Novel heterocyclic amine derivative and pharmaceutical composition comprising same

Abstract

The present invention relates to a novel heterocyclic amine derivative represented by the following Chemical Formula 1 and a pharmaceutical composition comprising the same. The compound according to the present invention is useful in the prevention or treatment of inflammatory diseases, autoimmune diseases or cancers. In Chemical Formula 1, Y1, R1, A, R2, k, Y2, L, X and R3 are as defined in the specification. [Chemical Formula 1]

Description

TECHNICAL FIELD

[0001] The present invention relates to novel heterocyclic amines useful as BTK (Bruton's tyrosine kinase) and ITK (Interleukin-2 tyrosine kinase) inhibitors and pharmaceutical compositions comprising the same. BACKGROUND

[0002] BTK (Bruton's tyrosine kinase) and ITK (Interleukin-2 tyrosine kinase) are a class of TEC (tyrosine kinases expressed in hepatocellular carcinoma) family kinases and act on various immune responses.

[0003] BTK acts as a regulator of early B cell development as well as activation, signaling and survival of mature B cells. B cells receive signals through the B cell receptor (BCR) which recognizes antigens attached to the surface of antigen presenting cells and is activated into mature antibody producing cells. However, abnormal signaling through the BCR leads to abnormal B cell proliferation and formation of pathogenic autoantibodies, which can induce cancer, autoimmune and / or inflammatory diseases. Therefore, in abnormal B cell proliferation, signaling through the BCR can be blocked when BTK is deficient. Therefore, inhibition of BTK can block B cell mediated disease processes, and thus, the use of BTK inhibitors is a useful method of treating B cell mediated diseases.

[0004] In addition, BTK can be expressed by other cells in addition to B cells that can 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 modulating diseases such as multiple sclerosis by modulating B cells and microglia cells (J. Kramer et al., Nature Reviews Neurology. 2023). In addition, monocytes from XLA patients in which BTK activity is absent show reduced TNF alpha production upon stimulation, and thus TNF alpha mediated inflammation can be inhibited by BTK inhibitors (see Horwood et al., J. Exp. Med. 197: 1603, 2003).

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

[0006] Accordingly, substances that inhibit BTK and ITK have been developed separately. As a BTK inhibitor, WO2008 / 039218 discloses 4-amino pyrazolo[3,4-d]pyrimidinyl piperidine derivatives, WO2015 / 061247 discloses heterocyclic compounds such as pyridine, pyrimidine, pyrazine, and pyridazine compounds, and WO2014 / 055934 discloses pyrimidinyl phenyl propenamide derivatives. In addition, as an ITK inhibitor, WO2005 / 066335 discloses amino benzimidazole derivatives, WO2005 / 056785 discloses pyridinone derivatives, WO2002 / 050071 discloses amino thiazole derivatives, and WO2014 / 036016 discloses benzimidazole derivatives.

[0007] Meanwhile, since autoimmune diseases such as multiple sclerosis are caused by complex factors of B cells and T cells (Kathrine E. Attfield et al., Nature Reviews Immunology. 2022. 734-750), simultaneously inhibiting B cells and T cells, rather than individually inhibiting only one of them, will be more effective in treating diseases.

[0008] However, since BTK acts on B cells as a kinase expressed on a B cell receptor subtype, and ITK acts on T cells as a kinase expressed on a T cell receptor subtype, BTK and ITK are different target substances from each other. Therefore, it is not possible to predict the ITK inhibitory effect of a BTK inhibitory substance, and thus it is not easy to develop a substance that double inhibits BTK and ITK.

[0009] In view of the above, as a result of research on new compounds, the present inventors have found compounds having excellent BTK and ITK dual activity inhibitory action, which have a different chemical structure from the BTK and ITK inhibitors reported to date, thereby completing the present application. The compounds belonging to the present application have BTK and ITK inhibitory activity as such, but do not exclude the possibility of exhibiting pharmacological action as an effective agent through a product of a special in vivo environment or metabolic process after being absorbed into the body. SUMMARY

[0010] PROBLEM TO BE SOLVED BY THE INVENTION An object of the present application is to provide a novel heterocyclic amine useful as a BTK and / or ITK inhibitor and a pharmaceutical composition comprising the same.

[0011] TECHNICAL SOLUTION To achieve the above object, according to the present application, there is provided a compound represented by the following Chemical Formula 1 or a pharmaceutically acceptable salt thereof: [Chemical Formula 1]

[0012] In Chemical Formula 1, Y1is a single bond, C 1-4 alkylene or C 1-4 haloalkylene, R1is C 1-10 alkyl, C 1-10 alkoxy, C 3-10 cycloalkyl, C 6-20 aryl, N-containing 6-membered heteroaryl, tetrahydrofuryl or tetrahydropyranyl, wherein R1is 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 5- or 6-membered heterocycle containing 1 to 3 heteroatoms selected from the group consisting of N, O and S, which is substituted with oxo (=O) or unsubstituted, provided that the 5- or 6-membered heterocycle contains at least one N, R2are each independently hydrogen, halogen, cyano, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 haloalkoxy or -CONH(C 1-4 alkyl), k is 1 or 2, Y2is a single bond, -O- or -O-(C 1-4 alkylene), L is any one of the linking groups represented by Chemical Formulae 2a to 2k,

[0013] in Chemical Formulae 2a to 2k, n is 0, 1, 2, or 3, Z is each independently halogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, or C 1-4 haloalkoxy, a is each independently 0, 1, or 2, L' is methylene, ethylene, or methylene-O-methylene, v and w are each independently 0, 1, or 2, with the proviso that v + w is an integer from 0 to 3, p to s are each independently 0, 1, 2, 3, or 4, with the proviso that p + q and r + s are each independently an integer from 2 to 4, * refers to the point of attachment to Y2in Chemical Formula 1 X is CO or SO2, and R3is C 1-4 alkyl, C 2-4 alkenyl, or C 2-4 alkynyl, wherein R3is unsubstituted, or substituted with one or more substituents selected from the group consisting of halogen, NH2, NH(C 1-4 alkyl), and N(C 1-4 alkyl)2.

[0014] Preferably, Y1may be a single bond, methylene, or ethylene.

[0015] Preferably, R1may be unsubstituted, or substituted with 1 to 3 substituents selected from the group consisting of halogen, cyano, hydroxy, C 1-4 alkyl, and C 1-4 haloalkyl.

[0016] More preferably, R1may be unsubstituted, or substituted with 1 to 3 substituents selected from the group consisting of chloro, fluoro, cyano, hydroxy, methyl, monofluoromethyl, difluoromethyl, and trifluoromethyl.

[0017] R1is, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, i-hexyl, n-octyl, i-octyl, n-nonyl, i-nonyl, n-decyl, i-decyl, methoxy, ethoxy, propoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyridyl, tetrahydrofuranyl or tetrahydropyranyl, wherein R1may be unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, hydroxy, C 1-4 alkyl and C 1-4 haloalkyl.

[0018] Further, for example, R1is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, i-hexyl, methoxy, ethoxy, propoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyridyl, tetrahydrofuranyl or tetrahydropyranyl, wherein R1may be unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, hydroxy, C

[0019] Further, preferably, when Y1is a single bond, R1is C 1-10 alkyl or C 3-10 cycloalkyl, wherein R1may be unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, hydroxy, C 1-4 alkyl and C 1-4 haloalkyl.

[0020] For example, when Y1is a single bond, R1is methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, n-hexyl, i-hexyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, wherein R1may be unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, hydroxy, C

[0021] Further, preferably, when Y1is C 1-4 alkylene or C 1-4 haloalkylene, R1is C 1-10 alkoxy, C 3-10 cycloalkyl, C 6-20 aryl, N-containing 6-membered heteroaryl, tetrahydrofuranyl or tetrahydropyranyl, wherein R1may be 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.

[0022] For example, when Y1is C 1-4 alkylene or C 1-4 haloalkylene, in particular, for example, when Y1is methylene or ethylene, R1is methoxy, ethoxy, propoxy, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, phenyl, pyridyl, tetrahydrofuranyl or tetrahydropyranyl, wherein R1may be unsubstituted, or substituted with one to three substituents selected from the group consisting of chloro, fluoro, cyano, hydroxy, methyl, monofluoromethyl, difluoromethyl and trifluoromethyl.

[0023] Preferably, A can be a benzene ring, a thiazole ring, a thiadiazole ring, an imidazole ring, a pyrazole ring, a pyrazine ring, a pyridine ring, a pyrimidine ring or a pyridin-2(lH)-one ring.

[0024] More preferably, may be represented by any one of the following Chemical Formulae A1 to A12:

[0025] In Chemical Formulae A1 to A12, R2is as defined in Chemical Formula 1.

[0026] Preferably, R2may each independently be hydrogen, chloro, fluoro, cyano, methyl, ethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxy or -CONH(methyl).

[0027] Meanwhile, k refers to the number of R2, and when k is 2, the two R2may be the same as or different from each other.

[0028] More preferably, A is a benzene ring, a thiazole ring, a thiadiazole ring, a pyrazine ring, a pyridine ring or a pyridin-2(lH)-one ring, and R2is each independently halogen, cyano, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy, C 1-4 haloalkoxy or -CONH(methyl); or A is an imidazole ring, and R2is hydrogen; or A is a pyrazole ring or a pyrimidine ring, and R2is each independently hydrogen, halogen, C 1-4 alkyl, C 1-4 haloalkyl, C 1-4 alkoxy or C 1-4 haloalkoxy.

[0029] Preferably, Y2may be a single bond, -O-, or -O-(methylene).

[0030] wherein, when Y2is -O-(methylene), the (methylene) can be attached to L.

[0031] Preferably, when Y2is a single bond, L can be any one of the linking groups represented by Chemical Formulae 2a to 2g.

