Novel heterocyclic amine derivatives and pharmaceutical compositions containing the same

Abstract

The present invention relates to a novel heterocyclic amine derivative represented by the following chemical formula 1 and a pharmaceutical composition containing the same, wherein the compounds according to the present invention can be usefully used for the prevention or treatment of inflammatory diseases, autoimmune diseases, or cancer. [Case 1] In the above chemical formula 1, the descriptions of Y1, R1, A, R2, k, Y2, L, X, and R3 are as defined in the specification.

Description

[Technical Field]

[0001] This invention relates to novel heterocyclic amines useful as BTK (Bruton's Tyrosine Kinase) and ITK (Interleukin-2 Tyrosine Kinase) inhibitors, and pharmaceutical compositions containing the same. [Background technology]

[0002] BTK (Bruton's Tyrosine Kinase) and ITK (Interleukin-2 Tyrosine Kinase) are types of TEC (tyrosine kinase expressed in hepatocellular carcinoma) kinases that act on a variety of immune responses.

[0003] BTK functions as a regulator of not only the development of early B-cells but also the activation, signaling, and survival of mature B-cells. These B-cells are activated as mature antibody-producing cells when signals are transmitted by B-cell receptors (BCRs), which recognize antigens attached to the surface of antigen-presenting cells. However, abnormal signaling by BCRs can lead to abnormal B-cell proliferation and the formation of pathological autoantibodies, potentially inducing cancer, autoimmune, and / or inflammatory diseases. Therefore, in abnormal B-cell proliferation, BTK deficiency can block BCR-mediated signaling. Thus, BTK inhibition can block B-cell-mediated disease processes, and the use of BTK inhibitors may be a useful approach for treating B-cell-mediated diseases.

[0004] Furthermore, BTK can be expressed not only by B- cells but also by other cells that may be associated with disease. For example, BTK is an important component of Fc-gamma signaling in microglia cells. Specifically, BTK is known to be useful in regulating diseases such as multiple sclerosis by regulating B- cells and microglia (J Kramer et al. Nature Reviews Neurology. 2023). In addition, mononuclear cells from XLA patients lacking BTK activity show reduced TNF-alpha production after stimulation, and it is known that TNF-alpha-mediated inflammation can be suppressed by BTK inhibitors (see Horwood et al. J.Exp.Med. 197:1603, 2003).

[0005] ITK is known to be an important component of TCR signaling in T cells. T cells are activated by TCR signaling, and activated T cells are associated with autoimmune diseases by generating inflammatory cytokines and activating B cells and macrophages (Sahu N. et al. Curr Top Med Chem. 2009, 9, 690). More recently, it has been reported that ITK- / - mice regulate the development of Th17 and Treg cells, confirming its potential as a therapeutic target for autoimmune diseases (Gomez-Rodriguez J. et al. J. Exp. Med. 2014, 211, 529). More recently, the expression of Th1 and Th17-related cytokines has been confirmed in autoimmune diseases such as multiple sclerosis, and it has been confirmed that Th17-related cytokines IL-17 and IL-23 play an essential role in the pathogenesis of the disease (Shi-Rong Wen. et al. J. Neuroimmunol. 2012. 244, 94-96).

[0006] As a result, substances that inhibit BTK and ITK have been developed, respectively. Specifically, as BTK inhibitors, 4-aminopyrazolo[3,4-d]pyrimidinylpiperidine derivatives were disclosed in WO2008 / 039218, heterocompounds such as pyridine, pyrimidine, pyrazine, and pyridazine compounds were disclosed in WO2015 / 061247, and pyrimidinylphenylacrylamide derivatives were disclosed in WO2014 / 055934. Furthermore, as ITK inhibitors, aminobenzimidazole derivatives were disclosed in WO2005 / 066335, pyridone derivatives were disclosed in WO2005 / 056785, aminothiazole derivatives were disclosed in WO2002 / 050071, and benzimidazole derivatives were disclosed in WO2014 / 036016.

[0007] On the other hand, autoimmune diseases such as multiple sclerosis are caused by a combination of B-cell and T-cell-related factors (Kathrine E. Attfield et al. Nature Reviews Immunology. 2022. 734-750), so suppressing B-cells and T-cells simultaneously may be more effective in treating the disease than suppressing each of them individually.

[0008] However, because BTK acts on B cells as a kinase expressed below the B cell receptor, and ITK acts on T cells as a kinase expressed below the T cell receptor, BTK and ITK target different substances. Therefore, it is difficult to predict the ITK inhibitory effect of a BTK inhibitor, and developing a substance that dually inhibits both BTK and ITK has not been easy.

[0009] Therefore, the inventors, after studying novel compounds, confirmed that compounds having a different chemical structure from BTK and ITK inhibitors reported to date possess excellent dual activity inhibitory effects against BTK and ITK, thus completing the present invention. While the compounds belonging to the present invention mainly possess BTK and ITK inhibitory activity themselves, the possibility that after being absorbed into the body, they may exhibit pharmacological effects as efficacy agents due to special internal environments or metabolic products is not ruled out.

Summary of the Invention

Problems to be Solved by the Invention

[0010] The present invention provides a novel heterocyclic amine derivative useful as a BTK and / or ITK inhibitor and a pharmaceutical composition containing the same.

Means for Solving the Problems

[0011] In order to solve the above problems, the present invention provides a compound represented by the following Chemical Formula 1, or a pharmaceutically acceptable salt thereof.

Chemical Formula

[0012] Preferably, Y1 may be a single bond, methylene, or ethylene.

[0013] Preferably, R1 is unsubstituted or a halogen, cyano, hydroxy, or C 1-4 Alkyl and C 1-4It may be substituted with one to three substituents selected from the group consisting of haloalkyl groups.

[0014] More preferably, R1 is unsubstituted or may be substituted with one to three substituents selected from the group consisting of chloro, fluoro, cyano, hydroxy, methyl, monofluoromethyl, difluoromethyl, and trifluoromethyl.

[0015] For example, R1 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, n-heptyl, isoheptyl, n-oxyl, isooxyl, n-nonyl, isononyl, n-decyl, isodecyl, methoxy, ethoxy, propoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, phenyl, biphenylyl, terphenylyl, naphthyl, pyridinyl, pyrimidinyl, tetrahydrofuranil, or tetrahydropyranil. Here, R1 is either unsubstituted or a halogen, cyano, hydroxy, or C. 1-4 Alkyl and C 1-4 It may be substituted with one to three substituents selected from the group consisting of haloalkyl groups.

[0016] For example, R1 is methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, methoxy, ethoxy, propoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyridinyl, tetrahydrofuranyl, or tetrahydropyranyl. Here, R1 may be unsubstituted or substituted with one to three substituents selected from the group consisting of chloro, fluoro, cyano, hydroxy, methyl, monofluoromethyl, difluoromethyl, and trifluoromethyl.

[0017] Furthermore, preferably, if Y1 is a single bond, R1 is C 1-10 Alkyl, or C 3-10 It is a cycloalkyl, Here, R1 is either unsubstituted or a halogen, cyano, hydroxy, or C. 1-4 Alkyl and C 1-4 It may be substituted with one or more substituents selected from the group consisting of haloalkyl groups.

[0018] For example, if Y1 is a single bond, then R1 can be methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Here, R1 may be unsubstituted or substituted with one to three substituents selected from the group consisting of chloro, fluoro, cyano, hydroxy, methyl, monofluoromethyl, difluoromethyl, and trifluoromethyl.

[0019] Furthermore, preferably, Y1 is C 1-4 Alkylene or C 1-4 In the case of haloalkylenes, R1 is C 1-10 Alkoxy, C 3-10 Cycloalkyl, C 6-20 The aryl, N-containing 6-membered heteroaryl, tetrahydrofuranil, or tetrahydropyranil are available. Here, R1 is either unsubstituted or a halogen, cyano, hydroxy, or C. 1-4 Alkyl and C 1-4 It may be substituted with one or more substituents selected from the group consisting of haloalkyl groups.

[0020] For example, Y1 is C 1-4 Alkylene or C 1-4In the case of haloalkylenes, specifically, for example, if Y1 is methylene or ethylene, then R1 is methoxy, ethoxy, propoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyridinyl, tetrahydrofuranyl, or tetrahydropyranyl. Here, R1 may be unsubstituted or substituted with one to three substituents selected from the group consisting of chloro, fluoro, cyano, hydroxy, methyl, monofluoromethyl, difluoromethyl, and trifluoromethyl.

[0021] Preferably, A may be benzene, thiazole, thiadiazole, imidazole, pyrazole, pyrazine, pyridine, pyrimidine, or a pyridine-2(1H)-one ring.

[0022] more, [ka] It may be represented by any one of the following chemical formulas A1 to A12. [ka] In chemical formulas A1 to A12, R2 is defined as shown in Chemical Formula 1.

[0023] Preferably, R2 may be independently hydrogen, chloro, fluoro, cyano, methyl, ethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxy, or -CONH(methyl).

[0024] On the other hand, k represents the number of R2s, and if k is 2, the two R2s may be identical or different.

[0025] more, A is benzene, thiazole, thiadiazole, pyrazine, pyridine, or pyridine-2(1H)-one ring, and R2 is independently a halogen, cyano, or C 1-4Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy, C 1-4 It is a haloalkoxy or -CONH (methyl); A is an imidazole ring and R2 is hydrogen, or A is a pyrazole or pyrimidine ring, and R2 is independently hydrogen, halogen, or C. 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy, or C 1-4 A haloalkoxy may also be used.

[0026] Preferably, Y2 may be a single bond, -O-, or -O-(methylene).

[0027] In this case, if Y2 is -O-(methylene), the (methylene) may be connected to L.

[0028] Preferably, if Y2 is a single bond, L may be any one of the linking groups represented by chemical formulas 2a to 2g.

[0029] For example, if Y2 is a single bond, L may be any one of the linking groups represented by chemical formulas 2a, 2b, 2c, 2e, 2f, and 2g.

[0030] Furthermore, preferably, Y2 is -O- or -O-(C 1-4 In the case of alkylenes, L may be any one of the linking groups represented by the chemical formulas 2h to 2k.

[0031] For example, if Y2 is -O-, then L may be a linking group represented by chemical formula 2i or 2k.

[0032] Also, for example, Y2 is -O-(C 1-4 In the case of alkylenes, L may be a linking group represented by the chemical formula 2h or 2i.

[0033] On the other hand, a represents the number of Zs, and if a is 2, the two Zs may be identical or different.

[0034] Preferably, L may be any one of the linking groups represented by chemical formulas 2a, 2b, 2c, 2e, 2f, 2g, 2h, 2i, and 2k.

[0035] For example, in chemical formula 2a, n may be 2 and a may be 0.

[0036] Furthermore, for example, in chemical formula 2b, n may be 1 or 2, and a may be 0 or 1.

[0037] Furthermore, for example, in chemical formula 2c, L' may be methylene-O-methylene and a may be 0.

[0038] Furthermore, for example, in chemical formula 2e, v and w may each be 1, and a may be 0.

[0039] Furthermore, for example, in chemical formula 2f, v and w may each be 1; or v may be 1, w 2, and a 0.

[0040] Furthermore, for example, in 2g of the chemical formula, a may be 0, 1, or 2.

[0041] Furthermore, for example, in the chemical formula 2h, n may be 0, 1, or 2, and a may be 0, 1, or 2.

[0042] Furthermore, for example, in chemical formula 2i, n may be 0, 1, or 2, and a may be 0, 1, or 2.

[0043] Furthermore, for example, in chemical formula 2k, p and q may each be independently 1 or 2, r may be 0 or 1, and s may be 2, 3, or 4.

[0044] In this case, p+q is 2 or 3, and r+s may be 2, 3, or 4.

[0045] Furthermore, preferably, L may be any one linking group selected from the group represented below. [ka] In, Z and a are defined as in Chemical Formula 1, * indicates the point where Y2 in chemical formula 1 is connected.

[0046] Preferably, **-Y2-L- may be any one of the linking groups represented by the following chemical formulas 3a to 3r. [ka] In chemical formulas 3a to 3r, m is either 0 or 1. Z and a are defined as in Chemical Formula 1, ** represents the point where the fourth carbon is attached to the pyrrolo[3,2-c]pyridine ring in chemical formula 1.

[0047] Furthermore, for example, if Y2 is -O-, the compound may be a stereoisomer represented by the following chemical formula 1A or 1B, or a mixture thereof. [ka] In chemical formulas 1A and 1B, Y1, R1, A, R2, k, L, X, and R3 are defined as shown in Chemical Formula 1.

[0048] Furthermore, for example, if Y2 is -O- (methylene), the compound may be a stereoisomer represented by the following chemical formulas 1C or 1D, or a mixture thereof. [ka] In chemical formulas 1C and 1D, Y1, R1, A, R2, k, L, X, and R3 are defined as shown in Chemical Formula 1.

