, nerve damage), blood cell reduction (immune blood cell reduction, neutropenia, lymphocytopenia), osteoporosis, fractures, leukemia (acute myeloid leukemia (AML), acute lymphoblastic leukemia (ALL), chronic myeloid leukemia (CML)), lymphoma (Hodgkin lymphoma, non-Hodgkin lymphoma), radiation exposure toxicity, Cancers expressing 15-PGDH, 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 (vertigo, 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 according to claim 1 , a hydrate thereof, a solvate thereof, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive.

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