[0032] For example, when Y2is a single bond, L can be any one of the linking groups represented by Chemical Formulae 2a, 2b, 2c, 2e, 2f, and 2g.

[0033] Further, preferably, when Y2is -O- or -O-(C 1-4 alkylene), L can be any one of the linking groups represented by Chemical Formulae 2h to 2k.

[0034] For example, when Y2is -O-, L can be a linking group represented by Chemical Formula 2i or 2k.

[0035] Further, for example, when Y2is -O-(C 1-4 alkylene), L can be a linking group represented by Chemical Formula 2h or 2i.

[0036] Meanwhile, a refers to the number of Z, and when a is 2, the two Zs can be the same as or different from each other.

[0037] Preferably, L can be any one of the linking groups represented by Chemical Formulae 2a, 2b, 2c, 2e, 2f, 2g, 2h, 2i, and 2k.

[0038] For example, in Chemical Formula 2a, n can be 2, and a can be 0.

[0039] Further, for example, in Chemical Formula 2b, n can be 1 or 2, and a can be 0 or 1.

[0040] Further, for example, in Chemical Formula 2c, L' can be methylene-O-methylene, and a can be 0.

[0041] Further, for example, in Chemical Formula 2e, v and w can each be 1, and a can be 0.

[0042] Further, for example, in Chemical Formula 2f, v and w can each be 1; or v can be 1, w can be 2, and a can be 0.

[0043] Further, for example, in Chemical Formula 2g, a can be 0, 1, or 2.

[0044] Further, for example, in Chemical Formula 2h, n can be 0, 1, or 2, and a can be 0, 1, or 2.

[0045] Further, for example, in Chemical Formula 2i, n can be 0, 1 or 2, and a can be 0, 1 or 2.

[0046] Further, for example, in Chemical Formula 2k, p and q can each independently be 1 or 2, r can be 0 or 1, and s can be 2, 3 or 4.

[0047] In this regard, p+q is 2 or 3, and r+s is 2, 3 or 4.

[0048] Further, preferably, L can be any linker selected from the group represented by:

[0049] wherein, Z and a are as defined in Chemical Formula 1, and * refers to the point of attachment to Y2in Chemical Formula 1.

[0050] Preferably, **-Y2-L- can be any of the linkers represented by Chemical Formulae 3a to 3r:

[0051] In Chemical Formulae 3a to 3r, m is 0 or 1, Z and a are as defined in Chemical Formula 1, and ** refers to the point of attachment to the 4thcarbon of the pyrrolo[3,2-c]pyridine ring in Chemical Formula 1.

[0052] Further, for example, when Y2is -O-, the compound can be a stereoisomer represented by the following Chemical Formula 1A or 1B, or a mixture thereof: [Chemical Formula 1A]

[0053] [Chemical Formula 1B]

[0054] In Chemical Formulae 1A and 1B, Y1, R1, A, R2, k, L, X and R3are as defined in Chemical Formula 1.

[0055] Further, for example, when Y2is -O-(methylene), the compound can be a stereoisomer represented by the following Chemical Formula 1C or 1D, or a mixture thereof: [Chemical Formula 1C]

[0056] [Chemical Formula 1D]

[0057] In Chemical Formulae 1C and 1D, Y1, R1, A, R2, k, L, X, and R3 are as defined in Chemical Formula 1.

[0058] Preferably, Z can be chlorine, fluorine, methyl, or methoxy.

[0059] Preferably, R3 can be unsubstituted, or substituted with 1 or 2 substituents selected from the group consisting of chlorine, fluorine, NH2, NH(methyl), and N(methyl)2.

[0060] More preferably, R3 can be -CH3, -CH=CH2, -CH=CHCH3, -C≡CH, or -C≡CCH3, wherein R3 can be unsubstituted, or substituted with 1 or 2 substituents selected from the group consisting of chlorine, fluorine, NH2, NH(methyl), and N(methyl)2.

[0061] For example, R3 can be -CH3, -CH2Cl, -CH=CH2, -CF=CH2, -CH=CHCH3, -CH=CHCH2N(CH3)2, -C≡CH, or -C≡CCH3.

[0062] Meanwhile, the compound represented by Chemical Formula 1 can be represented by any one of the following Chemical Formulae 1-1 to 1-3: [Chemical Formula 1-1]

[0063] [Chemical Formula 1-2]

[0064] [Chemical Formula 1-3]

[0065] In Chemical Formulae 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 alkyl), Y1, R1, A, R2, Y2, L, and R3 are as defined in Chemical Formula 1.

[0066] For example, R'2 can be chlorine, fluorine, cyano, methyl, ethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxy, or -CONH(methyl).

[0067] Preferably, in Chemical Formula 1-1, A is a thiazole ring, a thiadiazole ring, an imidazole ring, a pyrazole ring, a pyrazine ring, a pyridine ring, a pyrimidine ring, or a pyridin-2(lH)-one ring, and L is any one of the linking groups represented by Chemical Formulae 2a, 2b, 2c, 2e, 2f, 2g, 2h, 2i, and 2k.

[0068] Preferably, in Chemical Formula 1-2, A is a benzene ring, and L is a linking group represented by Chemical Formula 2i.

[0069] Preferably, in Chemical Formula 1-3, A is a thiazole ring, and L is a linking group represented by Chemical Formula 2i.

[0070] Preferably, A is Chemical Formula A1, R2 is halogen, cyano, C 1-4 alkyl, C 1-4 haloalkyl, or -CONH(C 1-4 alkyl), Y2 is a single bond, -O-, or -O-(C 1-4 alkylene), and L is any one of the linking groups represented by Chemical Formulae 2a to 2c and 2e to 2k.

[0071] Preferably, A is Chemical Formula A2, R2 is C 1-4 alkyl, or C 1-4 haloalkyl, Y2 is a single bond, and L is a linking group represented by Chemical Formula 2b.

[0072] Preferably, A is Chemical Formula A3, R2 is hydrogen, Y2 is a single bond, and L is a linking group represented by Chemical Formula 2b.

[0073] Preferably, A is Chemical Formula A4, R2 is C 1-4 alkyl, or C 1-4 haloalkyl, Y2 is a single bond, and L is a linking group represented by Chemical Formula 2b.

[0074] 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 C1-4 Halogenated alkoxy groups, Y2 is -O-, and L is a linker represented by the chemical formula 2i.

[0075] Preferably, A is the chemical formula A7. R2 is a halogen, C 1-4 Alkyl or C 1-4 Halogenated alkyl groups, Y2 is a single bond, and L is a linker represented by the chemical formula 2b.

[0076] Preferably, A is the chemical formula A8. R2 is hydrogen, halogen, or C. 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy or C 1-4 Halogenated alkoxy groups, Y2 is a single bond or -O-, and L is a linker represented by the chemical formula 2b or 2i.

[0077] Preferably, A is the chemical formula A9. R2 is hydrogen, halogen, or C. 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy or C 1-4 Halogenated alkoxy groups, Y2 is -O-, and L is a linker represented by the chemical formula 2i.

[0078] Preferably, A is chemical formula A10. R2 is C 1-4 Alkoxy or C 1-4 Halogenated alkoxy groups, Y2 is -O-, and L is a linker represented by the chemical formula 2i.

[0079] Preferably, A is chemical formula Al11. R2 is C 1-4 Alkyl or C 1-4 Halogenated alkyl groups, Y2 is -O-, and L is a linker represented by the chemical formula 2i.

[0080] Preferably, A is chemical formula Al2. R2 is independently a halogen, C 1-4 Alkyl or C 1-4 Halogenated alkyl groups, Y2 is -O-, and L is a linker represented by Chemical Formula 2i.