[0049] Preferably, Z may be chloro, fluoro, methyl, or methoxy.

[0050] Preferably, R3 is unsubstituted or may be substituted with one or two substituents selected from the group consisting of chloro, fluoro, NH2, NH(methyl), and N(methyl)2.

[0051] More preferably, R3 is -CH3, -CH=CH2, -CH=CHCH3, -C≡CH, or -C≡CCH3. Here, R3 may be unsubstituted or substituted with one or two substituents selected from the group consisting of chloro, fluoro, NH2, NH(methyl), and N(methyl)2.

[0052] For example, R3 may be -CH3, -CH2Cl, -CH=CH2, -CF=CH2, -CH=CHCH3, -CH=CHCH2N(CH3)2, -C≡CH, or -C≡CCH3.

[0053] On the other hand, the compound represented by chemical formula 1 may also be represented by any one of the following chemical formulas 1-1 to 1-3. [ka] In chemical formulas 1-1 to 1-3, R'2 is halogen, cyanoacrylate, C 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy, C 1-4 Haloalkoxy, or -CONH(C 1-4 It is alkyl, Y1, R1, A, R2, Y2, L, and R3 are defined as shown in Chemical Formula 1.

[0054] For example, R'2 may be chloro, fluoro, cyano, methyl, ethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxy, or -CONH(methyl).

[0055] Preferably, in chemical formula 1-1, A is a thiazole, thiadiazole, imidazole, pyrazole, pyrazine, pyridine, pyrimidine, or pyridine-2(1H)-one ring. L may be any one of the linking groups represented by chemical formulas 2a, 2b, 2c, 2e, 2f, 2g, 2h, 2i, and 2k.

[0056] Preferably, in chemical formula 1-2, A is a benzene ring, L may be a linking group represented by the chemical formula 2i.

[0057] Preferably, in chemical formulas 1-3, A is a thiazole ring, L may be a linking group represented by the chemical formula 2i.

[0058] Preferably, A is of chemical formula A1, R2 is halogen, cyanoacrylate, C 1-4 Alkyl, C 1-4 Haloalkyl, or -CONH(C 1-4 It is alkyl, Y2 is a single bond, -O-, or -O-(C 1-4 Alkilen) L may be any one of the linking groups represented by chemical formulas 2a-2c and 2e-2k.

[0059] Preferably, A is of chemical formula A2, R2 is C 1-4 Alkyl or C 1-4 It is a haloalkyl, Y2 is a single bond, L may be a linking group represented by chemical formula 2b.

[0060] Preferably, A is of chemical formula A3, R2 is hydrogen, Y2 is a single bond, L may be a linking group represented by chemical formula 2b.

[0061] Preferably, A is chemical formula A4, R2 is C 1-4 Alkyl or C 1-4 It is a haloalkyl, Y2 is a single bond, L may be a linking group represented by chemical formula 2b.

[0062] Preferably, A is chemical formula A5 or A6. R2 is hydrogen, halogen, C 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy, or C 1-4 It is a haloalkoxy, Y2 is -O-, L may be a linking group represented by the chemical formula 2i.

[0063] Preferably, A is of chemical formula A7, R2 is halogen, C 1-4 Alkyl or C 1-4 It is a haloalkyl, Y2 is a single bond, L may be a linking group represented by chemical formula 2b.

[0064] Preferably, A is of chemical formula A8, R2 is hydrogen, halogen, C 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy, or C 1-4 It is a haloalkoxy, Y2 is a single bond or -O-, L may be a linking group represented by chemical formula 2b or 2i.

[0065] Preferably, A is of chemical formula A9, R2 is hydrogen, halogen, C 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy, or C 1-4 It is a haloalkoxy, Y2 is -O-, L may be a linking group represented by the chemical formula 2i.

[0066] Preferably, A is of chemical formula A10, R2 is C 1-4 Alkoxy or C 1-4 It is a haloalkoxy, Y2 is -O-, L may be a linking group represented by the chemical formula 2i.

[0067] Preferably, A is of chemical formula A11. R2 is C 1-4 Alkyl or C 1-4 It is a haloalkyl, Y2 is -O-, L may be a linking group represented by the chemical formula 2i.

[0068] Preferably, A is of chemical formula A12. R2 is independent of halogen and C 1-4 Alkyl, or C 1-4 It is a haloalkyl, Y2 is -O-, L may be a linking group represented by the chemical formula 2i.

[0069] On the other hand, typical examples of compounds represented by chemical formula 1 are as follows: 1) 1-(4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 2) 1-(4-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 3) 1-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2,5-dihydro-1H-pyrrole-1-yl)prop-2-en-1-one, 4) 1-(4-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 5)1-(4-(1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 6) 1-(4-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 7) 1-(4-(1-(cyclobutylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 8) 1-(4-(6-((5-methylthiazole-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 9) 1-(4-(1-(cyclohexylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 10) 1-(4-(1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 11) 1-(4-(1-((4,4-difluorocyclohexyl)methyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 12) 1-(4-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 13)(S)-1-(4-(1-(sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 14)(R)-1-(4-(1-(sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 15) 1-(4-(1-benzyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 16)1-(4-(6-((5-methylthiazole-2-yl)amino)-1-phenethyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 17) 1-(4-(6-((5-methylthiazole-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 18) 1-(4-(1-(3,3-dimethylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 19) 1-(4-(6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 20)1-(4-(1-(2,2-difluorocyclopropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 21) 1-(4-(1-(difluoromethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 22)2-(4-(1-acryloyl-1,2,3,6-tetrahydropyridine-4-yl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-1-yl)-2-methylpropanenitrile, 23)2-(4-(1-acryloyl-1,2,5,6-tetrahydropyridine-3-yl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-1-yl)-2-methylpropanenitrile, 24)(R)-1-(4-(6-((5-methylthiazole-2-yl)amino)-1-(1,1,1-trifluoropropan-2-yl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 25) 1-(4-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3-methyl-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 26) 1-(4-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2,3,6,7-tetrahydro-1H-azepine-1-yl)prop-2-en-1-one, 27) 1-(7-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3-oxa-9-azabicyclo[3.3.1]non-6-en-9-yl)prop-2-en-1-one, 28) 1-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 29) 1-(3-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 30)1-(3-(6-((5-methylthiazole-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 31) 1-(3-(1-(2,2-difluorocyclopropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 32) 1-(3-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 33) 1-(3-(1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 34) 1-(3-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 35) 1-(3-(6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 36) 1-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-9-azabicyclo[3.3.1]non-2-en-9-yl)prop-2-en-1-one, 37) 1-(3-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-9-azabicyclo[3.3.1]non-2-en-9-yl)prop-2-en-1-one, 38) 1-(3-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-9-azabicyclo[3.3.1]non-2-en-9-yl)prop-2-en-1-one, 39) 1-(3-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 40)1-(4-(6-((1H-imidazole-2-yl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 41) 1-(4-(1-isopropyl-6-((5-methyl-1,3,4-thiadiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 42) 1-(4-(1-isopropyl-6-((4-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 43) 1-(4-(1-isopropyl-6-(pyrimidine-4-ylamino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 44) 1-(4-(1-isopropyl-6-((6-methylpyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 45) 1-(4-(1-isopropyl-6-((6-(trifluoromethyl)pyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 46) 1-(4-(1-isopropyl-6-((6-methoxypyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 47) 1-(4-(6-((4-fluoropyridine-2-yl)amino)-1-isopropyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 48) 1-(4-(1-isopropyl-6-((4-(trifluoromethyl)pyridine-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 49) 1-(4-(1-isopropyl-6-((4-methylpyridine-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 50)N-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 51) N-(2-fluoro-3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 52)N-(2-methoxy-3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 53) N-(3-methyl-5-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 54) N-(2-fluoro-5-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 55) N-(2-methyl-5-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 56) N-(2,6-dimethyl-3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 57) N-(2,6-difluoro-3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 58) N-(3-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-methylphenyl)acrylamide, 59) N-(4-fluoro-3-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 60)N-(2,4-difluoro-5-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 61) N-(3-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-4-fluorophenyl)acrylamide, 62) N-(3-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-methylphenyl)acrylamide, 63) N-(4-fluoro-3-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 64) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-fluorophenyl)acrylamide, 65) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-methylphenyl)acrylamide, 66) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2,4-difluorophenyl)acrylamide, 67) N-(2,4-difluoro-5-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 68)(S)-N-(3-(1-(sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-4-fluorophenyl)acrylamide, 69) N-(5-(1-(3,3-dimethylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2,4-difluorophenyl)acrylamide, 70)N-(3-(1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-4-fluorophenyl)acrylamide, 71) N-(4-fluoro-3-(6-((5-methylthiazole-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 72) N-(2-fluoro-5-(6-((5-methylthiazole-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 73) N-(2-fluoro-3-(6-((5-methylthiazole-2-yl)amino)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 74) N-(5-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-methylphenyl)acrylamide, 75) N-(3-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-4-fluorophenyl)acrylamide, 76) N-(5-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-fluorophenyl)acrylamide, 77) N-(2,4-difluoro-5-(6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 78) N-(4-fluoro-3-(6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 79)(S)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 80)1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 81)(S)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 82)(R)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 83)1-((3S,4R)-3-fluoro-4-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 84)(S)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 85)(S)-1-(2-(((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 86)(S)-1-(2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 87)1-((2R,4S)-4-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 88)1-((2S,4S)-4-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 89)(R)-1-(2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 90)(R)-1-(2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 91)1-((3R,4R)-3-fluoro-4-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 92)Rac-1-((3S,4R)-3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-methylpyrrolidine-1-yl)prop-2-en-1-one, 93)(R)-1-(4,4-difluoro-2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 94)1-((2R,4S)-2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)-4-methoxypyrrolidine-1-yl)prop-2-en-1-one, 95)(S)-1-(3-((1-isopropyl-6-((6-(trifluoromethyl)pyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 96)1-((2R,4S)-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 97)(S)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 98)1-((2R,4S)-4-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 99)(S)-1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 100)1-((2R,4S)-4-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 101)(S)-1-(3-((1-isopropyl-6-((6-methylpyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 102)(S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 103)(S)-1-(3-((1-isopropyl-6-((6-methoxypyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 104)(S)-1-(3-((1-isobutyl-6-((6-methylpyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 105)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 106)1-((3R,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 107)1-((3R,4S)-3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 108)1-((3R,4R)-3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 109)1-((3R,4S)-3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 110)1-((3R,4R)-3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 111)1-((S)-3-((1-((S)-sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 112)1-((3R,4S)-3-((1-((S)-sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 113)1-((3R,4R)-3-((1-((S)-sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrroridine-1-yl)prop-2-en-1-one, 114)(S)-1-(3-((1-isopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 115)1-((3R,4R)-3-fluoro-4-((1-isopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 116)1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-methylpyrrolidine-1-yl)prop-2-en-1-one, 117)(S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-(pyridine-2-ylmethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrroridine-1-yl)prop-2-en-1-one, 118)1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 119)1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 120)1-((3R,4R)-3-fluoro-4-((6-((5-methylthiazole-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 121)(S)-1-(3-((1-benzyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 122)(S)-1-(3-((6-((5-ethylthiazole-2-yl)amino)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 123)1-((3S)-3-((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrroridine-1-yl)prop-2-en-1-one, 124)(S)-1-(3-((1-butyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 125)(S)-1-(3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 126)(S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 127)(S)-1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 128)(S)-1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 129)(S)-1-(3-((1-(cyclohexylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 130)(S)-1-(3-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 131)1-((3S,4R)-3-fluoro-4-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 132)1-((3R,4S)-3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 133)(S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 134)1-((3S,4S)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 135)1-((3R,4S)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 136)1-(6-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-1-azaspiro[3,3]heptan-1-yl)prop-2-en-1-one, 137)1-(6-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-1-azaspiro[3,3]heptan-1-yl)prop-2-en-1-one, 138)(S)-1-(3-((6-((5-fluoro-2-methylphenyl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 139)1-((3S,4R)-3-fluoro-4-((6-((5-fluoro-2-methylphenyl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 140)(S)-1-(3-((1-(2-hydroxy-2-methylpropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 141)1-((3S,4R)-3-fluoro-4-((1-(2-hydroxy-2-methylpropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 142)1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 143)(R)-1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 144)(R)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrroridine-1-yl)prop-2-en-1-one, 145)1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 146)1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 147)1-((3S,4R)-3-fluoro-4-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 148)(S)-1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 149)(S)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 150)(S)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 151)(S)-1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 152)1-((3R,4S)-3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 153)(S)-1-(3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 154)1-((3R,4R)-3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 155)1-(3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 156)(R)-1-(3-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 157)1-((3R,4R)-3-fluoro-4-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 158)(S)-1-(3-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 159)1-((3S,4R)-3-fluoro-4-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 160)(S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 161)1-((3R,4R)-3-fluoro-4-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 162)(R)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 163)1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 164)1-((2S,4S)-4-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 165)1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 166)1-(3-methyl-3-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 167)1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 168)1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 169)(S)-1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 170)1-((3R,4R)-3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 171)1-((3S,4R)-3-fluoro-4-((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 172)1-((3S)-3-((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 173)1-((3R,4R)-3-fluoro-4-((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 174)1-((3R,4R)-3-fluoro-4-((1-((R)-2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 175)1-((3R,4R)-3-fluoro-4-((1-((S)-2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 176) 1-(3-methyl-3-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 177)1-(3-((1-isopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 178)1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 179)1-((2S,4S)-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 180)1-((2S,4S)-4-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 181)2-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-6-yl)amino)thiazole-5-carbonitrile, 182)2-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-6-yl)amino)-N-methylthiazole-5-carboxamide, 183)(S)-1-(3-((1-isopropyl-6-((4-methoxypyrimidine-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 184)(S)-1-(3-((1-isopropyl-6-((3-methoxypyrazine-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 185)1-((2S,4S)-2-methyl-4-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 186)1-((2S,4S)-4-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 187)1-((2S,4S)-2-methyl-4-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 188)(S)-1-(3-((1-(2-fluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 189)1-((3S,4R)-3-fluoro-4-((1-(2-fluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 190)(S)-1-(3-((1-(3-fluoropropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 191)1-((3S,4R)-3-fluoro-4-((1-(3-fluoropropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 192)(S)-1-(3-((6-((1H-pyrazole-3-yl)amino)-1-isopropyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 193)(S)-1-(3-((1-isopropyl-6-((1-methyl-1H-pyrazole-3-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 194)(S)-1-(3-((1-isopropyl-6-((5-methyl-1H-pyrazole-3-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 195)1-((3R,4S)-3-((6-((1H-pyrazole-3-yl)amino)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 196)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methyl-1H-pyrazole-3-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 197)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((1-methyl-1H-pyrazole-3-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 198)(S)-3-((4-((1-acryloylpyrrolidine-3-yl)oxy)-1-isopropyl-1H-pyrrolol[3,2-c]pyridine-6-yl)amino)-1-methylpyridine-2(1H)-1-one, 199)3-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-6-yl)amino)-1-methylpyridine-2(1H)-one, 200)1-(2-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-5-azaspiro[3,4]octan-5-yl)prop-2-en-1-one, 201)1-(7-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-1-azaspiro[4,4]nonan-1-yl)prop-2-en-1-one, 202)1-(2-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-6-azaspiro[3,4]octan-6-yl)prop-2-en-1-one, 203)1-(2-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-5-azaspiro[3.5]nonan-5-yl)prop-2-en-1-one, 204)1-(7-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-azaspiro[4,4]nonan-2-yl)prop-2-en-1-one, 205)(S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 206)(S)-1-(3-((1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 207)(R)-1-(2-(((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 208)(R)-1-(2-(((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 209)(R)-1-(2-(((1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 210)(R)-1-(2-(((1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 211)1-((3S,4R)-3-fluoro-4-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 212)1-((2R,4S)-2-methyl-4-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 213)1-((S)-3-((6-((5-methylthiazole-2-yl)amino)-1-((R)-1,1,1-trifluoropropan-2-yl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 214)(R)-1-(3-(((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)piperidine-1-yl)prop-2-en-1-one, 215)(S)-1-(3-(((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)piperidine-1-yl)prop-2-en-1-one, 216)(S)-1-(3-(((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 217)1-(2-(((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 218)1-(2-(((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 219)(S)-1-(2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 220)(S)-1-(2-(((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 221)1-((2S)-2-(((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 222)(S)-1-(2-(((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 223)(R)-1-(2-(((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 224)(S)-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 225)(S)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-in-1-one, 226)(S,E)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)buto-2-en-1-one, 227)(S,E)-4-(dimethylamino)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)buto-2-en-1-one, 228)N-(4-(((3R,4S)-4-fluoro-1-(vinylsulfonyl)pyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolol[3,2-c]pyridine-6-yl)-5-methylthiazole-2-amine, 229) 2-Chloro-1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)ethane-1-one, 230)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)buto-2-in-1-one, and 231)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-in-1-one.