[0081] Meanwhile, representative examples of the compound represented by Chemical Formula 1 are as follows: 1) 1-(4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6- dihydropyridin-1(2H)-yl)prop-2-en-1-one, 2) 1-(4-(1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6- dihydropyridin-1(2H)-yl)prop-2-en-1-one, 3) 1-(3-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2,5- dihydropyrrol-1-yl)prop-2-en-1-one, 4) 1-(4-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 5) 1-(4-(1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6- dihydropyridin-1(2H)-yl)prop-2-en-1-one, 6) 1-(4-(1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6- dihydropyridin-1(2H)-yl)prop-2-en-1-one, 7) 1-(4-(1-(cyclobutylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 8) 1-(4-(6-((5-methylthiazol-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2- c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 9) 1-(4-(1-(cyclohexylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 10) 1-(4-(1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 11) 1-(4-(1-((4,4-difluorocyclohexyl)methyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 12) 1-(4-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 13)(S)-1-(4-(1-(sec-butyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 14)(R)-1-(4-(1-(sec-butyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 15) 1-(4-(1-benzyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 16) 1-(4-(6-((5-methylthiazol-2-yl)amino)-1-phenethyl-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 17) 1-(4-(6-((5-methylthiazol-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 18) 1-(4-(1-(3,3-dimethylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 19) 1-(4-(6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2- c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 20) 1-(4-(1-(2,2-difluorocyclopropyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 21) 1-(4-(1-(difluoromethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 22) 2-(4-(1-acryloyl-1,2,3,6-tetrahydropyridin-4-yl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropanenitrile, 23) 2-(4-(1-acryloyl-1,2,5,6-tetrahydropyridin-3-yl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropanenitrile, 24) (R)-1-(4-(6-((5-methylthiazol-2-yl)amino)-1-(1,1,1-trifluoropropan-2-yl)-1H-pyrrolo[3,2- c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 25) 1-(4-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)-3-methyl-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 26) 1-(4-(1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2,3,6,7- tetrahydro-1H-azepin-1-yl)prop-2-en-1-one, 27) 1-(7-(1-isopropyl-6-((5-methylthiazol-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-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8- azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 29) 1-(3-(1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8- azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 30) 1-(3-(6-((5-methylthiazol-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H- pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 31) 1-(3-(1-(2,2-difluorocyclopropyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 32) 1-(3-(1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8- azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 33) 1-(3-(1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8- azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 34) 1-(3-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 35) 1-(3-(6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4- yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 36) 1-(3-(1-methyl-6-((5-methylthiazol-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-methylthiazolyl-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-methylthiazolyl-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-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 40) 1-(4-(6-((1H-imidazol-2-yl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 41) 1-(4-(1-isopropyl-6-((5-methyl-1,3,4-thiadiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 42) 1-(4-(1-isopropyl-6-((4-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 43) 1-(4-(1-isopropyl-6-(pyrimidin-4-ylamino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 44) 1-(4-(1-isopropyl-6-((6-methylpyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 45) 1-(4-(1-isopropyl-6-((6-(trifluoromethyl)pyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 46) 1-(4-(1-isopropyl-6-((6-methoxypyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 47) 1 -(4-(6-((4-fluoropyridin-2-yl)amino)- 1 -isopropyl- 1 H-pyrrolo[3,2-c]pyridin-4-yl)- 3,6-dihydropyridin-l(2H)-yl)prop-2-en-l-one, 48) 1 -(4-( 1 -isopropyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)- 1 H-pyrrolo[3,2- c]pyridin-4-yl)-3,6-dihydropyridin-l(2H)-yl)prop-2-en-l-one, 49) 1 -(4-( 1 -isopropyl-6-((4-methylpyridin-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin-4-yl)- 3,6-dihydropyridin-l(2H)-yl)prop-2-en-l-one, 50) N-(3-( 1 -methyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 51) N-(2-fluoro-3-( 1 -methyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin- 4-yl)phenyl)acrylamide, 52) N-(2-methoxy-3-( 1 -methyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin- 4-yl)phenyl)acrylamide, 53) N-(3-methyl-5-( 1 -methyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin- 4-yl)phenyl)acrylamide, 54) N-(2-fluoro-5-( 1 -methyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin- 4-yl)phenyl)acrylamide, 55) N-(2-methyl-5-( 1 -methyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin- 4-yl)phenyl)acrylamide, 56) N-(2,6-dimethyl-3-( 1 -methyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin- 4-yl)phenyl)acrylamide, 57) N-(2,6-difluoro-3-( 1 -methyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin- 4-yl)phenyl)acrylamide, 58) N-(3-( 1 -isopropyl-6-((5-methylthiazol-2-yl)amino)- 1 H-pyrrolo[3,2-c]pyridin-4-yl)- 2-methylphenyl)acrylamide, 59) N-(4-fluoro-3-(1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)phenyl)acrylamide, 60) N-(2,4-difluoro-5-(1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)phenyl)acrylamide, 61) N-(3-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-4-fluorophenyl)acrylamide, 62) N-(3-(1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)-2-methylphenyl)acrylamide, 63) N-(4-fluoro-3-(1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)phenyl)acrylamide, 64) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-2-fluorophenyl)acrylamide, 65) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-2-methylphenyl)acrylamide, 66) N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-2,4-difluorophenyl)acrylamide, 67) N-(2,4-difluoro-5-(1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)phenyl)acrylamide, 68) (S)-N-(3-(1-(sec-butyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-4-fluorophenyl)acrylamide, 69) N-(5-(1-(3,3-dimethylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-2,4-difluorophenyl)acrylamide, 70) N-(3-(1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-4-fluorophenyl)acrylamide, 71) N-(4-fluoro-3-(6-((5-methylthiazol-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)- 1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 72) N-(2-fluoro-5-(6-((5-methylthiazol-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)- 1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 73) N-(2-fluoro-3-(6-((5-methylthiazol-2-yl)amino)-1-((tetrahydro-2H-pyran-4-yl)methyl)- 1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 74) N-(5-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-2-methylphenyl)acrylamide, 75) N-(3-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-4-fluorophenyl)acrylamide, 76) N-(5-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)-2-fluorophenyl)acrylamide, 77) N-(2,4-difluoro-5-(6-((5-methylthiazol-2-yl)amino)-1-(2,2,2- trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 78) N-(4-fluoro-3-(6-((5-methylthiazol-2-yl)amino)-1-(2,2,2- trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 79) (S)-1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 80) 1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)azetidin-1-yl)prop-2-en-1-one, 81) (S)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 82) (R)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 83) 1-((3S,4R)-3-fluoro-4-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 84) (S)-1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 85) (S)-1-(2-(((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 86) (S)-1-(2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)azetidin-1-yl)prop-2-en-1-one, 87) 1-((2R,4S)-4-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 88) 1-((2S,4S)-4-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 89) (R)-1-(2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 90) (R)-1-(2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)azetidin-1-yl)prop-2-en-1-one, 91) 1-((3R,4R)-3-fluoro-4-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 92) rac-1-((3S,4R)-3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-4-methylpyrrolidin-1-yl)prop-2-en-1-one, 93) (R)-1-(4,4-difluoro-2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 94) 1-((2R,4S)-2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)-4-methoxypyrrolidin-1-yl)prop-2-en-1-one, 95) (S)-1-(3-((1-isopropyl-6-((6-(trifluoromethyl)pyrimidin-4-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 96) 1-((2R,4S)-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 97) (S)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 98) 1-((2R,4S)-4-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 99) (S)-1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 100) 1-((2R,4S)-4-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 101) (S)-1-(3-((1-isopropyl-6-((6-methylpyrimidin-4-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 102) (S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 103) (S)-1-(3-((1-isopropyl-6-((6-methoxy-pyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 104) (S)-1-(3-((1-isobutyl-6-((6-methyl-pyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 105) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 106) 1-((3R,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 107) 1-((3R,4S)-3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 108) 1-((3R,4R)-3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 109) 1-((3R,4S)-3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 110) 1-((3R,4R)-3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 111) 1-((S)-3-((1-((S)-sec-butyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 112) 1-((3R,4S)-3-((1-((S)-sec-butyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 113) 1-((3R,4R)-3-((1-((S)-sec-butyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 114) (S)-1-(3-((1-isopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 115) 1-((3R,4R)-3-fluoro-4-((1-isopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 116) 1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)- 4-methylpyrrolidin-1-yl)prop-2-en-1-one, 117) (S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-(pyridin-2-ylmethyl)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 118) 1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy) azetidin-1-yl)prop-2-en-1-one, 119) 1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)- 3-methylazetidin-1-yl)prop-2-en-1-one, 120) 1-((3R,4R)-3-fluoro-4-((6-((5-methylthiazol-2-yl)amino)-1-((1-(trifluoromethyl) cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1- one, 121) (S)-1-(3-((1-benzyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 122) (S)-1-(3-((6-((5-ethylthiazol-2-yl)amino)-1-isobutyl-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 123) 1-((3S)-3-((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 124) (S)-1-(3-((1-butyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 125) (S)-1-(3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 126) (S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 127) (S)-1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 128) (S)-1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 129) (S)-1-(3-((1-(cyclohexylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 130) (S)-1-(3-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 131) 1-((3S,4R)-3-fluoro-4-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 132) 1-((3R,4S)-3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 133) (S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 134) 1-((3S,4S)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 135) 1-((3R,4S)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 136) 1-(6-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-1- azaspiro[3.3]heptan-1-yl)prop-2-en-1-one, 137) 1-(6-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-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]pyridin-4- yl)oxy)pyrrolidin-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]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 140) (S)-1-(3-((1-(2-hydroxy-2-methylpropyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 141) 1-((3S,4R)-3-fluoro-4-((1-(2-hydroxy-2-methylpropyl)-6-((5-methylthiazol-2-yl)amino)- 1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 142) 1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)azetidin-1-yl)prop-2-en-1-one, 143) (R)-1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 144) (R)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 145) 1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)azetidin-1-yl)prop-2-en-1-one, 146) 1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)azetidin-1-yl)prop-2-en-1-one, 147) 1-((3S,4R)-3-fluoro-4-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 148) (S)-1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 149) (S)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 150) (S)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 151) (S)-1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 152) 1-((3R,4S)-3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 153) (S)-1-(3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 154) 1-((3R,4R)-3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 155) 1-(3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-3-methylazetidin-1-yl)prop-2-en-1-one, 156) (R)-1-(3-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 157) 1-((3R,4R)-3-fluoro-4-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 158) (S)-1-(3-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 159) 1-((3S,4R)-3-fluoro-4-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 160) (S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)piperidin-1-yl)prop-2-en-1-one, 161) 1-((3R,4R)-3-fluoro-4-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 162) (R)-1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 163) 1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)-3-methylazetidin-1-yl)prop-2-en-1-one, 164) 1-((2S,4S)-4-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 165) 1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)-3-methylazetidin-1-yl)prop-2-en-1-one, 166) 1-(3-methyl-3-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin- 4-yl)oxy)azetidin-1-yl)prop-2-en-1-one, 167) 1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-3-methylazetidin-1-yl)prop-2-en-1-one, 168) 1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin- 4-yl)oxy)-3-methylazetidin-1-yl)prop-2-en-1-one, 169) (S)-1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 170) 1-((3R,4R)-3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 171) 1-((3S,4R)-3-fluoro-4-((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 172) 1-((3S)-3-((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 173) 1-((3R,4R)-3-fluoro-4-((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 174) 1-((3R,4R)-3-fluoro-4-((1-((R)-2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)- 1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 175) 1-((3R,4R)-3-fluoro-4-((1-((S)-2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)- 1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 176) 1-(3-methyl-3-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)azetidin-1-yl)prop-2-en-1-one, 177) 1-(3-((1-isopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)-3-methylazetidin-1-yl)prop-2-en-1-one, 178) 1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-3-methylazetidin-1-yl)prop-2-en-1-one, 179) 1-((2S,4S)-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 180) 1-((2S,4S)-4-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 181) 2-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidin-3-yl)oxy)-1-isobutyl-1H- pyrrolo[3,2-c]pyridin-6-yl)amino)thiazole-5-carbonitrile, 182) 2-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidin-3-yl)oxy)-1-isobutyl-1H- pyrrolo[3,2-c]pyridin-6-yl)amino)-N-methylthiazole-5-carboxamide, 183) (S)-1-(3-((1-isopropyl-6-((4-methoxyprimidin-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 184) (S)-1-(3-((1-isopropyl-6-((3-methoxyprimidin-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 185) 1-((2S,4S)-2-methyl-4-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 186) 1-((2S,4S)-4-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-methylpyrrolidin-1-yl)prop-2-en-1-one, 187) 1-((2S,4S)-2-methyl-4-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 188) (S)-1-(3-((1-(2-fluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 189) 1-((3S,4R)-3-fluoro-4-((1-(2-fluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 190) (S)-1-(3-((1-(3-fluoropropyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 191) 1-((3S,4R)-3-fluoro-4-((1-(3-fluoropropyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 192) (S)-1-(3-((6-((1H-pyrazol-3-yl)amino)-1-isopropyl-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 193) (S)-1-(3-((1-isopropyl-6-((1-methyl-1H-pyrazol-3-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 194) (S)-1-(3-((1-isopropyl-6-((5-methyl-1H-pyrazol-3-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 195) 1-((3R,4S)-3-((6-((1H-pyrazol-3-yl)amino)-1-isobutyl-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 196) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methyl-1H-pyrazol-3-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 197) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((1-methyl-1H-pyrazol-3-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 198) (S)-3-((4-((1-acryloylpyrrolidin-3-yl)oxy)-1-isopropyl-1H-pyrrolo[3,2-c]pyridin-6- yl)amino)-1-methylpyridin-2(1H)-one, 199) 3-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidin-3-yl)oxy)-1-isobutyl-1H- pyrrolo[3,2-c]pyridin-6-yl)amino)-1-methylpyridin-2(1H)-one, 200) 1-(2-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-5-azaspiro[3.4]octan-5-yl)prop-2-en-1-one, 201) 1-(7-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-1-azaspiro[4.4]nonan-1-yl)prop-2-en-1-one, 202) 1-(2-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-6-azaspiro[3.4]octan-6-yl)prop-2-en-1-one, 203) 1-(2-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-5-azaspiro[3.5]nonan-5-yl)prop-2-en-1-one, 204) 1-(7-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)-2-azaspiro[4.4]nonan-2-yl)prop-2-en-1-one, 205) (S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2- trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 206) (S)-1-(3-((1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 207) (R)-1-(2-(((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2- trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 208) (R)-1-(2-(((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)azetidin-1-yl)prop-2-en-1-one, 209) (R)-1-(2-(((1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)azetidin-1-yl)prop-2-en-1-one, 210) (R)-1-(2-(((1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 211) 1-((3S,4R)-3-fluoro-4-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2- trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 212) 1-((2R,4S)-2-methyl-4-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2- trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 213) 1-((S)-3-((6-((5-methylthiazol-2-yl)amino)-1-((R)-1,1,1-trifluoropropan-2-yl)- 1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 214) (R)-1-(3-(((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)piperidin-1-yl)prop-2-en-1-one, 215) (S)-1-(3-(((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)piperidin-1-yl)prop-2-en-1-one, 216) (S)-1-(3-(((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 217) 1-(2-(((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 218) 1-(2-(((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)methyl)azetidin-1-yl)prop-2-en-1-one, 219) (S)-1-(2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 220) (S)-1-(2-(((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 221) 1-((2S)-2-(((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 222) (S)-1-(2-(((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 223) (R)-1-(2-(((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)methyl)azetidin-1-yl)prop-2-en-1-one, 224) (S)-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 225) (S)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)prop-2-yn-1-one, 226) (S,E)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4- yl)oxy)pyrrolidin-1-yl)but-2-en-1-one, 227) (S,E)-4-(dimethylamino)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)but-2-en-1-one, 228) N-(4-(((3R,4S)-4-fluoro-1-(vinylsulfonyl)pyrrolidin-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-5-methylthiazol-2-amine, 229) 2-chloro-1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)ethan-1-one, 230) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)but-2-yn-1-one, and 231) 1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-yn-1-one.