[0070] On the other hand, compounds represented by chemical formula 1 can be understood as a concept that encompasses stereoisomers, mixtures of stereoisomers, and isotopic derivatives of the compound.

[0071] Specifically, a "stereoisomer" of a compound can be understood as encompassing all possible diastereomers and enantiomers of the compound's structure, provided the compound contains one or more chiral centers.

[0072] Furthermore, "isotopic derivatives" of a compound refer to compounds in which one or more atoms in the compound are replaced by their spontaneously occurring or unspontaneously occurring isotopes. For example, isotopic derivatives of a compound include compounds in which at least one hydrogen atom in the compound is replaced by deuterium.

[0073] Furthermore, the compounds of the present invention may exist in the form of salts, particularly pharmaceutically acceptable salts. Any salt commonly used in the industry may be used without limitation, such as an acid addition salt formed by a pharmaceutically acceptable free acid. In the present invention, "pharmaceutically acceptable salt" means any organic or inorganic addition salt of a compound at a concentration that is relatively non-toxic and harmless to the patient and whose side effects do not diminish the beneficial efficacy of the compound represented by chemical formula 1.

[0074] As free acids, organic acids and inorganic acids can be used. As inorganic acids, hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, stannic acid, etc., can be used. As organic acids, methanesulfonic acid, p-toluenesulfonic acid, acetic acid, trifluoroacetic acid, maleic acid, succinic acid, oxalic acid, benzoic acid, tartaric acid, fumaric acid, mandelic acid, propionic acid, citric acid, lactic acid, glycolic acid, gluconic acid, galacturonic acid, glutamic acid, glutaric acid, glucuronic acid, aspartic acid, ascorbic acid, carboxylic acid, vanillic acid, hydroiodic acid, etc., can be used, but are not limited to these. Preferably, the salt may be a hydrochloride salt.

[0075] Furthermore, pharmaceutically acceptable metal salts can be obtained using a base in a conventional manner. For example, a compound represented by chemical formula 1 can be dissolved in an excess alkali metal hydroxide or alkaline earth metal hydroxide solution, the insoluble compound salt can be filtered out, and the filtrate can be evaporated and dried to obtain a pharmaceutically acceptable metal salt. In this case, it is particularly preferable to produce a sodium salt, a potassium salt, or a calcium salt as the metal salt.

[0076] In addition, salts or solvates of compounds represented by chemical formula 1 that are not pharmaceutically acceptable can be used as intermediates in the manufacture of compounds represented by chemical formula 1, their pharmaceutically acceptable salts, or solvates.

[0077] Furthermore, the compound represented by chemical formula 1 according to the present invention includes not only its pharmaceutically acceptable salt, but also solvates such as hydrates that can be produced therefrom, or prodrugs thereof, without limitation.

[0078] The solvate of the compound represented by chemical formula 1 can be prepared from the compound represented by chemical formula 1 using methods known in the art.

[0079] Furthermore, unless otherwise indicated, the term "prodrug" of a compound can be understood to refer to all derivatives that, under biological conditions (in vitro or in vivo), can be hydrolyzed, oxidized, or otherwise reacted to provide the compound of the present invention, its stereoisomers, mixtures of its stereoisomers, its isotopic derivatives, or pharmaceutically acceptable salts thereof.

[0080] Furthermore, the present invention may include not only the stoichiometric hydrate of the compound represented by chemical formula 1, but also compounds containing various amounts of water. The solvates of the compound represented by chemical formula 1 according to the present invention include all stoichiometric and non-stoichiometric solvates.

[0081] Furthermore, the compound represented by chemical formula 1 can be produced by the following reaction formula 1, for example, when L is one of the linking groups represented by chemical formulas 2a to 2f.

[0082] [ka] In reaction equation 1, P1 represents a protecting group, and the remaining substituents are as defined in chemical formula 1.

[0083] For example, P1 may be any one protecting group selected from the group consisting of tart-butyloxycarbonyl (Boc), carbobenzyloxy (Cbz), para-methoxybenzylcarbonyl (Moz), 9-fluorenylmethyloxycarbonyl (Fmoc), acetyl (Ac), benzoyl (Bz), benzyl (Bn), and para-methoxybenzyl (PMB).

[0084] Step 1-1 is a step in which a compound represented by chemical formula 1-1 and a compound represented by chemical formula 1-2 are reacted to produce a compound represented by chemical formula 1-3. The reaction is a Suzuki-coupling reaction, preferably carried out in the presence of a palladium catalyst and a base.

[0085] Step 1-2 is a step in which a compound represented by chemical formula 1-3 and a compound represented by chemical formula 1-4 are reacted to produce a compound represented by chemical formula 1-5. The reaction is an amine substitution reaction and is preferably carried out in the presence of a palladium catalyst and a base.

[0086] Step 1-3 is a step in which a protecting group is removed from the compound represented by chemical formula 1-5, and then the compound represented by chemical formula 1-6 or 1-7 is reacted to produce the compound represented by chemical formula 1. The removal of the protecting group is preferably carried out under conditions of an acid capable of removing the protecting group, such as trifluoroacetic acid (TFA), and the reaction with the compound represented by chemical formula 1-6 or 1-7 is an amidation reaction, preferably carried out in the presence of a base.

[0087] Furthermore, the compound represented by chemical formula 1 can be produced, for example, by the following reaction equation 2, when L is a linking group represented by chemical formula 2g.

[0088] [ka] In reaction formula 2, P1 represents a protecting group, as defined in reaction formula 1, and the remaining substituents are as defined in chemical formula 1.

[0089] Step 2-1 is a step in which a compound represented by chemical formula 1-1 and a compound represented by chemical formula 1-8 are reacted to produce a compound represented by chemical formula 1-3, and may be carried out in the same manner as step 1-1 of reaction formula 1, except that the reactive groups for the Suzuki-coupling reaction are different.

[0090] Furthermore, steps 2-2 and 2-3 may be carried out in the same manner as steps 1-2 and 1-3 of reaction equation 1, respectively.

[0091] Furthermore, the compound represented by chemical formula 1 can be produced by the following reaction equation 3, for example, when L is one of the linking groups represented by chemical formulas 2h to 2k.

[0092] [ka] In reaction formula 3, P1 represents a protecting group, as defined in reaction formula 1, and the remaining substituents are as defined in chemical formula 1.

[0093] Step 3-1 is a step in which a compound represented by chemical formula 1-1 and a compound represented by chemical formula 1-9 are reacted to produce a compound represented by chemical formula 1-3. The reaction is a nucleophilic substitution reaction and is preferably carried out in the presence of a base.

[0094] Furthermore, steps 3-2 and 3-3 may be carried out in the same manner as steps 1-2 and 1-3 of reaction equation 1, respectively.

[0095] The manufacturing methods for each of the above-described steps can be further elaborated in the examples described later.

[0096] Furthermore, the present invention provides a pharmaceutical composition containing a compound represented by chemical formula 1, or a pharmaceutically acceptable salt thereof, as an active ingredient.

[0097] More specifically, the present invention can be understood to provide a pharmaceutical composition containing a compound represented by chemical formula 1, its stereoisomer, a mixture of its stereoisomers, its isotopic derivative, its pharmaceutically acceptable salt, or its prodrug as an active ingredient.

[0098] Furthermore, the present invention provides a pharmaceutical composition for the prevention or treatment of inflammatory diseases, autoimmune diseases, or cancer, comprising a compound represented by chemical formula 1, or a pharmaceutically acceptable salt thereof, as an active ingredient.

[0099] More specifically, the present invention can be understood to provide a pharmaceutical composition for the prevention or treatment of inflammatory diseases, autoimmune diseases, or cancers in which the inhibitory effect of ITK and BTK is beneficial, comprising a compound represented by chemical formula 1, its stereoisomer, a mixture of its stereoisomers, its isotopic derivative, its pharmaceutically acceptable salt, or its prodrug as an active ingredient.

[0100] At this time, autoimmune diseases include rheumatoid arthritis, lupus erythematosus, childhood diabetes, psoriasis, aphthous stomatitis, chronic thyroiditis, some acquired aplastic anemia, primary cirrhosis, ulcerative colitis, Behçet's disease, Crohn's disease, silicosis, asbestosis, Sjögren's syndrome, Guillain-Barré syndrome, dermatomyositis, polymyositis, multiple sclerosis, anti-MOG antibody disease, autoimmune hemolytic anemia, autoimmune encephalomyelitis, myasthenia gravis, Graves' hyperthyroidism, polyarteritis nodosa, ankylosing spondylitis, fibrous tissue inflammation, temporal arteritis, Wilson's disease, asthma, neuromyelitis optica, Fanconi syndrome, or degenerative neurological diseases such as Alzheimer's, Parkinson's, and Lou Gehrig's disease. Cancer may be hematological cancer, extranodal marginal B-cell lymphoma, glioblastoma, lymphoplasmacytic lymphoma, acute myeloid leukemia, macroglobulinemia, B-cell lymphoma, chronic lymphocytic leukemia, follicular lymphoma, non-Hodgkin lymphoma, diffuse large B-cell lymphoma, pilocytic cell leukemia, mantle cell lymphoma, glioblastoma, bladder cancer, pancreatic cancer, ovarian cancer, colorectal cancer, kidney cancer, gastric cancer, transitional cell carcinoma, breast carcinoma, breast cancer, non-small cell lung cancer, or multiple myeloma.

[0101] In this invention, the term "prevention" means all actions that suppress or delay the onset, spread, and recurrence of a disease by administering the composition of this invention, and "treatment" means all actions that improve or favorably alter the symptoms of a disease by administering the composition of this invention.

[0102] The pharmaceutical compositions of the present invention can be formulated into oral or parenteral dosage forms by standard pharmaceutical practices. These dosage forms may contain, in addition to the active ingredient, pharmaceutically acceptable additives such as carriers, adjuvants, or diluents.

[0103] Suitable carriers include, for example, physiological saline, polyethylene glycol, ethanol, vegetable oil, and isopropyl myristate. Diluents include, but are not limited to, lactose, dextrose, sucrose, mannitol, sorbitol, cellulose, and / or glycine. Furthermore, the compounds of the present invention can be dissolved in oils, propylene glycol, or other solvents commonly used in the manufacture of injectable solutions. For topical action, the compounds of the present invention can be formulated into ointments or creams.

[0104] The preferred dosage of the compound of the present invention varies depending on the patient's condition and weight, the severity of the disease, the form of the drug, the route of administration, and the duration, but can be appropriately selected by those skilled in the art. However, for the desired effect, it is preferable to administer the compound of the present invention at a dose of 0.0001 to 100 mg / kg (body weight), preferably 0.001 to 100 mg / kg (body weight) per day. The drug may be administered once a day or in divided doses, by oral or parenteral routes.

[0105] Depending on the administration method, the pharmaceutical composition may contain 0.001 to 99% by weight, preferably 0.01 to 60% by weight, of the compound of the present invention.

[0106] The pharmaceutical compositions according to the present invention can be administered to mammals, including mice, rats, livestock, and humans, via a variety of routes. While all methods of administration are conceivable, they can be administered, for example, orally, rectally or intravenously, intramuscularly, subcutaneously, intrauterine dura mater, or intracerebral (intracerebroventricular) injection.

[0107] On the other hand, as used herein, ----- means a bond that is linked to another substituent.

[0108] Furthermore, in this specification, the halogen group means fluoro, chloro, bromo, or iodine.

[0109] Furthermore, in this specification, alkyl groups may be linear or branched. According to one embodiment, the alkyl group has 1 to 10 carbon atoms. According to another embodiment, the alkyl group has 1 to 4 carbon atoms. Specific examples of alkyl groups include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, tert-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, and 2-ethyl Examples include, but are not limited to, butyl, heptyl, n-heptyl, isohexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2,4,4-trimethyl-1-pentyl, 2,4,4-trimethyl-2-pentyl, 2-propylpentyl, n-nonyl, 2,2-dimethylheptyl, or n-decyl. Furthermore, the description for alkyl groups is applicable to haloalkyl groups, except that at least one carbon of the alkyl group is substituted with a halogen group. Similarly, the description for alkyl groups is applicable to alkylene groups, except that they are divalent groups.

[0110] Furthermore, in this specification, the alkenyl group may be linear or branched. In one embodiment, the number of carbon atoms in the alkenyl group is 1 to 4. Specific examples of alkenyl groups include, but are not limited to, vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, or 3-butenyl.

[0111] Furthermore, in this specification, the alkynyl group may be a straight chain. In one embodiment, the number of carbon atoms in the alkynyl group is 1 to 4. Specific examples of alkynyl groups include, but are not limited to, ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 3-butynyl, or 3-butynyl.

[0112] Furthermore, in this specification, an alkoxy group means an alkyl group that is single-bonded to oxygen, and may be linear or branched. In one embodiment, the number of carbon atoms in the alkoxy group is 1 to 10. In another embodiment, the number of carbon atoms in the alkoxy group is 1 to 4. Specific examples of alkoxy groups include methoxy, ethoxy, propoxy, n-propoxy, isopropoxy, butoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, 1-methylbutoxy, 1-ethylbutoxy, pentyloxy, n-pentyloxy, isopentyloxy, neopentyloxy, tert-pentyloxy, 1-ethyl-propoxy, 1,1-dimethylpropoxy, hexyloxy, n-hexyloxy, 1-methylpentyloxy, 2-methylpentyloxy, 4-methyl-2-pentyloxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, and hexyloxy. Examples include, but are not limited to, but but include butyloxy, n-heptyloxy, isohexyloxy, 1-methylhexyloxy, 2-methylhexyloxy, 3-methylhexyloxy, 4-methylhexyloxy, 5-methylhexyloxy, octyloxy, n-octyloxy, tert-octyloxy, 1-methylheptyloxy, 2-ethylhexyloxy, 2,4,4-trimethyl-1-pentyloxy, 2,4,4-trimethyl-2-pentyloxy, 2-propylpentyloxy, n-nonyloxy, 2,2-dimethylheptyloxy, or n-decyloxy. Furthermore, the description of alkoxy groups is applicable to haloalkoxy groups, except that at least one carbon of the alkoxy group is substituted with a halogen group.

[0113] Furthermore, in this specification, a cycloalkyl group is understood to mean a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound that contains only carbon as a ring-forming atom and does not possess aromaticity. In one embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 10. In another embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 8. In yet another embodiment, the number of carbon atoms in the cycloalkyl group is 3 to 7. Specific examples of cycloalkyl groups include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, cyclononyl, or cyclodecyl.

[0114] Furthermore, in this specification, an aryl group is understood to mean a monovalent substituent derived from a monocyclic or fused polycyclic compound that contains only carbon as a ring-forming atom and is aromatic. In one embodiment, the aryl group has 6 to 20 carbon atoms. In another embodiment, the aryl group has 6 to 12 carbon atoms. In yet another embodiment, the aryl group has 6 to 10 carbon atoms. Specific examples of monocyclic aryl groups include, but are not limited to, phenyl, biphenylyl, or terphenylyl. Condensed polycyclic aryl groups include, but are not limited to, naphthyl, anthracenyl, phenanthryl, pyrenyl, perilenyl, or chrysenyl groups.

[0115] Furthermore, in this specification, a nitrogen-containing six-membered heteroaryl compound is understood to mean a monovalent substituent that is aromatic, contains nitrogen in addition to carbon as a ring-forming atom, and is derived from a monocyclic compound with six ring-forming atoms. Specific examples of nitrogen-containing six-membered heteroaryl compounds include, but are not limited to, pyridinyl, pyrimidinyl, pyridadinyl, pyrazinyl, triazinyl, or tetradinyl.

[0116] Furthermore, in this specification, a five-membered or six-membered heterocyclic group is understood to mean a substituent derived from a monocyclic compound with five or six ring-forming atoms, further comprising one to three heteroatoms selected from O, N, and S in addition to carbon as ring-forming atoms. Also, a five-membered or six-membered heterocyclic group is understood to encompass all structures, both aromatic and non-aromatic. Therefore, a five-membered or six-membered heterocyclic group can be understood to include all aromatic heterocycles and their hydrogenated derivatives. Additionally, a five-membered or six-membered heterocyclic group may be oxo (=O) substituted or unsubstituted, where "oxo (=O) substituted" means "containing oxo (=O) substituted carbon (C=O) instead of carbon as a ring-forming atom." Specific examples of five-membered or six-membered heterocyclic groups containing one to three heteroatoms selected from the group consisting of oxo (=O)-substituted or unsubstituted N, O, and S include, but are not limited to, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, thiadiazole, oxadiazole, pyridine, pyrimidine, pyridazine, pyrazine, triazine, tetrazine ring, or pyridine-2(1H)-one. [Effects of the Invention]

[0117] The compound represented by Chemical Formula 1 of the present invention, or a pharmaceutically acceptable salt thereof, can be usefully used for the prevention or treatment of inflammatory diseases, autoimmune diseases, or cancer. [Modes for carrying out the invention]

[0118] The present invention will be described in more detail below with reference to the following examples. However, the following examples are merely illustrative of the present invention, and the scope of the present invention is not limited thereto.

[0119] Manufacturing Example 1: Production of 4,6-dichloro-1-isopropyl-1H-pyrrolo[3,2-c]pyridine [ka]

[0120] 4,6-Dichloro-1H-pyrrolo[3,2-c]pyridine (5.61 g, 30 mmol) was dissolved in DMF (60 mL), and then 2-iodopropane (3.59 mL, 36 mmol) and Cs2CO3 (24 g, 75 mmol) were added. The reaction mixture was gradually heated and stirred at 60 °C for 1 hour. After the mixture was cooled to room temperature, it was diluted with ethyl acetate and then washed with distilled water. The organic layer was dried over MgSO4, filtered and concentrated, and the obtained residue was purified by silica gel chromatography (0 - 50% dichloromethane / hexane) to synthesize white solid 4,6-dichloro-1-isopropyl-1H-pyrrolo[3,2-c]pyridine (5.1 g, 74% yield).

[0121] 1 H NMR (500 MHz, CDCl3) δ 7.28 - 7.24 (m, 2), 6.64 (d, J = 3.0 Hz, 1H), 4.61 - 4.53 (m, 1H), 1.54 (d, J = 7.0, 6H).; LC-MS (ESI) m / z : 229[M+H] +

[0122] Production Example 2. Production of 4,6-dichloro-1-methyl-1H-pyrrolo[3,2-c]pyridine

Chemical formula

[0123] The target compound (82% yield, white solid) was produced in the same manner as in Production Example 1, except that iodomethane was used instead of 2-iodopropane used in Production Example 1.

[0124] 1 H NMR (500 MHz, CDCl3) δ 7.21 (s, 1H), 7.10 (d, J = 3.2 Hz, 1H), 6.60 (d, J = 3.2 Hz, 1H), 3.78 (s, 3H).; LC-MS (ESI) m / z : 201[M+H] +

[0125] Production Example 3. Production of 4,6-dichloro-1-ethyl-1H-pyrrolo[3,2-c]pyridine [ka]

[0126] The target compound (80% yield, white solid) was produced in the same manner as in Production Example 1, except that iodoethane was used instead of 2-iodopropane as in Production Example 1.

[0127] LC-MS (ESI) m / z: 215[M+H] +

[0128] Manufacturing Example 4. Production of 4,6-dichloro-1-propyl-1H-pyrrolo[3,2-c]pyridine [ka]

[0129] The target compound (81% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 1-iodopropane was used instead of 2-iodopropane as in Preparation Example 1.

[0130] LC-MS (ESI) m / z: 229[M+H] +

[0131] Manufacturing Example 5. Production of 1-butyl-4,6-dichloro-1H-pyrrolo[3,2-c]pyridine [ka]

[0132] The target compound (77% yield, yellow oil) was produced in the same manner as in Production Example 1, except that 1-iodopropane was used instead of 2-iodopropane as in Production Example 1.

[0133] LC-MS (ESI) m / z: 243 [M+H] +

[0134] Production Example 6. Production of 4,6-dichloro-1-isobutyl-1H-pyrrolo[3,2-c]pyridine

Chemical Structure

[0135] The target compound (84% yield, colorless oil) was produced in the same manner as in Production Example 1, except that 1-bromo-2-methylpropane was used instead of 2-iodopropane used in Production Example 1.

[0136] LC-MS (ESI) m / z: 243 [M+H] +

[0137] Production Example 7. Production of (S)-1-(sec-butyl)-4,6-dichloro-1H-pyrrolo[3,2-c]pyridine

Chemical Structure

[0138] The target compound (80% yield, colorless oil) was produced in the same manner as in Production Example 1, except that (R)-sec-butyl 4-methylbenzenesulfonate was used instead of 2-iodopropane used in Production Example 1.

[0139] LC-MS (ESI) m / z: 243 [M+H] +

[0140] Production Example 8. Production of (R)-1-(sec-butyl)-4,6-dichloro-1H-pyrrolo[3,2-c]pyridine

Chemical Structure

[0141] The target compound (86% yield, colorless oil) was produced in the same manner as in Production Example 1, except that (S)-sec-butyl 4-methylbenzenesulfonate was used instead of 2-iodopropane as in Production Example 1.

[0142] LC-MS (ESI) m / z: 243[M+H] +

[0143] Manufacturing Example 9. Production of 4,6-dichloro-1-(cyclopropylmethyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0144] The target compound (90% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that (bromomethyl)cyclopropane was used instead of 2-iodopropane as in Preparation Example 1.