[0082] Meanwhile, the compounds represented by Chemical Formula 1 can be understood to include the concept of all possible stereoisomers, mixtures of stereoisomers, and isotopic derivatives of the compounds.

[0083] Specifically, when the compounds contain one or more stereocenters, the "stereoisomers" of the compounds can be understood to include all possible diastereomeric and enantiomeric configurations.

[0084] Further, the "isotopic derivatives" of the compounds mean that one or more atoms in the compounds are replaced by naturally occurring or non-naturally occurring isotopes. For example, the isotopic derivatives of the compounds include compounds in which at least one hydrogen in the compounds is replaced by deuterium.

[0085] In addition, the compounds of the present disclosure can exist in the form of a salt, particularly a pharmaceutically acceptable salt. As the salt, an acid addition salt formed from a pharmaceutically acceptable free acid can be used without limitation, which is commonly used in the art. The term "pharmaceutically acceptable salt" used herein means any organic or inorganic addition salt of the compounds represented by Chemical Formula 1, which is relatively non-toxic and harmless to the patient, and is effective to activate, and whose side effects do not reduce the beneficial effects of the above-mentioned compounds.

[0086] As the free acid, organic acids and inorganic acids can be used. Examples of the inorganic acid include hydrochloric acid, phosphoric acid, sulfuric acid, nitric acid, tartaric acid, and the like. Examples of the organic acid include 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, carbonic acid, vanillic acid, hydroiodic acid, and the like, but are not limited thereto. Preferably, the salt can be a hydrochloride.

[0087] Further, the pharmaceutically acceptable metal salt can be obtained by a conventional method using a base. For example, the compound represented by Chemical Formula 1 is dissolved in an excess of an alkali metal hydroxide solution or an alkaline earth metal hydroxide solution, the insoluble salt is filtered, and the filtrate is evaporated and dried to obtain the pharmaceutically acceptable metal salt. At this time, it is particularly preferable to prepare a sodium salt, a potassium salt, or a calcium salt as the metal salt.

[0088] When preparing the compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt or solvate thereof, a pharmaceutically unacceptable salt or solvate of the compound represented by Chemical Formula 1 can be used as an intermediate.

[0089] Further, the compound represented by Chemical Formula 1 according to the present application includes not only a pharmaceutically acceptable salt thereof, but also a solvate such as a hydrate thereof, or a prodrug thereof, but is not limited thereto.

[0090] The solvate of the compound represented by Chemical Formula 1 can be prepared from the compound represented by Chemical Formula 1 using a general method known in the art.

[0091] Further, unless otherwise specified, the "prodrug" of the compound can be understood to mean all derivatives of the compound which can be hydrolyzed, oxidized, or otherwise reacted under biological conditions (in vitro or in vivo) to provide the compound of the present application, a stereoisomer thereof, a mixture of stereoisomers thereof, an isotopic derivative thereof, or a pharmaceutically acceptable salt thereof.

[0092] Further, in the present application, the compound represented by Chemical Formula 1 can include not only a stoichiometric hydrate, but also a compound containing water in various amounts. The solvate of the compound represented by Chemical Formula 1 according to the present application includes a stoichiometric solvate and a non-stoichiometric solvate.

[0093] Further, for example, when L is any one of the linkers represented by Chemical Formulas 2a to 2f, the compound represented by Chemical Formula 1 can be prepared by the following Reaction Scheme 1.

[0094] [Reaction Scheme 1]

[0095] In Reaction Scheme 1, P1 refers to a protecting group, and the remaining substituents are as defined in Chemical Formula 1.

[0096] For example, P1 can be any one protecting group selected from the group consisting of tert-butyloxycarbonyl (Boc), benzyloxycarbonyl (Cbz), p-methoxybenzyl carbonyl (Moz), 9-fluorenylmethyloxycarbonyl (Fmoc), acetyl (Ac), benzoyl (Bz), benzyl (Bn), and p-methoxybenzyl (PMB).

[0097] Step 1-1 is a step of reacting a compound represented by Chemical Formula 1-1 with a compound represented by Chemical Formula 1-2 to prepare a compound represented by Chemical Formula 1-3. The above reaction is a Suzuki coupling reaction, which is preferably performed in the presence of a palladium catalyst and a base.

[0098] Step 1-2 is a step of reacting a compound represented by Chemical Formula 1-3 with a compound represented by Chemical Formula 1-4 to prepare a compound represented by Chemical Formula 1-5. The above reaction is an amine substitution reaction, which is preferably performed in the presence of a palladium catalyst and a base.

[0099] Step 1-3 is a step of removing a protecting group from a compound represented by Chemical Formula 1-5, and then reacting with a compound represented by Chemical Formula 1-6 or 1-7 to prepare a compound represented by Chemical Formula 1. The removal of the protecting group is preferably performed under acidic conditions 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, which is preferably performed in the presence of a base.

[0100] Further, for example, when L is a linker represented by Chemical Formula 2g, a compound represented by Chemical Formula 1 can be prepared by the following Reaction Scheme 2.

[0101] [Reaction Scheme 2]

[0102] In Reaction Scheme 2, P1 refers to a protecting group and is as defined in Reaction Scheme 1, and the remaining substituents are as defined in Chemical Formula 1.

[0103] Step 2-1 is a step of reacting a compound represented by Chemical Formula 1-1 with a compound represented by Chemical Formula 1-8 to prepare a compound represented by Chemical Formula 1-3, and can be performed in the same manner as Step 1-1 of Reaction Scheme 1, except that the reaction groups for the Suzuki coupling reaction are different.

[0104] Further, Steps 2-2 and 2-3 can be performed in the same manner as Steps 1-2 and 1-3 of Reaction Scheme 1, respectively.