[0145] LC-MS (ESI) m / z: 241[M+H] +

[0146] Manufacturing Example 10. Production of 4,6-dichloro-1-(2-methylbutyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0147] The target compound (80% yield, colorless oil) was produced in the same manner as in Production Example 1, except that 1-bromo-2-methylbutane was used instead of 2-iodopropane as in Production Example 1.

[0148] LC-MS (ESI) m / z: 257[M+H] +

[0149] Production Example 11. Production of 4,6-dichloro-1-cyclopentyl-1H-pyrrolo[3,2-c]pyridine [ka]

[0150] The target compound (30% yield, white solid) was produced in the same manner as in Production Example 1, except that bromocyclopentane was used instead of 2-iodopropane used in Production Example 1.

[0151] LC-MS (ESI) m / z : 255[M+H] +

[0152] Production Example 12. Production of 4,6-dichloro-1-(cyclobutylmethyl)-1H-pyrrolo[3,2-c]pyridine

Chemical formula

[0153] The target compound (30% yield, yellow solid) was produced in the same manner as in Production Example 1, except that (bromomethyl)cyclobutane was used instead of 2-iodopropane used in Production Example 1.

[0154] LC-MS (ESI) m / z : 255[M+H] +

[0155] Production Example 13. Production of 4,6-dichloro-1-(cyclopentylmethyl)-1H-pyrrolo[3,2-c]pyridine

Chemical formula

[0156] The target compound (69% yield, white solid) was produced in the same manner as in Production Example 1, except that (bromomethyl)cyclopentane was used instead of 2-iodopropane used in Production Example 1.

[0157] LC-MS (ESI) m / z : 269 [M+H] +

[0158] Production Example 14. Production of 4,6-dichloro-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0159] The target compound (48% yield, yellow solid) was prepared in the same manner as in Preparation Example 1, except that 3-(bromomethyl)tetrahydrofuran was used instead of 2-iodopropane as in Preparation Example 1.

[0160] LC-MS (ESI) m / z: 271[M+H] +

[0161] Manufacturing Example 15. Production of 4,6-dichloro-1-(3,3-dimethylbutyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0162] The target compound (88% yield, yellow solid) was prepared in the same manner as in Preparation Example 1, except that 1-bromo-3,3-dimethylbutane was used instead of 2-iodopropane as in Preparation Example 1.

[0163] LC-MS (ESI) m / z: 271[M+H] +

[0164] Manufacturing Example 16. Production of 4,6-dichloro-1-(cyclohexylmethyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0165] The target compound (73% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that (bromomethyl)cyclohexane was used instead of 2-iodopropane as used in Preparation Example 1.

[0166] LC-MS (ESI) m / z: 283[M+H] +

[0167] Manufacturing Example 17. Production of 4,6-dichloro-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0168] The target compound (51% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 4-(bromomethyl)tetrahydro-2H-pyran was used instead of 2-iodopropane as used in Preparation Example 1.

[0169] LC-MS (ESI) m / z: 285[M+H] +

[0170] Production Example 18. Production of 4,6-dichloro-1-(2-methoxyethyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0171] The target compound (80% yield, yellow solid) was prepared in the same manner as in Preparation Example 1, except that 1-bromo-2-methoxyethane was used instead of 2-iodopropane as in Preparation Example 1.

[0172] LC-MS (ESI) m / z: 245[M+H] +

[0173] Production Example 19. Production of 1-benzyl-4,6-dichloro-1H-pyrrolo[3,2-c]pyridine [ka]

[0174] The target compound (67% yield, yellow syrup) was produced in the same manner as in Production Example 1, except that (chloromethyl)benzene was used instead of 2-iodopropane as in Production Example 1.

[0175] LC-MS (ESI) m / z: 277[M+H] +

[0176] Production Example 20. Production of 4,6-dichloro-1-phenethyl-1H-pyrrolo[3,2-c]pyridine [ka]

[0177] The target compound (77% yield, colorless syrup) was produced in the same manner as in Production Example 1, except that (2-chloroethyl)benzene was used instead of 2-iodopropane as in Production Example 1.

[0178] LC-MS (ESI) m / z: 291[M+H] +

[0179] Manufacturing Example 21. Production of 4,6-dichloro-1-(difluoromethyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0180] The target compound (30% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that methyl 2-chloro-2,2-difluoroacetate was used instead of 2-iodopropane as used in Preparation Example 1.

[0181] LC-MS (ESI) m / z: 237[M+H] +

[0182] Production Example 22. Preparation of 4,6-dichloro-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0183] The target compound (85% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 2,2,2-trifluoroethyltrifluoromethanesulfonate was used instead of 2-iodopropane as in Preparation Example 1.

[0184] LC-MS (ESI) m / z: 269[M+H] +

[0185] Production Example 23. Production of 4,6-dichloro-1-(2,2-difluoroethyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0186] The target compound (93% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 2-bromo-1,1-difluoroethane was used instead of 2-iodopropane as in Preparation Example 1.

[0187] LC-MS (ESI) m / z: 251[M+H] +

[0188] Manufacturing Example 24. Production of 4,6-dichloro-1-(2,2-difluorocyclopropyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0189] The target compound (76% yield, yellow solid) was prepared in the same manner as in Preparation Example 1, except that 2-bromo-1,1-difluorocyclopropane was used instead of 2-iodopropane as in Preparation Example 1.

[0190] LC-MS (ESI) m / z: 263[M+H] +

[0191] Manufacturing Example 25. Production of (R)-4,6-dichloro-1-(1,1,1-trifluoropropan-2-yl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0192] The target compound (39% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that (S)-1,1,1-trifluoropropane-2-yltrifluoromethanesulfonate was used instead of 2-iodopropane as used in Preparation Example 1.

[0193] LC-MS (ESI) m / z: 283[M+H] +

[0194] Manufacturing Example 26. Production of 4,6-dichloro-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0195] The target compound (48% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 1-(bromomethyl)-1-(trifluoromethyl)cyclopropane was used instead of 2-iodopropane as used in Preparation Example 1.

[0196] LC-MS (ESI) m / z: 309[M+H] +

[0197] Manufacturing Example 27. Production of 4,6-dichloro-1-((4,4-difluorocyclohexyl)methyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0198] The target compound (59% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 4-(bromomethyl)-1,1-difluorocyclohexane was used instead of 2-iodopropane as used in Preparation Example 1.

[0199] LC-MS (ESI) m / z: 319[M+H] +

[0200] Manufacturing Example 28. Production of 2-(4,6-dichloro-1H-pyrrolo[3,2-c]pyridine-1-yl)-2-methylpropanenitrile [ka]

[0201] Step 1. Preparation of 2-(4,6-dichloro-1H-pyrrolo[3,2-c]pyridine-1-yl)acetonitrile 4,6-Dichloro-1H-pyrrolo[3,2-c]pyridine (2.0 g, 10.7 mmol) was dissolved in DMF (20 mL), and then 2-bromoacetonitrile (0.89 mL, 12.4 mmol) and Cs2CO3 (5.23 g, 16.0 mmol) were added. The reaction mixture was gradually heated and stirred at 60°C for 1 hour. After the mixture cooled to room temperature, it was diluted with ethyl acetate and washed with distilled water. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0-50% ethyl acetate / hexane) to synthesize 2-(4,6-dichloro-1H-pyrrolo[3,2-c]pyridine-1-yl)acetonitrile (1.78 g, 74% yield) as a light brown solid.

[0202] 1 H NMR (500 MHz, DMSO-d6) δ 7.96 (s, 1H), 7.74 (d, J = 3.4 Hz, 1H), 6.73 (d, J = 3.2 Hz, 1H), 5.60 (s, 2H).;LC-MS (ESI) m / z : 226[M+H] +

[0203] Step 2. Preparation of 2-(4,6-dichloro-1H-pyrrolo[3,2-c]pyridine-1-yl)-2-methylpropanenitrile 2-(4,6-dichloro-1H-pyrrolo[3,2-c]pyridine-1-yl)acetonitrile (1.78 g, 7.9 mmol) prepared in step 1 was dissolved in DMF (20 mL), and then 60% NaH (0.79 g, 19.8 mmol) was slowly added at 0°C. The reaction mixture was stirred at 0°C for 5 minutes, and then MeI (1.5 mL, 24 mmol) was slowly added, and the mixture was reacted at room temperature for 30 minutes. After neutralizing the reaction mixture with 1 M aqueous HCl, it was diluted with ethyl acetate and washed with distilled water. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (20-30% ethyl acetate / hexane) to obtain the target compound (1.0 g, 50% yield) as a pale white solid.

[0204] 1 LC-MS (ESI) m / z : 226[M+H] +

[0205] Production Example 29. Production of 4,6-dichloro-1-isopentyl-1H-pyrrolo[3,2-c]pyridine [ka]

[0206] The target compound (73% yield, yellow solid) was prepared in the same manner as in Preparation Example 1, except that 1-bromo-3-methylbutane was used instead of 2-iodopropane as in Preparation Example 1.

[0207] LC-MS (ESI) m / z: 257[M+H] +

[0208] Manufacturing Example 30. Production of 4,6-dichloro-1-(pyridine-2-ylmethyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0209] The target compound (77% yield, yellow solid) was prepared in the same manner as in Preparation Example 1, except that 2-(chloromethyl)pyridine was used instead of 2-iodopropane as in Preparation Example 1.

[0210] LC-MS (ESI) m / z: 278[M+H] +

[0211] Manufacturing Example 31. Production of 1-(4,6-dichloro-1H-pyrrolo[3,2-c]pyridine-1-yl)-2-methylpropan-2-ol [ka]

[0212] The target compound (80% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 2,2-dimethyloxirane was used instead of iodopropane as in Preparation Example 1.

[0213] LC-MS (ESI) m / z: 259[M+H] +

[0214] Production Example 32. Preparation of 4,6-dichloro-1-(2-fluoroethyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0215] The target compound (72% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 1-fluoro-2-iodoethane was used instead of the iodopropane used in Preparation Example 1.

[0216] LC-MS (ESI) m / z: 233[M+H] +

[0217] Manufacturing Example 33. Production of 4,6-dichloro-1-(3-fluoropropyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0218] The target compound (78% yield, white solid) was prepared in the same manner as in Preparation Example 1, except that 1-iodo-3-fluoropropane was used instead of the iodopropane used in Preparation Example 1.

[0219] LC-MS (ESI) m / z: 247[M+H] +

[0220] Manufacturing Example 34. Production of (R)-4,6-dichloro-1-(2-methylbutyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0221] The target compound (80% yield, colorless oil) was produced in the same manner as in Production Example 1, except that (2R)-1-bromo-2-methylbutane was used instead of 2-iodopropane as in Production Example 1.

[0222] LC-MS (ESI) m / z: 257[M+H] +

[0223] Production Example 35. Production of (S)-4,6-dichloro-1-(2-methylbutyl)-1H-pyrrolo[3,2-c]pyridine [ka]

[0224] The target compound (80% yield, colorless oil) was produced in the same manner as in Production Example 1, except that (2S)-1-bromo-2-methylbutane was used instead of 2-iodopropane as in Production Example 1.

[0225] LC-MS (ESI) m / z: 257[M+H] +

[0226] Example 1. Preparation of 1-(4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one [ka]

[0227] Step 1. Preparation of tert-butyl 4-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate 4,6-Dichloro-1-methyl-1H-pyrrolo[3,2-c]pyridine (201 mg, 1.0 mmol) was dissolved in 1,4-dioxane (3.0 mL), and then tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate (371 mg, 1.2 mmol), Pd(PPh3)4 (116 mg, 0.10 mmol), and 1 M Na2CO3 aqueous solution (2.0 mL) were added at room temperature. The reaction mixture was gradually heated and stirred at 80°C for 1 hour. After the mixture cooled to room temperature, it was diluted with ethyl acetate and washed with distilled water. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0-40% ethyl acetate / hexane) to synthesize tert-butyl 4-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate (238 mg, 68% yield) as a white solid.

[0228] 1 H NMR (500 MHz, CDCl3) δ 7.15 (s, 1H), 7.07 (d, J = 3.2 Hz, 1H), 6.67 (d, J = 3.0 Hz, 1H), 6.48 (br s, 1H), 4.17 (br s, 2H), 3.76 (s, 3H), 3.67 (br s, 2H), 2.80 (br s, 2H), 1.50 (s, 9H).; LC-MS (ESI) m / z : 348[M+H] +

[0229] Step 2. Preparation of tert-butyl 4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate 235 mg, 0.68 mmol of tert-butyl 4-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate was dissolved in 4.0 mL of 1,4-dioxane. At room temperature, 117 mg, 1.0 mmol of 5-methylthiazole-2-amine, 62 mg of Pd2(dba)3, 79 mg of Xantphos, and 553 mg of Cs2CO3 were added. The reaction mixture was incubated in a microwave reactor at 160°C for 2 hours. The mixture was diluted with ethyl acetate, washed with distilled water, dried over MgSO4, filtered and concentrated, and the resulting residue was purified by silica gel chromatography (0-70% ethyl acetate / hexane) to synthesize tert-butyl 4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate (30 mg, 10% yield) as a yellow solid.

[0230] 1H NMR (500 MHz, CDCl3) δ 8.92 (br s, 1H), 7.01 (d, J = 1.0 Hz, 1H), 6.96 (d, J = 3.3 Hz, 1H), 6.68 (br s, 1H), 6.63 (d, J = 3.1 Hz, 1H), 6.56 (m, 1H), 4.21 (br s, 2H), 3.74 (br s, 2H), 3.72 (s, 3H), 2.95 (br s, 2H), 2.41 (s, 3H), 1.52 (s, 9H).; LC-MS (ESI) m / z : 426 [M+H] +

[0231] Step 3. Preparation of 1-(4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one 30 mg, 0.070 mmol of tert-butyl 4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate was dissolved in CH2Cl2 (3.0 mL), then TFA (2.0 mL) was added, and the mixture was stirred at room temperature for 1 hour. After the reaction was complete, the mixture was concentrated under reduced pressure to synthesize the salt compound. The obtained salt compound was dissolved in water (2.0 mL) and THF (4.0 mL), then NaHCO3 (60 mg, 0.72 mmol) was added, and the mixture was stirred at room temperature for 10 minutes. After the mixture was cooled to 0°C, 1.0 M acryloyl chloride (0.091 mL, 1.3 eq) diluted with THF was slowly added dropwise. The reaction mixture was stirred at room temperature for 30 minutes, diluted with dichloromethane, and washed with distilled water and brine. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0-10% methanol / dichloromethane) to synthesize 1-(4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one (14 mg, 52% yield) as a white solid.

[0232] 1 H NMR (500 MHz, DMSO-d6) δ 10.66 (s, 1H), 7.29 (d, J = 2.9 Hz, 1H), 6.96 (s, 1H), 6.89 (m, 1H), 687 (s, 1H), 6.65 (m, 1H), 6.61 (br s, 1H), 6.17 (dd, J = 16.7, 4.9 Hz, 1H), 5.73 (m, 1H), 4.35 (d, J = 52.5 Hz, 2H), 3.84 (dt, J = 17.8, 5.2 Hz, 2H), 3.68 (s, 3H), 2.89 (d, J = 37.3 Hz, 2H), 2.31 (s, 3H).; LC-MS (ESI) m / z : 380 [M+H] +

[0233] Examples 2 to 49 were prepared using a method similar to that of Example 1, and the structures and analytical results of the compounds are summarized in Table 1 below.

[0234] [Table 1] TIFF2026516449000051.tif236170TIFF2026516449000052.tif242157TIFF2026516449000053.tif251169TIFF202 6516449000054.tif242155TIFF2026516449000055.tif242156TIFF2026516449000056.tif237170TIFF20265164490 00057.tif238160TIFF2026516449000058.tif250169TIFF2026516449000059.tif244162TIFF2026516449000060.t if242160TIFF2026516449000061.tif243160TIFF2026516449000062.tif243155TIFF2026516449000063.tif208160

[0235] Example 50. Preparation of N-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide [ka]

[0236] Step 1. Preparation of tert-butyl(3-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)carbamate Tert-butyl (3-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)carbamate (52% yield) was synthesized in the same manner as in step 1 of Example 1, except that (3-((tert-butoxycarbonyl)amino)phenyl)boronic acid was used instead of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-1(2H)-carboxylate used in synthesis step 1 of Example 1.

[0237] LC-MS (ESI) m / z: 358 [M+H] +

[0238] Step 2. Preparation of tert-butyl(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)carbamate tert-butyl(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)carbamate (27% yield) was synthesized in the same manner as in step 2 of Example 1, except that tert-butyl(3-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)carbamate was used instead of tert-butyl4-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)carbamate in step 2 of Example 1.

[0239] 1 H NMR (500 MHz, CDCl3) δ 8.53 (s, 1H), 8.12 (s, 1H), 7.82 (d, J = 6.9 Hz, 1H), 7.46 (m, 2H), 7.01 (m, 2H), 6.79 (m, 2H), 6.63 (s, 1H), 3.75 (s, 3H), 2.39 (s, 3H), 1.54 (s, 9H).; LC-MS (ESI) m / z : 436 [M+H] +

[0240] Step 3. Preparation of N-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide N-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide (77% yield) was synthesized in the same manner as in step 3 of Example 1, except that tert-butyl(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)carbamate was used instead of tert-butyl4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide (77% yield) was synthesized in the same manner as in step 3 of Example 1, except that tert-butyl(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide (77% yield) was used instead of tert-butyl4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)carbamate was used instead of tert-butyl4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide (77% yield) was used in step 3 of Example 1.

[0241] 1H NMR (500 MHz, DMSO-d6) δ 11.28 (br s, 1H), 10.36 (s, 1H), 8.66 (s, 1H), 7.89 (d, J = 7.7 Hz, 1H), 7.66 (d, J = 7.9 Hz, 1H), 7.54 (t, J = 7.9 Hz, 1H), 7.45 (d, J = 3.2 Hz, 1H), 7.09 (s, 1H), 7.03 (s, 1H), 6.82 (d, J = 3.1 Hz, 1H), 6.50 (dd, J = 16.9, 10.1 Hz, 1H), 6.31 (dd, J = 16.9, 1.6 Hz, 1H), 5.80 (dd, J = 10.2, 1.6 Hz, 1H), 3.76 (s, 3H), 2.34 (s, 3H).; LC-MS (ESI) m / z : 390 [M+H] +

[0242] Examples 51 to 78 were prepared using a method similar to that of Example 50, and the structures and analytical results of the compounds are summarized in Table 2 below.

[0243] [Table 2] TIFF2026516449000066.tif243162TIFF2026516449000067.tif246161TIFF2026516449000068.tif244162TIFF2026516449 000069.tif246162TIFF2026516449000070.tif245163TIFF2026516449000071.tif245161TIFF2026516449000072.tif33163

[0244] Example 79. Preparation of (S)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one [ka]

[0245] Step 1. Preparation of tert-butyl(S)-3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate 307 mg, 1.64 mmol of tert-butyl(S)-3-hydroxypiperidine-1-carboxylate was dissolved in 5.0 mL of DMF, and then 66 mg, 1.64 mmol of 60% NaH was slowly added at 0°C. The reaction mixture was stirred at 0°C for 30 minutes, after which 250 mg, 1.09 mmol of 4,6-dichloro-1-isopropyl-1H-pyrrolo[3,2-c]pyridine was added and the mixture was reacted at 100°C for 2 hours. After the reaction mixture cooled to room temperature, it was diluted with ethyl acetate and washed with aqueous ammonium chloride solution. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0-30% ethyl acetate / hexane) to synthesize tert-butyl(S)-3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate (242 mg, 58% yield) as a white solid.

[0246] 1 H NMR (500 MHz, CDCl3) δ 7.08 (m, 1H), 6.94 (m, 1H), 6.55 (d, J = 2.8 Hz, 1H), 5.76 (d, J = 19.2 Hz, 1H), 4.51 (m, 1H), 3.77-3.47 (m, 4H), 2.20 (m, 2H), 1.54-1.43 (m, 15H).; LC-MS (ESI) m / z : 380 [M+H] +

[0247] Step 2. Preparation of tert-butyl(S)-3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate tert-butyl(S)-3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate (21% yield) was synthesized in the same manner as in step 2 of Example 1, except that tert-butyl(S)-3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate was used instead of tert-butyl4-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate was used in step 2 of Example 1.

[0248] LC-MS (ESI) m / z: 458 [M+H] +

[0249] Step 3. Preparation of (S)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one (S)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one (69% yield) was synthesized in the same manner as in step 3 of Example 1, except that tert-butyl(S)-3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one (69% yield).

[0250] 1H NMR (500 MHz, DMSO-d6)δ 10.61 (s, 1H), 7.25 (t, J = 3.0 Hz, 1H), 6.97 (s, 1H), 6.72-6.50 (m, 2H), 6.37 (s, 1H), 6.14 (ddd, J = 16.7, 5.7, 2.0 Hz, 1H), 5.90 (d, J = 42.7 Hz, 1H), 5.66 (ddd, J = 26.2, 10.3, 1.9 Hz, 1H), 4.45 (m, 1H), 4.10-3.47 (m, 4H), 2.44-2.15 (m, 5H), 1.41 (d, J = 6.6 Hz, 6H).; LC-MS (ESI) m / z : 412 [M+H] +

[0251] Examples 80-204 were prepared using a method similar to that of Example 79, and the structures and analytical results of the compounds are summarized in Table 3 below.

[0252] [Table 3] TIFF2026516449000075.tif245160TIFF2026516449000076.tif242158TIFF2026516449000077.tif243164TIFF2026516449000078.tif244165TIFF2026516449000079.tif242161TIFF2026516449000080.tif245164TIFF2026516449000081.tif244163TIFF2026516449000082.tif218163TIFF2026516449000083.tif232162TIFF2026516449000084.tif243167TIFF2026516449000085.tif246167TIFF2026516449000086.tif235167TIFF2026516449000087.tif234163TIFF2026516449000088.tif238163TIFF2026516449000089.tif220167TIFF2026516449000090.tif243168TIFF2026516449000091.tif245163TIFF2026516449000092.tif244161TIFF2026516449000093.tif247163TIFF2026516449000094.tif248163TIFF2026516449000095.tif222166TIFF2026516449000096.tif243164TIFF2026516449000097.tif247168TIFF2026516449000098.tif246165TIFF2026516449000099.tif248163TIFF2026516449000100.tif227164TIFF2026516449000101.tif226165TIFF2026516449000102.tif237166TIFF2026516449000103.tif244161TIFF2026516449000104.tif220163TIFF2026516449000105.tif246162TIFF2026516449000106.tif89165

[0253] Example 205. Preparation of (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one [ka]

[0254] Step 1. Preparation of tert-butyl(S)-3-((6-chloro-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate 4,6-Dichloro-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine (269 mg, 1.0 mmol) was dissolved in 1,4-dioxane (4.0 mL), and then tert-butyl(S)-3-hydroxypyrrolidine-1-carboxylate (225 mg, 1.2 mmol), Pd2(dba)3 (46 mg, 0.05 mmol), (S)-(-)-BINAP (62 mg, 0.1 mmol), and Cs2CO3 (651 mg, 2.0 mmol) were added at room temperature. The reaction mixture was reacted in a microwave reactor at 130°C for 1 hour. The mixture was diluted with ethyl acetate, washed with distilled water, dried over MgSO4, filtered and concentrated, and the resulting residue was purified by silica gel chromatography (0-30% ethyl acetate / hexane) to synthesize tert-butyl(S)-3-((6-chloro-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate (268 mg, 64% yield) as a white solid.

[0255] 1H NMR (500 MHz, CDCl3) δ 7.02-6.91 (m, 2H), 6.65 (d, J = 2.9 Hz, 1H), 5.76 (d, J = 18.8 Hz, 2H), 4.56 (q, J = 8.4 Hz, 2H), 3.77-3.48 (m, 4H), 2.22 (br s, 2H), 1.47 (d, J = 7.3 Hz, 9H).; LC-MS (ESI) m / z : 420 [M+H] +

[0256] Step 2. Preparation of tert-butyl(S)-3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate tert-butyl(S)-3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate (39% yield) was synthesized in the same manner as in step 2 of Example 1, except that tert-butyl(S)-3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate was used instead of tert-butyl4-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate was used in step 2 of Example 1.

[0257] 1H NMR (500 MHz, CDCl3) δ 8.96 (s, 1H), 7.00 (d, J = 6.0 Hz, 1H), 6.87 (s, 1H), 6.59 (s, 1H), 6.40 (d, J = 13.6 Hz, 1H), 5.94 (d, J = 18.0 LC-MS (ESI) m / z : 498 [M+H] +

[0258] Step 3. Preparation of (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one Instead of tert-butyl4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate used in synthesis step 3 of Example 1, tert-butyl(S)-3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[ (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one (64% yield) was synthesized in the same manner as in step 3 of Example 1, except that 3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one (64% yield).