[0105] Further, for example, when L is any one of the linking groups represented by Chemical Formulae 2h to 2j, the compound represented by Chemical Formula 1 can be prepared by the following Reaction Scheme 3.

[0106] [Reaction Scheme 3]

[0107] In Reaction Scheme 3, P1 refers to a protecting group and is as defined in Reaction Scheme 1, and the remaining substituents are as defined in Chemical Formula 1.

[0108] Step 3-1 is a step of reacting a compound represented by Chemical Formula 1-1 with a compound represented by Chemical Formula 1-9 to prepare a compound represented by Chemical Formula 1-3. The above reaction is a nucleophilic substitution reaction, which is preferably performed in the presence of a base.

[0109] Further, Steps 3-2 and 3-3 can be performed in the same manner as Steps 1-2 and 1-3 of Reaction Scheme 1, respectively.

[0110] The preparation method of each of the above steps can be described in more detail in the following Examples.

[0111] According to another embodiment of the present application, there is provided a pharmaceutical composition comprising a compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.

[0112] More specifically, the present application can be understood to provide a pharmaceutical composition comprising a compound represented by Chemical Formula 1, a stereoisomer thereof, a mixture of stereoisomers thereof, an isotopic derivative thereof, a pharmaceutically acceptable salt thereof, or a prodrug thereof as an active ingredient.

[0113] According to still another embodiment of the present application, there is provided a pharmaceutical composition for preventing or treating an inflammatory disease, an autoimmune disease, or cancer, which comprises a compound represented by Chemical Formula 1 or a pharmaceutically acceptable salt thereof as an active ingredient.

[0114] More specifically, the present application can be understood to provide a pharmaceutical composition for preventing or treating an inflammatory disease, an autoimmune disease, or cancer, which is associated with ITK and BTK inhibitory action, which comprises a compound represented by Chemical Formula 1, a stereoisomer thereof, a mixture of stereoisomers thereof, an isotopic derivative thereof, a pharmaceutically acceptable salt thereof, or a prodrug thereof as an active ingredient.

[0115] In this case, the autoimmune diseases include rheumatoid arthritis, systemic lupus erythematosus, juvenile diabetes, psoriasis, aphthous stomatitis, chronic thyroiditis, some idiopathic aplastic anemia, primary sclerosing, ulcerative colitis, Behcet's disease, Crohn's disease, silicosis, asbestosis, Sjogren's syndrome, Guillain-Barre syndrome, dermatomyositis, polymyositis, multiple sclerosis, anti-MOG antibody disease, autoimmune hemolytic anemia, autoimmune encephalomyelitis, myasthenia gravis, Graves' thyroid hyperplasia, nodular multiple arteritis, ankylosing spondylitis, fibrositis, temporal arteritis, Wilson's disease, asthma, optic neuritis, Fanconi syndrome, or degenerative neurological diseases such as Alzheimer's disease, Parkinson's disease, Lou Gehrig's disease, and the like.

[0116] The cancer includes blood cancer, extranodal marginal zone B-cell lymphoma, glioblastoma, lymphoplasmacytic lymphoma, acute myeloid leukemia, macroglobulinemia, B-cell lymphoma, chronic lymphocytic leukemia, follicular lymphoma, non-Hodgkin's lymphoma, diffuse large B-cell lymphoma, hairy cell leukemia, mantle cell lymphoma, glioblastoma, bladder cancer, pancreatic cancer, ovarian cancer, colorectal cancer, kidney cancer, stomach cancer, transitional cell carcinoma, carcinoid tumor, breast cancer, non-small cell lung cancer, or multiple myeloma.

[0117] As used herein, the term "prevention" refers to any act of delaying or inhibiting the occurrence, spread, or recurrence of the above-mentioned diseases by administering the composition of the present application, and "treatment" refers to any act of better improving or changing the symptoms of the above-mentioned diseases by administering the composition of the present application.

[0118] The pharmaceutical composition according to the present application can be formulated into types for oral or parenteral administration according to standard pharmaceutical practices. In addition to the active ingredient, these formulations can include additives such as pharmaceutically acceptable carriers, adjuvants, or diluents.

[0119] Suitable carriers include, for example, physiological saline, polyethylene glycol, ethanol, vegetable oil, and isopropyl myristate, and the like. Diluents include, for example, lactose, dextrose, sucrose, mannitol, sorbitol, cellulose, and / or glycine, and the like, but are not limited thereto. Further, the compound of the present application can be dissolved in oil, propylene glycol, or other solvents commonly used for the preparation of injection solutions. In addition, the compound of the present application can be formulated in the form of an ointment or cream for topical administration.

[0120] The preferred dose of the compound of the present application can vary depending on the condition and body weight of the patient, the severity of the disease, the type of drug, and the route and duration of administration, but can be appropriately selected by those skilled in the art. However, in order to achieve the desired effect, the compound of the present application can be administered at a dose of 0.0001 to 100 mg / kg (body weight), preferably 0.001 to 100 mg / kg (body weight) per day. It can be administered once a day or in divided doses per day by oral or parenteral route.

[0121] The pharmaceutical composition can contain 0.001% by weight to 99% by weight, preferably 0.01% by weight to 60% by weight of the compound of the present application, depending on the method of administration.

[0122] The pharmaceutical composition according to the present application can be administered to mammals such as rats, mice, livestock, humans by various routes. Administration can be performed by all possible methods, such as oral, rectal, intravenous, intramuscular, subcutaneous, intraendometrial, intracerebroventricular injection.

[0123] In this context, the symbol means a bond to another substituent.

[0124] In the present application, a halogen group means a fluoro group, a chloro group, a bromo group, or an iodo group.

[0125] In the present application, an alkyl group can be linear or branched. According to one embodiment, the number of carbons of the alkyl group is 1 to 10. According to another embodiment, the number of carbons of the alkyl group is 1 to 4. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, t-butyl, sec-butyl, 1-methylbutyl, 1-ethylbutyl, pentyl, n-pentyl, isopentyl, neopentyl, t-pentyl, 1-ethyl-propyl, 1,1-dimethylpropyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, iso-hexyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, octyl, n-octyl, t-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, and the like, but are not limited thereto. Furthermore, the explanation for the alkyl group can be applied to haloalkyl, except that at least one carbon of the alkyl group is substituted with a halogen group. Further, the explanation for the alkyl group can be applied to alkylene, except that the alkylene is a divalent group.

[0126] In the present application, the alkenyl group can be linear or branched. According to one embodiment, the number of carbons of the alkenyl group is 1 to 4. Specific examples of the alkenyl group include ethenyl, 1- propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, and the like, but are not limited thereto.

[0127] In the present application, the alkynyl group can be linear. According to one embodiment, the number of carbons of the alkynyl group is 1 to 4. Specific examples of the alkynyl group include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 3-butynyl, or 3-butynyl, and the like, but are not limited thereto.

[0128] In the present application, the alkoxy group refers to an alkyl group connected to oxygen through a single bond, and can be linear or branched. According to one embodiment, the number of carbons of the alkoxy group is 1 to 10. According to another embodiment, the number of carbons of the alkoxy group is 1 to 4. Specific examples of the alkoxy group include methoxy, ethoxy, propoxy, n-propoxy, isopropoxy, butoxy, n-butoxy, isobutoxy, t-butoxy, sec-butoxy, 1-methylbutoxy, 1-ethylbutoxy, pentoxy, n-pentoxy, isopentoxy, neopentoxy, t-pentoxy, 1-ethyl-propoxy, 1,1-dimethylpropoxy, hexoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 4-methyl-2-pentoxy, 3,3-dimethylbutoxy, 2-ethylbutoxy, heptoxy, n-heptoxy, isohexoxy, 1-methylhexoxy, 2-methylhexoxy, 3-methylhexoxy, 4-methylhexoxy, 5-methylhexoxy, octoxy, n-octoxy, t-octoxy, 1-methylheptoxy, 2-ethylhexoxy, 2,4,4-trimethyl-1-pentoxy, 2,4,4-trimethyl-2-pentoxy, 2-propylpentoxy, n-nonoxy, 2,2-dimethylheptoxy, n-decoxy, and the like, but are not limited thereto. Further, the explanation for the alkoxy group can be applied to the haloalkoxy group, except that at least one carbon of the alkoxy group is substituted with a halogen group.

[0129] In the present application, the cycloalkyl group is understood to mean a monovalent substituent derived from a saturated or unsaturated hydrocarbon ring compound, which contains only carbon as a ring-forming atom, but does not have aromaticity. According to one embodiment, the number of carbons of the cycloalkyl group is 3 to 10. According to another embodiment, the number of carbons of the cycloalkyl group is 3 to 8. According to still another embodiment, the number of carbons of the cycloalkyl group is 3 to 7. Specific examples of the cycloalkyl group include cyclopropyl, cyclobutyl, cyclopentyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, and the like, but are not limited thereto.

[0130] In the present application, an aryl group is understood to mean a monovalent substituent derived from a monocyclic or fused polycyclic compound which contains only carbon as a ring-forming atom and has aromaticity. According to one embodiment, the aryl group has a carbon number of 6 to 20. According to another embodiment, the aryl group has a carbon number of 6 to 12. According to still another embodiment, the aryl group has a carbon number of 6 to 10. Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, or a terphenyl group, but are not limited thereto. Further, examples of the fused polycyclic aryl group include a naphthyl group, an anthryl group, a phenanthryl group, a pyrenyl group, a perylenyl group, or a benzo[a]phenanthryl group, but are not limited thereto.

[0131] In the present application, a 6-membered N-containing heteroaryl group is understood to mean a monovalent substituent derived from a monocyclic compound which has aromaticity, contains N as a ring-forming atom in addition to carbon, and has 6 ring-forming atoms. Specific examples of the 6-membered N-containing heteroaryl group include a pyridyl group, a pyrimidinyl group, a pyridazinyl group, a pyrazinyl group, a triazinyl group, or a tetrazinyl group, but are not limited thereto.