[0259] 1H NMR (500 MHz, DMSO-d6)δ 10.73 (s, 1H), 7.17 (t, J = 2.6 Hz, 1H), 6.98 (s, 1H), 6.72 (d, J = 4.4 Hz, 1H), 6.60 (ddd, J = 50.6, 16.7, 10.3 Hz, 1H), 6.47 (s, 1H), 6.15 (ddd, J = 16.7, 7.3, 2.2 Hz, 1H), 5.91 (d, J = 42.8 Hz, 1H), 5.67 (ddd, J = 27.1, 10.3, 2.2 Hz, 1H), 5.05 (q, J = 9.1 Hz, 2H), 4.11-3.48 (m, 4H), 2.44-2.16 (m, 5H).; LC-MS (ESI) m / z : 452 [M+H] +

[0260] Examples 206-223 were prepared using a method similar to that of Example 205, and the structures and analytical results of the compounds are summarized in Table 4 below.

[0261] [Table 4] TIFF2026516449000109.tif243158TIFF2026516449000110.tif254170TIFF2026516449 000111.tif240168TIFF2026516449000112.tif248169TIFF2026516449000113.tif60168

[0262] Example 224. Preparation of (S)-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one [ka]

[0263] Step 1. Preparation of tert-butyl(S)-3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate After dissolving tert-butyl(S)-3-hydroxypyrrolidine-1-carboxylate (1.76 g, 9.4 mmol) in THF (10.0 mL), 60% NaH (469 mg, 11.2 mmol) was slowly added at 0°C. The reaction mixture was stirred at 0°C for 30 minutes, then 4,6-dichloro-1-isopropyl-1H-pyrrolo[3,2-c]pyridine (1.90 g, 7.8 mmol) was added, and the mixture was reacted at 60°C for 6 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate and washed with aqueous ammonium chloride solution. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0-30% ethyl acetate / hexane) to synthesize tert-butyl(S)-3-((6-chloro-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate (2.00 g, 65% yield) as a white solid.

[0264] 1 H NMR (500 MHz, DMSO-d6)δ 7.40-7.27 (m, 2H), 6.48 (s, 1H), 5.57 (d, J = 23.4 Hz, 1H), 3.96 (d, J = 7.3 Hz, 2H), 3.70-3.56 (m, 2H), 3.45 (d, J = 9.1 Hz, 2H), 2.26-2.00 (m, 3H), 1.39 (d, J = 12.5 Hz, 9H), 0.81 (d, J = 6.6 Hz, 6H).; LC-MS (ESI) m / z : 394 [M+H] +

[0265] Step 2. Preparation of tert-butyl(S)-3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate tert-butyl(S)-3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate (42% yield) was synthesized in the same manner as in step 2 of Example 1, except that tert-butyl(S)-3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate was used instead of tert-butyl4-(6-chloro-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate, which was used in step 2 of Example 1.

[0266] LC-MS (ESI) m / z: 472 [M+H] +

[0267] Step 3. Preparation of (S)-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one 118 mg, 0.25 mmol of tert-butyl(S)-3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate (118 mg, 0.25 mmol) was dissolved in CH2Cl2 (2.0 mL), then 1.5 mL of TFA was added, and the mixture was stirred at room temperature for 1 hour. After the reaction was complete, the mixture was concentrated under reduced pressure to synthesize the salt compound. The obtained salt compound was dissolved in DMF (2.0 mL), then DIPEA (0.28 mL, 1.6 mmol), 2-fluoroacrylic acid (34 mg, 0.38 mmol), and HATU (115 mg, 0.30 mmol) were added, and the mixture was stirred at room temperature for 15 hours. The reaction product was diluted with ethyl acetate and washed with distilled water and brine. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (70% ethyl acetate / hexane) to synthesize the white solid (S)-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one (45 mg, 41% yield).

[0268] 1 H NMR (500 MHz, CDCl3) δ 7.05 (d, J = 4.5 Hz, 1H), 6.83 (s, 1H), 6.48-6.43 (m, 1H), 6.41 (d, J = 5.1 Hz, 1H), 6.02 (d, J = 18.7 Hz, 1H), 5.56 (dd, J = 46.8, 2.9 Hz, 1H), 5.13 (ddd, J = 22.1, 16.1, 2.8 Hz, 1H), 4.18-3.67 (m, 6H), 2.53-2.22 (m, 5H), 2.15 (m, 1H), 0.93 (dd, J = 6.3, 1.8 Hz, 6H).; LC-MS (ESI) m / z: 444 [M+H] +

[0269] Examples 225-231 were prepared using a method similar to that of Example 224, and the structures and analytical results of the compounds are summarized in Table 5 below.

[0270] [Table 5] TIFF2026516449000116.tif212168

[0271] Experimental example: Inhibitory activity against BTK and ITK The inhibitory activity of the compounds prepared in the examples against BTK and ITK was measured as follows.

[0272] The inhibitory activity evaluation against BTK and ITK was performed using Promega's "ADP-Glo TM The results were measured using a kinase assay. This assay quantifies the amount of ADP produced during the kinase reaction to measure activation, and was used to measure inhibitory activity against BTK and ITK.

[0273] Specifically, inhibitory activity against BTK and ITK kinases was measured using BTK kinase (Signalchem, B10-10H), ITK kinase (Signalchem, I13-11G-10), and the ADP-Glo ​​kinase assay kit (Promega, V9102). Recombinant purified human BTK and ITK were diluted in 1x kinase reaction buffer (40 mM Tris-Cl, pH 7.5, 20 mM MgCl2, 0.1 mg / mL BSA, 2 mM MnCl2, and 50 μM DTT) and added to 96-well plates (ITK: final concentration 4 ng per reaction / BTK: final concentration 10 ng per reaction). The compounds prepared in the examples were treated to ultimately form a 1% DMSO aqueous solution. The enzymatic reaction was initiated by adding a substrate cocktail containing ATP (1 mM or Km ATP (BTK: 10 μM / ITK: 25 μM)) and 0.2 μg / µl of Poly(Glu4, Tyr1) peptide (final concentrations of BTK and ITK) to a 96-well plate in a total of 25 μL of reactant. After 1 hour of incubation (30°C), an equivalent volume (25 μL per reaction) of ADP Glo was added, and the mixture was incubated at room temperature for 40 minutes (30°C). Next, kinase detection reagent (45 μL per reaction) was added, and the mixture was incubated at room temperature for 30 minutes (30°C). Kinase activity was measured by chemiluminescence according to the ADP Glo kinase assay kit instructions, and the inhibitory activity of the compounds according to the present invention was calculated. The results for each compound were analyzed using Microsoft Excel, and IC50 was performed. 50 The values ​​were calculated using GraphPad Prism software.

[0274] Derived IC 50 Depending on the range of values, the inhibitory activity of each compound was classified into A, B, C, and D as shown below in Table 6. A: Derived IC 50 If the value is 20 nM or less B: Derived IC 50 If the value exceeds 20 nM but is 100 nM or less C: Derived IC 50 If the value exceeds 100 nM and is 500 nM or less D: Derived IC 50 If the value exceeds 500 nM

[0275] [Table 6] TIFF2026516449000118.tif243155TIFF2026516449000119.tif178165

Claims

1. A compound represented by the following chemical formula 1, or a pharmaceutically acceptable salt thereof. 【Chemistry 1】 In chemical formula 1, Y １ is a single bond, C １－４ Alkylene, or C １－４ It is a haloalkylene, R １ is C １－１０ Alkyl, C １－１０ Alkoxy, C ３－１０ Cycloalkyl, C ６－２０ The aryl, N-containing 6-membered heteroaryl, tetrahydrofuranil, or tetrahydropyranil are available. Here, R １ is unsubstituted or substituted with one or more substituents selected from the group consisting of halogen, cyano, hydroxy, C １－４ alkyl and C １－４ haloalkyl, A is a benzene ring, or a five-membered or six-membered heteroring containing one to three heteroatoms selected from the group consisting of substituted or unsubstituted N, O, and S atoms, wherein the five-membered or six-membered heteroring contains at least one N atom. R ２ These are, independently, hydrogen, halogen, cyano, and C. １－４ Alkyl, C １－４ Haloalkyl, C １－４ Alkoxy, C １－４ Haloalkoxy, or -CONH(C) １－４ It is alkyl, k is either 1 or 2, Y ２ is a single bond, -O-, or -O-(C １－４ Alkilen) L is one of the linking groups represented by the following chemical formulas 2a to 2k. 【Chemistry 2】 In chemical formulas 2a to 2k, n is 0, 1, 2, or 3. Z is independent of halogen and C. １－４ Alkyl, C １－４ Haloalkyl, C １－４ Alkoxy, or C １－４ It is a haloalkoxy, Each of a is independently 0, 1, or 2. L' is methylene, ethylene, or methylene-O-methylene. v and w are independently 0, 1, or 2. However, v + w is an integer between 0 and 3. p to s are each independently 0, 1, 2, 3, or 4. However, p+q and r+s are integers between 2 and 4, * represents Y in the above chemical formula 1. ２ It means a point connected to, X is CO or SO ２ And, R ３ is C １－４ Alkyl, C ２－４ Alkenyl, or C ２－４ It is Alkinili, Here, R ３ is either unsubstituted or halogen, NH ２ NH(C １－４ Alkyl) and N(C) １－４ Alkyl) ２ It is substituted with one or more substituents selected from the group consisting of the following.

2. Y １ It is a single bond, methylene, or ethylene. The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

3. R １ These are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl, isohexyl, methoxy, ethoxy, propoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyridinyl, tetrahydrofuranyl, or tetrahydropyranyl. Here, R １ It is either unsubstituted or substituted with one to three substituents selected from the group consisting of chloro, fluoro, cyano, hydroxy, methyl, monofluoromethyl, difluoromethyl, and trifluoromethyl. The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

4. A is benzene, thiazole, thiadiazole, imidazole, pyrazole, pyrazine, pyridine, pyrimidine, or pyridine-2(1H)-one ring. The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

5. R ２ is hydrogen, chloro, fluoro, cyano, methyl, ethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxy, or -CONH(methyl). The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

6. Y ２ It is a single bond, -O-, or -O- (methylene). The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

7. Y ２ When it is a single bond, L is one of the linking groups represented by the chemical formulas 2a to 2g above. The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

8. Y ２ is -O- or -O- (C １－４ In the case of alkylene, L is one of the linking groups represented by the chemical formulas 2h to 2k. The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

9. L is one linking group selected from the group shown below. The compound according to claim 1, or a pharmaceutically acceptable salt thereof. 【Transformation 3】 In the formula, Z and a are as defined in claim 1, * represents Y in the above chemical formula 1. ２ It means a point connected to [something].

10. Z is chloro, fluoro, methyl, or methoxy. The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

11. R ３ ha-CH ３ ien-CH=CH ２ ien-CH=CHCH ３ -C≡CH, or -C≡CCH ３ And, Here, R ３ It is either unsubstituted or chloro, fluoro, NH ２ NH (methyl) and N (methyl) ２ Substituted with one or two substituents selected from the group consisting of, The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

12. The compound represented by the aforementioned chemical formula 1 is represented by any one of the following chemical formulas 1-1 to 1-3: The compound according to claim 1, or a pharmaceutically acceptable salt thereof. 【Chemistry 4】 In chemical formulas 1-1 to 1-3, R' ２ is halogen, cyano, C １－４ Alkyl, C １－４ Haloalkyl, C １－４ Alkoxy, C １－４ Haloalkoxy, or -CONH(C) １－４ It is alkyl, Y １ , R １ , R ２ , Y ２ , L and R ３ This is as defined in claim 1.