[0132] In the present application, a 5- or 6-membered heterocyclic group is understood to mean a substituent derived from a monocyclic compound which has 5 or 6 ring-forming atoms, and contains 1 to 3 heteroatoms selected from O, N, and S in addition to carbon as a ring-forming atom. Further, the 5- or 6-membered heterocyclic group is understood to include all structures with or without aromaticity. Thus, the 5- or 6-membered heterocyclic group can be understood to include heterocycles having aromaticity and their hydrogenated derivatives. Further, the 5- or 6-membered heterocyclic group is substituted or unsubstituted by an oxo group (=O), wherein "substituted by an oxo group" means "containing carbon substituted by an oxo group (C=O)" other than carbon as a ring-forming atom. Specific examples of the 5- or 6-membered heterocyclic group containing 1 to 3 heteroatoms selected from N, O, and S, which is substituted or unsubstituted by an oxo group, include an imidazole ring, a pyrazole ring, a thiazole ring, an isothiazole ring, an oxazole ring, an isoxazole ring, a thiadiazole ring, an oxadiazole ring, a pyridine ring, a pyrimidine ring, a pyridazine ring, a pyrazine ring, a triazine ring, a tetrazine ring, a pyridine-2(1H)-one, and the like, but are not limited thereto.

[0133] Advantageous Effects The compound represented by Chemical Formula 1 according to the present application or a pharmaceutically acceptable salt thereof can be effectively used for the prevention or treatment of an inflammatory disease, an autoimmune disease, or cancer. DETAILED DESCRIPTION

[0134] Hereinafter, the present application will be described in more detail with reference to the following examples. However, these examples are for illustrative purposes only, and the scope of the present application is not limited thereto.

[0135] Preparation Example 1. 4,6-Dichloro-1-isopropyl-1 H -pyrrolo[3,2- cPreparation of 4,6-dichloro-1

[0136] 4,6-dichloro-1 H - pyrrolo [3, 2- c ] pyridine (5.61 g, 30 mmol) was dissolved in DMF (60 mL) and to this was added 2-iodopropane (3.59 mL, 36 mmol) and Cs2C03(24 g, 75 mmol). The reaction mixture was slowly heated and stirred at 60 °C for 1 h. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with distilled water. The organic layer was dried over MgS04, filtered and concentrated. The residue was purified by silica gel chromatography (0-50% dichloromethane / hexane) to synthesize 4,6-dichloro-1- isopropyl-1 H - pyrrolo [3, 2- c ] pyridine (5.1 g, 74% yield).

[0137] 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] + Preparation Example 2. 4,6-dichloro-1-methyl-1 H - pyrrolo [3, 2- c ] pyridine

[0138] The target compound (yield: 82%, white solid) was prepared in the same manner as in Preparation Example 1, except that iodomethane was used instead of 2-iodopropane used in Preparation Example 1.

[0139] 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] + Preparation Example 3. 4,6-dichloro-1-ethyl-1 H - pyrrolo [3, 2- c ] pyridine

[0140] The target compound (yield: 80%, white solid) was prepared in the same manner as in Preparation Example 1, except that ethyl iodide was used instead of 2-iodopropane used in Preparation Example 1.

[0141] LC-MS (ESI) m / z : 215[M+H] + Preparation Example 4. Preparation of 4,6-dichloro-1 H -pyrrolo[3,2- c ]pyridine

[0142] The target compound (yield: 81%, white solid) was prepared in the same manner as in Preparation Example 1, except that 1-iodopropane was used instead of 2-iodopropane used in Preparation Example 1.

[0143] LC-MS (ESI) m / z : 229[M+H] + Preparation Example 5. Preparation of 1-butyl-4,6-dichloro-1 H -pyrrolo[3,2- c ]pyridine

[0144] The target compound (yield: 77%, yellow oil) was prepared in the same manner as in Preparation Example 1, except that 1-iodopropane was used instead of 2-iodopropane used in Preparation Example 1.

[0145] LC-MS (ESI) m / z : 243[M+H] + Preparation Example 6. Preparation of 4,6-dichloro-1 H -pyrrolo[3,2- c ]pyridine

[0146] The target compound (yield: 84%, colorless oil) was prepared in the same manner as in Preparation Example 1, except that 1-bromo-2-methylpropane was used instead of 2-iodopropane used in Preparation Example 1.

[0147] LC-MS (ESI) m / z : 243[M+H] + Preparation Example 7. Preparation of ( S )-1-(sec-butyl)-4,6-dichloro-1 HPreparation of 4, 6-dichloro-1- (cyclopropylmethyl)-1H-pyrrolo[3, 2- c ]pyridine

[0148] The title compound (yield: 80%, colorless oil) was prepared in the same manner as in Preparation Example 1, except that (4-methylphenylsulfonyl)-sec-butyl ester was used instead of 2-iodopropane used in Preparation Example 1. R

[0149] LC-MS (ESI) m / z : 243[M+H] + Preparation Example 8. 4, 6-dichloro-1- (cyclopropylmethyl)-1H-pyrrolo[3, 2- R ]pyridine H Preparation of 4, 6-dichloro-1- (cyclopropylmethyl)-1H-pyrrolo[3, 2- c ]pyridine

[0150] The title compound (yield: 86%, colorless oil) was prepared in the same manner as in Preparation Example 1, except that (4-methylphenylsulfonyl)-sec-butyl ester was used instead of 2-iodopropane used in Preparation Example 1. S

[0151] LC-MS (ESI) m / z : 243[M+H] + Preparation Example 9. 4, 6-dichloro-1- (cyclopropylmethyl)-1H-pyrrolo[3, 2- H Preparation of 4, 6-dichloro-1- (cyclopropylmethyl)-1H-pyrrolo[3, 2- c ]pyridine

[0152] The title compound (yield: 90%, white solid) was prepared in the same manner as in Preparation Example 1, except that (bromomethyl)cyclopropane was used instead of 2-iodopropane used in Preparation Example 1.

[0153] LC-MS (ESI) m / z : 241[M+H] + Preparation Example 10. 4, 6-dichloro-1- (2-methylbutyl)-1H-pyrrolo[3, 2- H Preparation of 4, 6-dichloro-1- (2-methylbutyl)-1H-pyrrolo[3, 2- c ]pyridine

[0154] The title compound (yield: 80%, colorless oil) was prepared in the same manner as in Preparation Example 1, except that 1-bromo-2-methylbutane was used instead of 2-iodopropane used in Preparation Example 1. ​​

[0155] LC-MS (ESI) m / z : 257[M+H] + Preparation Example 11. Preparation of 4,6-dichloro-1-cyclopentyl-1 H -pyrrolo[3,2- c ]pyridine

[0156] The target compound (yield: 30%, white solid) was prepared in the same manner as in Preparation Example 1, except that bromocyclopentane was used instead of 2-iodopropane used in Preparation Example 1.

[0157] LC-MS (ESI) m / z : 255[M+H] + Preparation Example 12. Preparation of 4,6-dichloro-1-(cyclobutylmethyl)-1 H -pyrrolo[3,2- c ]pyridine

[0158] The target compound (yield: 30%, yellow solid) was prepared in the same manner as in Preparation Example 1, except that (bromomethyl)cyclobutane was used instead of 2-iodopropane used in Preparation Example 1.

[0159] LC-MS (ESI) m / z : 255[M+H] + Preparation Example 13. Preparation of 4,6-dichloro-1-(cyclopentylmethyl)-1 H -pyrrolo[3,2- c ]pyridine

[0160] The target compound (yield: 69%, white solid) was prepared in the same manner as in Preparation Example 1, except that (bromomethyl)cyclopentane was used instead of 2-iodopropane used in Preparation Example 1.

[0161] LC-MS (ESI) m / z : 269 [M+H] + Preparation Example 14. Preparation of 4,6-dichloro-1-((tetrahydrofuran-3-yl)methyl)-1 H -pyrrolo[3,2- c ]pyridine

[0162] The title compound (yield: 48%, yellow solid) was prepared in the same manner as in Preparation Example 1, except that 3-(bromomethyl)tetrahydrofuran was used instead of 2-iodopropane used in Preparation Example 1.

[0163] LC-MS (ESI) m / z : 271[M+H] + Preparation Example 15. Preparation of 4,6-dichloro-1-(3,3-dimethylbutyl)-1 H - pyrrolo [3,2- c ] pyridine

[0164] The title compound (yield: 88%, 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 used in Preparation Example 1.

[0165] LC-MS (ESI) m / z : 271[M+H] + Preparation Example 16. Preparation of 4,6-dichloro-1-(cyclohexylmethyl)-1 H - pyrrolo [3,2- c ] pyridine

[0166] The title compound (yield: 73%, white solid) was prepared in the same manner as in Preparation Example 1, except that (bromomethyl)cyclohexane was used instead of 2-iodopropane used in Preparation Example 1.

[0167] LC-MS (ESI) m / z : 283[M+H] + Preparation Example 17. Preparation of 4,6-dichloro-1-((tetrahydro-2 H - pyran-4-yl)methyl)-1 H - pyrrolo [3,2- c ] pyridine

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

[0169] LC-MS (ESI) m / z : 285[M+H] + Preparation Example 18. 4,6-Dichloro-l-(2-methoxyethyl)-l H Preparation of 5,6-dichloro-l-(2-methoxyethyl)-l c heteroaromatic compounds

[0170] The title compound (yield: 80%, 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 used in Preparation Example 1.

[0171] LC-MS (ESI) m / z : 245[M+H] + Preparation Example 19. 1-benzyl-4,6-dichloro-l H Preparation of 5,6-dichloro-l-(2-methoxyethyl)-l c heteroaromatic compounds

[0172] The title compound (yield: 67%, yellow syrup) was prepared in the same manner as in Preparation Example 1, except that (chloromethyl)benzene was used instead of 2-iodopropane used in Preparation Example 1.

[0173] LC-MS (ESI) m / z : 277[M+H] + Preparation Example 20. 4,6-dichloro-l-phenethyl-l H Preparation of 5,6-dichloro-l-(2-methoxyethyl)-l c heteroaromatic compounds

[0174] The title compound (yield: 77%, colorless syrup) was prepared in the same manner as in Preparation Example 1, except that (2-chloroethyl)benzene was used instead of 2-iodopropane used in Preparation Example 1.

[0175] LC-MS (ESI) m / z : 291[M+H] + Preparation Example 21. 4,6-dichloro-l-(difluoromethyl)-l H Preparation of 5,6-dichloro-l-(2-methoxyethyl)-l c heteroaromatic compounds

[0176] The title compound (yield: 30%, 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 used in Preparation Example 1.

[0177] LC-MS (ESI) m / z : 237[M+H] + Preparation Example 22. Preparation of 4,6-dichloro-1-(2,2,2-trifluoroethyl)-1 H - pyrrolo [3,2- c ] pyridine

[0178] The target compound (yield: 85%, white solid) was prepared in the same manner as in Preparation Example 1, except that 2,2,2-trifluoroethyl trifluoromethanesulfonate was used instead of 2-iodopropane used in Preparation Example 1.

[0179] LC-MS (ESI) m / z : 269[M+H] + Preparation Example 23. Preparation of 4,6-dichloro-1-(2,2-difluoroethyl)-1 H - pyrrolo [3,2- c ] pyridine

[0180] The target compound (yield: 93%, 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 used in Preparation Example 1.

[0181] LC-MS (ESI) m / z : 251[M+H] + Preparation Example 24. Preparation of 4,6-dichloro-1-(2,2-difluorocyclopropyl)-1 H - pyrrolo [3,2- c ] pyridine

[0182] The target compound (yield: 76%, 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 used in Preparation Example 1.

[0183] LC-MS (ESI) m / z : 263[M+H] + Preparation Example 25. ( R )-4,6-dichloro-1-(1,1,1-trifluoropropan-2-yl)-1 H - pyrrolo [3,2- c ] pyridine

[0184] The title compound (yield: 39%, white solid) was prepared in the same manner as in Preparation Example 1, except that 4,6-dichloro-1 S )-1,1,1-trifluoropropan-2-yl ester was used instead of 2-iodopropane used in Preparation Example 1.

[0185] LC-MS (ESI) m / z : 283[M+H] + Preparation Example 26. Preparation of 4,6-dichloro-1 H -1 c ]pyrrolo[3,2-

[0186] The title compound (yield: 48%, 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 used in Preparation Example 1.

[0187] LC-MS (ESI) m / z : 309[M+H] + Preparation Example 27. Preparation of 4,6-dichloro-1 H -1 c ]pyrrolo[3,2-

[0188] The title compound (yield: 59%, 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 used in Preparation Example 1.

[0189] LC-MS (ESI) m / z : 319[M+H] + Preparation Example 28. Preparation of 2-(4,6-dichloro-1 H -1 c ]pyrrolo[3,2-

[0190] Step 1. Preparation of 2-(4,6-dichloro-1 H -1 c ]pyrrolo[3,2- 4,6-dichloro-1 H -1 cPyridine (2.0 g, 10.7 mmol) was dissolved in DMF (20 mL) and to this was added 2-bromoacetonitrile (0.89 mL, 12.4 mmol) and Cs2CO3(5.23 g, 16.0 mmol). The reaction mixture was slowly heated and stirred at 60 °C for 1 h. The mixture was cooled to room temperature, diluted with ethyl acetate and washed with distilled water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0-50% ethyl acetate / hexane) to synthesize 2-(4,6-dichloro-l H - pyrrolo [3, 2- c ]pyridin- 1 -yl) acetonitrile as a light brown solid (1.78 g, yield: 74%).

[0191] 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] + Step 2. Preparation of 2-(4,6-dichloro-l H - pyrrolo [3, 2- c ]pyridin- 1 -yl)-2-methylpropanenitrile The 2-(4,6-dichloro-l H - pyrrolo [3, 2- c ]pyridin- 1 -yl) acetonitrile prepared in Step 1 (1.78 g, 7.9 mmol) was dissolved in DMF (20 mL) and to this was slowly added 60% NaH (0.79 g, 19.8 mmol) at 0 °C. The reaction mixture was stirred at 0 °C for 5 min and to this was slowly added Mel (1.5 mL, 24 mmol) and allowed to react at room temperature for 30 min. The reaction mixture was neutralized by the addition of 1 M aqueous HC1, diluted with ethyl acetate and washed with distilled water. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (20-30% ethyl acetate / hexane) to obtain the target compound as a light white solid (1.0 g, yield: 50%).

[0192] 1H NMR (500 MHz, CDCl3) δ 7.62 (s, 1H), 7.27 (d, J = 3.6 Hz, 1H), 6.70(d, J = 3.4 Hz, 1H), 2.09 (s, 7H). LC-MS (ESI) m / z: 226 [M+H] + Preparation Example 29. Preparation of 4,6-dichloro-l-isopentyl-l H - pyrrolo [3, 2- c ] pyridine

[0193] The target compound (yield: 73%, 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 used in Preparation Example 1.

[0194] LC-MS (ESI) m / z: 257 [M+H] + Preparation Example 30. Preparation of 4,6-dichloro-l-(pyridin-2-ylmethyl)-l H - pyrrolo [3, 2- c ] pyridine

[0195] The target compound (yield: 77%, yellow solid) was prepared in the same manner as in Preparation Example 1, except that 2-(chloromethyl)pyridine was used instead of 2-iodopropane used in Preparation Example 1.

[0196] LC-MS (ESI) m / z: 278 [M+H] + Preparation Example 31. Preparation of l-(4,6-dichloro-l H - pyrrolo [3, 2- c ] pyridin- 1 -yl)-2-methylpropan-2-ol

[0197] The target compound (yield: 80%, white solid) was prepared in the same manner as in Preparation Example 1, except that 2,2-dimethyloxirane was used instead of iodopropane used in Preparation Example 1.

[0198] LC-MS (ESI) m / z: 259 [M+H] + Preparation Example 32. Preparation of 4,6-dichloro-l-(2-fluoroethyl)-l HPreparation of 4, 6-dichloro-1- (2-iodopropyl) -1H- pyrrolo [3, 2- c ]pyridine

[0199] The title compound (yield: 72%, 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.

[0200] LC-MS (ESI) m / z: 233 [M+H] + Preparation Example 33. 4, 6-dichloro-1- (3-fluoropropyl) -1 H Preparation of 4, 6-dichloro-1- (2-iodopropyl) -1H- pyrrolo [3, 2- c ]pyridine

[0201] The title compound (yield: 78%, 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.

[0202] LC-MS (ESI) m / z: 247 [M+H] + Preparation Example 34. ( R )-4, 6-dichloro-1- (2-methylbutyl) -1 H Preparation of 4, 6-dichloro-1- (2-iodopropyl) -1H- pyrrolo [3, 2- c ]pyridine

[0203] The title compound (yield: 80%, colorless oil) was prepared in the same manner as in Preparation Example 1, except that (2R)-1-bromo-2-methylbutane was used instead of the 2-iodopropane used in Preparation Example 1.

[0204] LC-MS (ESI) m / z: 257 [M+H] + Preparation Example 35. ( S )-4, 6-dichloro-1- (2-methylbutyl) -1 H Preparation of 4, 6-dichloro-1- (2-iodopropyl) -1H- pyrrolo [3, 2- c ]pyridine

[0205] The title compound (yield: 80%, colorless oil) was prepared in the same manner as in Preparation Example 1, except that (2S)-1-bromo-2-methylbutane was used instead of the 2-iodopropane used in Preparation Example 1.

[0206] LC-MS (ESI) m / z: 257[M+H] + Example 1. Preparation of 1-(4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridin-1(2 H )-yl)prop-2-en-1-one

[0207] Step 1. Preparation of tert-butyl 4-(6-chloro-1-methyl-1 H - pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-1(2 H )-carboxylate Dissolve 4,6-dichloro-1 H - pyrrolo[3,2- c ]pyridine (201 mg, 1.0 mmol) in 1,4-dioxane (3.0 mL) then add to it tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2 H )-carboxylate (371 mg, 1.2 mmol), Pd(PPh3)4 (116 mg, 0.10 mmol), and 1 M aqueous Na2CO3 (2.0 mL) at room temperature. Slowly heat the reaction mixture and stir at 80 °C for 1 h. Cool the mixture to room temperature, then dilute with ethyl acetate and wash with distilled water. Dry the organic layer over MgSO4, filter, and concentrate. Purify the resulting residue by silica gel chromatography (0-40% ethyl acetate / hexanes) to synthesize tert-butyl 4-(6-chloro-1-methyl-1 H - pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-1(2 H )-carboxylate as a white solid (238 mg, yield: 68%).

[0208] 1H NMR (500 MHz, CDC13) 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 (brs, 2H), 2.80 (br s, 2H), 1.50 (s, 9H). LC-MS (ESI) m / z: 348 [M+H] + Step 2. Preparation of tert-butyl 4-(l-methyl-6-((5-methylthiazol-2-yl)amino)-lH- pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-l(2 H )-carboxylate Dissolve tert-butyl 4-(6-chloro-l-methyl-l H -hydropyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-l(2 H )-carboxylate (235 mg, 0.68 mmol) in 1,4-dioxane (4.0 mL), then add 5- methylthiazol-2-amine (117 mg, 1.0 mmol), Pd2(dba)3(62 mg), Xantphos (79 mg), and Cs2CO3(553 mg) thereto at room temperature. React the reaction mixture at 160 °C for 2 hours using a microwave reactor. Dilute the mixture with ethyl acetate, then wash with distilled water. Dry the organic layer with MgSO4, filter, and concentrate. Purify the resulting residue by silica gel chromatography (0-70% ethyl acetate / hexane) to synthesize tert-butyl 4-(l-methyl-6-((5-methylthiazol-2-yl)amino)-lH-pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-l(2 H )-carboxylate (30 mg, yield: 10%) as a yellow solid.