13. The compound represented by the aforementioned chemical formula 1 is 1) 1-(4-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 2) 1-(4-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 3) 1-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2,5-dihydro-1H-pyrrole-1-yl)prop-2-en-1-one, 4) 1-(4-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 5) 1-(4-(1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 6) 1-(4-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 7) 1-(4-(1-(cyclobutylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 8) 1-(4-(6-((5-methylthiazole-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 9) 1-(4-(1-(cyclohexylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 10) 1-(4-(1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 11) 1-(4-(1-((4,4-difluorocyclohexyl)methyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 12) 1-(4-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 13) (S)-1-(4-(1-(sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 14) (R)-1-(4-(1-(sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 15) 1-(4-(1-benzyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 16) 1-(4-(6-((5-methylthiazole-2-yl)amino)-1-phenethyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 17) 1-(4-(6-((5-methylthiazole-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 18) 1-(4-(1-(3,3-dimethylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 19) 1-(4-(6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 20) 1-(4-(1-(2,2-difluorocyclopropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 21) 1-(4-(1-(difluoromethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 22) 2-(4-(1-acryloyl-1,2,3,6-tetrahydropyridine-4-yl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-1-yl)-2-methylpropanenitrile, 23) 2-(4-(1-acryloyl-1,2,5,6-tetrahydropyridine-3-yl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-1-yl)-2-methylpropanenitrile, 24) (R)-1-(4-(6-((5-methylthiazole-2-yl)amino)-1-(1,1,1-trifluoropropane-2-yl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 25) 1-(4-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3-methyl-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 26) 1-(4-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2,3,6,7-tetrahydro-1H-azepine-1-yl)prop-2-en-1-one, 27) 1-(7-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3-oxa-9-azabicyclo[3.3.1]non-6-en-9-yl)prop-2-en-1-one, 28) 1-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 29) 1-(3-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 30) 1-(3-(6-((5-methylthiazole-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 31) 1-(3-(1-(2,2-difluorocyclopropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 32) 1-(3-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 33) 1-(3-(1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 34) 1-(3-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 35) 1-(3-(6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 36) 1-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-9-azabicyclo[3.3.1]non-2-en-9-yl)prop-2-en-1-one, 37) 1-(3-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-9-azabicyclo[3.3.1]non-2-en-9-yl)prop-2-en-1-one, 38) 1-(3-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-9-azabicyclo[3.3.1]non-2-en-9-yl)prop-2-en-1-one, 39) 1-(3-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-8-azabicyclo[3.2.1]octo-2-en-8-yl)prop-2-en-1-one, 40) 1-(4-(6-((1H-imidazole-2-yl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 41) 1-(4-(1-isopropyl-6-((5-methyl-1,3,4-thiadiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 42) 1-(4-(1-isopropyl-6-((4-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 43) 1-(4-(1-isopropyl-6-(pyrimidine-4-ylamino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 44) 1-(4-(1-isopropyl-6-((6-methylpyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 45) 1-(4-(1-isopropyl-6-((6-(trifluoromethyl)pyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 46) 1-(4-(1-isopropyl-6-((6-methoxypyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 47) 1-(4-(6-((4-fluoropyridine-2-yl)amino)-1-isopropyl-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 48) 1-(4-(1-isopropyl-6-((4-(trifluoromethyl)pyridine-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 49) 1-(4-(1-isopropyl-6-((4-methylpyridine-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-3,6-dihydropyridine-1(2H)-yl)prop-2-en-1-one, 50) N-(3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 51) N-(2-fluoro-3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 52) N-(2-methoxy-3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 53) N-(3-methyl-5-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 54) N-(2-fluoro-5-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 55) N-(2-methyl-5-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 56) N-(2,6-dimethyl-3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 57) N-(2,6-difluoro-3-(1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 58) N-(3-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-methylphenyl)acrylamide, 59) N-(4-fluoro-3-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 60) N-(2,4-difluoro-5-(1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 61) N-(3-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-4-fluorophenyl)acrylamide, 62) N-(3-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-methylphenyl)acrylamide, 63) N-(4-fluoro-3-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 64) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-fluorophenyl)acrylamide, 65) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-methylphenyl)acrylamide, 66) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2,4-difluorophenyl)acrylamide, 67) N-(2,4-difluoro-5-(1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 68) (S)-N-(3-(1-(sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-4-fluorophenyl)acrylamide, 69) N-(5-(1-(3,3-dimethylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2,4-difluorophenyl)acrylamide, 70) N-(3-(1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-4-fluorophenyl)acrylamide, 71) N-(4-fluoro-3-(6-((5-methylthiazole-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 72) N-(2-fluoro-5-(6-((5-methylthiazole-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 73) N-(2-fluoro-3-(6-((5-methylthiazole-2-yl)amino)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 74) N-(5-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-methylphenyl)acrylamide, 75) N-(3-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-4-fluorophenyl)acrylamide, 76) N-(5-(1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)-2-fluorophenyl)acrylamide, 77) N-(2,4-difluoro-5-(6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 78) N-(4-fluoro-3-(6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)phenyl)acrylamide, 79) (S)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 80) 1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 81) (S)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 82) (R)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 83) 1-((3S,4R)-3-fluoro-4-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 84) (S)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 85) (S)-1-(2-(((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 86) (S)-1-(2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 87) 1-((2R,4S)-4-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 88) 1-((2S,4S)-4-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 89) (R)-1-(2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 90) (R)-1-(2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 91) 1-((3R,4R)-3-fluoro-4-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 92) Rac-1-((3S,4R)-3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-methylpyrrolidine-1-yl)prop-2-en-1-one, 93) (R)-1-(4,4-difluoro-2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 94) 1-((2R,4S)-2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)-4-methoxypyrrolidine-1-yl)prop-2-en-1-one, 95) (S)-1-(3-((1-isopropyl-6-((6-(trifluoromethyl)pyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 96) 1-((2R,4S)-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 97) (S)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrroridine-1-yl)prop-2-en-1-one, 98) 1-((2R,4S)-4-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 99) (S)-1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 100) 1-((2R,4S)-4-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 101) (S)-1-(3-((1-isopropyl-6-((6-methylpyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 102) (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 103) (S)-1-(3-((1-isopropyl-6-((6-methoxypyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 104) (S)-1-(3-((1-isobutyl-6-((6-methylpyrimidine-4-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 105) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 106) 1-((3R,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 107) 1-((3R,4S)-3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 108) 1-((3R,4R)-3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 109) 1-((3R,4S)-3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 110) 1-((3R,4R)-3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 111) 1-((S)-3-((1-((S)-sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 112) 1-((3R,4S)-3-((1-((S)-sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 113) 1-((3R,4R)-3-((1-((S)-sec-butyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 114) (S)-1-(3-((1-isopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 115) 1-((3R,4R)-3-fluoro-4-((1-isopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 116) 1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-methylpyrrolidine-1-yl)prop-2-en-1-one, 117) (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-(pyridine-2-ylmethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrroridine-1-yl)prop-2-en-1-one, 118) 1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 119) 1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 120) 1-((3R,4R)-3-fluoro-4-((6-((5-methylthiazole-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 121) (S)-1-(3-((1-benzyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 122) (S)-1-(3-((6-((5-ethylthiazole-2-yl)amino)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 123) 1-((3S)-3-((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 124) (S)-1-(3-((1-butyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 125) (S)-1-(3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 126) (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 127) (S)-1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 128) (S)-1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 129) (S)-1-(3-((1-(cyclohexylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 130) (S)-1-(3-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 131) 1-((3S,4R)-3-fluoro-4-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 132) 1-((3R,4S)-3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 133) (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 134) 1-((3S,4S)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 135) 1-((3R,4S)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 136) 1-(6-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-1-azaspiro[3,3]heptan-1-yl)prop-2-en-1-one, 137) 1-(6-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-1-azaspiro[3,3]heptan-1-yl)prop-2-en-1-one, 138) (S)-1-(3-((6-((5-fluoro-2-methylphenyl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 139) 1-((3S,4R)-3-fluoro-4-((6-((5-fluoro-2-methylphenyl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 140) (S)-1-(3-((1-(2-hydroxy-2-methylpropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 141) 1-((3S,4R)-3-fluoro-4-((1-(2-hydroxy-2-methylpropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 142) 1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 143) (R)-1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 144) (R)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 145) 1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 146) 1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 147) 1-((3S,4R)-3-fluoro-4-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 148) (S)-1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 149) (S)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 150) (S)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 151) (S)-1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 152) 1-((3R,4S)-3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 153) (S)-1-(3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 154) 1-((3R,4R)-3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 155) 1-(3-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 156) (R)-1-(3-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 157) 1-((3R,4R)-3-fluoro-4-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 158) (S)-1-(3-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 159) 1-((3S,4R)-3-fluoro-4-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 160) (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 161) 1-((3R,4R)-3-fluoro-4-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 162) (R)-1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 163) 1-(3-((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 164) 1-((2S,4S)-4-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 165) 1-(3-((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 166) 1-(3-methyl-3-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 167) 1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 168) 1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 169) (S)-1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 170) 1-((3R,4R)-3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 171) 1-((3S,4R)-3-fluoro-4-((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 172) 1-((3S)-3-((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)piperidine-1-yl)prop-2-en-1-one, 173) 1-((3R,4R)-3-fluoro-4-((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 174) 1-((3R,4R)-3-fluoro-4-((1-((R)-2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 175) 1-((3R,4R)-3-fluoro-4-((1-((S)-2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 176) 1-(3-methyl-3-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)azetidine-1-yl)prop-2-en-1-one, 177) 1-(3-((1-isopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 178) 1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-3-methylazetidine-1-yl)prop-2-en-1-one, 179) 1-((2S,4S)-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 180) 1-((2S,4S)-4-((1-(cyclopropylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 181) 2-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-6-yl)amino)thiazole-5-carbonitrile, 182) 2-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-6-yl)amino)-N-methylthiazole-5-carboxamide, 183) (S)-1-(3-((1-isopropyl-6-((4-methoxypyrimidine-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 184) (S)-1-(3-((1-isopropyl-6-((3-methoxypyrazine-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 185) 1-((2S,4S)-2-methyl-4-((1-methyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 186) 1-((2S,4S)-4-((1-ethyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 187) 1-((2S,4S)-2-methyl-4-((6-((5-methylthiazole-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 188) (S)-1-(3-((1-(2-fluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 189) 1-((3S,4R)-3-fluoro-4-((1-(2-fluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 190) (S)-1-(3-((1-(3-fluoropropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 191) 1-((3S,4R)-3-fluoro-4-((1-(3-fluoropropyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 192) (S)-1-(3-((6-((1H-pyrazole-3-yl)amino)-1-isopropyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 193) (S)-1-(3-((1-isopropyl-6-((1-methyl-1H-pyrazole-3-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 194) (S)-1-(3-((1-isopropyl-6-((5-methyl-1H-pyrazole-3-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 195) 1-((3R,4S)-3-((6-((1H-pyrazole-3-yl)amino)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 196) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methyl-1H-pyrazole-3-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 197) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((1-methyl-1H-pyrazole-3-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 198) (S)-3-((4-((1-acryloylpyrrolidine-3-yl)oxy)-1-isopropyl-1H-pyrrolo[3,2-c]pyridine-6-yl)amino)-1-methylpyridine-2(1H)-1-one, 199) 3-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-6-yl)amino)-1-methylpyridine-2(1H)-one, 200) 1-(2-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-5-azaspiro[3,4]octan-5-yl)prop-2-en-1-one, 201) 1-(7-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-1-azaspiro[4.4]nonan-1-yl)prop-2-en-1-one, 202) 1-(2-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-6-azaspiro[3,4]octan-6-yl)prop-2-en-1-one, 203) 1-(2-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-5-azaspiro[3.5]nonane-5-yl)prop-2-en-1-one, 204) 1-(7-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)-2-azaspiro[4.4]nonane-2-yl)prop-2-en-1-one, 205) (S)-1-(3-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 206) (S)-1-(3-((1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 207) (R)-1-(2-(((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 208) (R)-1-(2-(((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 209) (R)-1-(2-(((1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 210)(R)-1-(2-(((1-(2,2-difluoroethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 211) 1-((3S,4R)-3-fluoro-4-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 212) 1-((2R,4S)-2-methyl-4-((6-((5-methylthiazole-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 213) 1-((S)-3-((6-((5-methylthiazole-2-yl)amino)-1-((R)-1,1,1-trifluoropropan-2-yl)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 214) (R)-1-(3-(((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)piperidine-1-yl)prop-2-en-1-one, 215) (S)-1-(3-(((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)piperidine-1-yl)prop-2-en-1-one, 216) (S)-1-(3-(((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 217) 1-(2-(((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 218) 1-(2-(((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 219) (S)-1-(2-(((1-isopropyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 220) (S)-1-(2-(((1-(cyclopentylmethyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 221) 1-((2S)-2-(((1-(2-methylbutyl)-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 222) (S)-1-(2-(((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 223) (R)-1-(2-(((1-cyclopentyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)methyl)azetidine-1-yl)prop-2-en-1-one, 224) (S)-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 225) (S)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-in-1-one, 226) (S,E)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)buto-2-en-1-one, 227) (S,E)-4-(dimethylamino)-1-(3-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)buto-2-en-1-one, 228) N-(4-(((3R,4S)-4-fluoro-1-(vinylsulfonyl)pyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridine-6-yl)-5-methylthiazole-2-amine, 229) 2-Chloro-1-((3S,4R)-3-Fluoro-4-((1-Isobutyl-6-((5-Methylthiazole-2-yl)amino)-1H-Pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)ethane-1-one, 230) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)buto-2-in-1-one, and 231) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazole-2-yl)amino)-1H-pyrrolo[3,2-c]pyridine-4-yl)oxy)pyrrolidine-1-yl)prop-2-in-1-one It is one of the groups selected from the group consisting of The compound according to claim 1, or a pharmaceutically acceptable salt thereof.

14. A pharmaceutical composition comprising a compound according to any one of claims 1 to 13, or a pharmaceutically acceptable salt thereof, as an active ingredient.

15. A pharmaceutical composition for the prevention or treatment of inflammatory diseases, autoimmune diseases, or cancer, comprising a compound according to any one of claims 1 to 13, or a pharmaceutically acceptable salt thereof, as an active ingredient.

Images