[0209] 1H NMR (500 MHz, CDC13) 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] + Step 3. Preparation of 1-(4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- d]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one c ] H tert-Butyl 4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- d]pyridin-4-yl)-3,6-dihydropyridine-1(2H)-carboxylate (30 mg, 0.070 mmol) was dissolved in CH2Cl2(3.0 mL), then TFA (2.0 mL) was added thereto, and stirred at room temperature for 1 hour. After completion of the reaction, the mixture was concentrated under reduced pressure to synthesize a salt compound. The resulting salt compound was dissolved in water (2.0 mL) and THF (4.0 mL), then NaHCO3(60 mg, 0.72 mmol) was added thereto, and stirred at room temperature for 10 minutes. The mixture was cooled to 0°C, then 1.0 M acryloyl chloride diluted in THF (0.091 mL, 1.3 eq) was slowly added dropwise thereto. 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 with MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0 to 10% methanol / dichloromethane) to synthesize 1-(4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- d]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one (14 mg, yield: 52%) as a white solid. c H c H

[0210] 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] + Examples 2 to 49 were prepared in a similar manner to Example 1, the structures and analytical results of these compounds are summarized in Table 1 below.

[0211] Table 1

[0212]

[0213]

[0214]

[0215]

[0216]

[0217]

[0218]

[0219] Example 50. N Preparation of tert-butyl (3-(6-chloro-l-methyl-lH-pyrrolo[3,2- c ]pyridin-4-yl)phenyl)carbamate

[0220] Step 1. Preparation of tert-butyl (3-(6-chloro-l-methyl-l H H-pyrrolo[3,2- c ]pyridin-4-yl)phenyl)carbamate tert-butyl (3-(6-chloro-l-methyl-lH-pyrrolo[3,2- H ]pyridin-4-yl)phenyl)carbamate (yield: 52%) was synthesized in the same manner as Step 1 of Example 1, except that (3-((tert-butoxycarbonyl)amino)phenyl)boronic acid was used instead of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-3,6-dihydropyridine-l(2 c )-carboxylic acid tert-butyl ester used in the synthetic Step 1 of Example 1. H LC-MS (ESI) m / z: 358 [M+H] +

[0221] Step 2. Preparation of tert-butyl (3-(l-methyl-6-((5-methylthiazol-2-yl)amino)-lH-pyrrolo[3,2- ]pyridin-4-yl)phenyl)carbamate c tert-butyl (3-(l-methyl-6-((5-methylthiazol-2-yl)amino)-lH-pyrrolo[3,2- ]pyridin-4-yl)phenyl)carbamate (yield: 27%) was synthesized in the same manner as Step 2 of Example 1, except that tert-butyl (3-(6-chloro-l-methyl-l c H-pyrrolo[3,2- H ]pyridin-4-yl)phenyl)carbamate was used instead of tert-butyl (3-(6-chloro-l-methyl-lH-pyrrolo[3,2- c]Pyridin-4-yl)phenyl)tert-butyl carbamate instead of 4-(6-chloro-1-methyl-1-yl)carbamate used in step 2 of the synthesis in Example 1 H -pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-1(2 H )-tert-butyl formate.

[0222] 1 H NMR (500 MHz, CDCl3) δ 8.53 (s, 1H), 8.12 (s, 1H), 7.82 (d, J = 6.9Hz, 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] + Step 3. N -(3-(1-methyl-6-((5-methylthiazo-2-yl)amino)-1H-pyrrolo[3,2-] c Preparation of pyridin-4-yl)phenyl)acrylamide N -(3-(1-methyl-6-((5-methylthiazo-2-yl)amino)-1H-pyrrolo[3,2-] c Pyridin-4-yl)phenyl)acrylamide (yield: 77%) was synthesized in the same manner as step 3 of Example 1, except that (3-(1-methyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-] ... c ]Pyridin-4-yl)phenyl)tert-butyl carbamate instead of 4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-1(2 H )-tert-butyl formate.

[0223] 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 = 3.1Hz, 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] + Examples 51 to 78 were prepared in a similar manner to Example 50, and the structures and analytical results of these compounds are summarized in Table 2 below.

[0224] Table 2

[0225]

[0226] Example 79. S )-1-(3-((1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2- cPreparation of tert-butyl (3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol

[0227] Step 1. Preparation of tert-butyl (3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol S -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol H -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol c Preparation of tert-butyl (3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol S -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol H -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol c -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol S -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol H -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol c -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol

[0228] 1 H NMR (500 MHz, CDCl3) δ 7.08 (m, 1H), 6.94 (m, 1H), 6.55 (d, J = 2.8Hz, 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] + Step 2. Preparation of tert-butyl (3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H- pyrrolo[3,2-b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol S -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol c -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol -3-((6-chloro-1-isopropyl-1H-pyrrolo[3,2- b]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol S)-3-((1-Isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c ]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol (yield: 69%) was synthesized in the same manner as Step 3 of Example 1, except that (R)-3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- S ]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol was used instead of 4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- H ]pyridin-4-yl)-3,6-dihydropyridine-1(2 c )-carboxylic acid tert-butyl ester used in the synthetic Step 3 of Example 1. H c LC-MS (ESI) m / z: 458 [M+H] + H Step 3. Preparation of (R)-1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- ]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol

[0229] LC-MS (ESI) m / z: 458 [M+H] + S Step 3. Preparation of (R)-1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c ]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol S (R)-1-(3-((1-Isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c ]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol (yield: 69%) was synthesized in the same manner as Step 3 of Example 1, except that (R)-3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- S ]pyridin-4-yl)oxy)piperidin-1-yl)propan-2-ol was used instead of 4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-1(2 c )-carboxylic acid tert-butyl ester used in the synthetic Step 3 of Example 1. H

[0230] 1 ​​H 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] + Examples 80 to 204 were prepared in a similar manner to Example 79, the structures and analytical results of these compounds are summarized in Table 3 below.

[0231] Table 3

[0232]

[0233] Example 205. ( S )-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1 H - pyrrolo[3,2- c ]pyridine-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one

[0234] Step 1. ( S )-3-((6-chloro-1-(2,2,2-trifluoroethyl)-1 H - pyrrolo[3,2- c ]pyridine-4-yl)oxy)pyrrolidine-1-carboxylic acid tert-butyl ester tert-Butyl 3-((6-chloro-1-(2,2,2-trifluoroethyl)-1 H - pyrrolo[3,2- c ]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate was prepared by dissolving 4,6-dichloro-1-(2,2,2-trifluoroethyl)-1 S - pyrrolo[3,2- S ]pyridine (269 mg, 1.0 mmol) in 1,4-dioxane (4.0 mL) then adding to it at room temperature tert-butyl 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). The reaction mixture was reacted at 130 °C for 1 h using a microwave reactor. The mixture was diluted with ethyl acetate then washed with distilled water. The organic layer was dried over MgSO4, filtered, and concentrated. The resulting residue was purified by silica gel chromatography (0-30% ethyl acetate / hexanes) to synthesize tert-butyl ( H )-3-((6-chloro-1-(2,2,2-trifluoroethyl)-1 c - pyrrolo[3,2- ]pyridine-4-yl)oxy)pyrrolidine-1-carboxylate as a white solid (268 mg, yield: 64%).

[0235] 1H NMR (500 MHz, CDC13) 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] + Step 2. Preparation of tert-butyl 3-((6-((5-methylthiazol-2-yl)amino)-1- (2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidine-1-carboxylate S H c S H c S H c H c H

[0236] 1 ​​​​​​​​​​​​​H 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 Hz, 1H), 4.52 (q, J = 8.4 Hz, 2H), 3.85-3.50 (m, 4H), 2.44-2.20 (m, 5H), 1.48 (d, J =11.4 Hz, 8H). LC-MS (ESI) m / z: 498 [M+H] + Step 3. S )-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1 H -pyrrolo[3,2- c Preparation of pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one ( S )-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1 H -pyrrolo[3,2- c ]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one (yield: 64%) was synthesized in the same manner as step 3 of Example 1, except that ( S )-3-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1 H -pyrrolo[3,2- c ]Pyridin-4-yl)oxy)pyrrolidine-1-carboxylic acid tert-butyl ester instead of 4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-] c ]pyridin-4-yl)-3,6-dihydropyridine-1(2 H )-tert-butyl formate.

[0237] 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 = 42.8Hz, 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] + Examples 206 to 223 were prepared in a similar manner to Example 205, the structures and analytical results of these compounds are summarized in Table 4 below.

[0238] Table 4

[0239] Example 224. ( S )-2-Fluoro-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2- c ]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one

[0240] Step 1. ( S )-3-((6-Chloro-1-isopropyl-1 H -pyrrolo[3,2- cPreparation of tert-butyl pyridine-4-yl)oxy)pyrrolidine-1-carboxylate Will( S 1.76 g (9.4 mmol) of tert-butyl 1-hydroxypyrrolidine-1-carboxylate was dissolved in 10.0 mL of THF, and then 60% NaH (469 mg, 11.2 mmol) was slowly added to it at 0 °C. The reaction mixture was stirred at 0 °C for 30 minutes, and then 4,6-dichloro-1-isopropyl-1-carboxylate was added. H -pyrrolo[3,2- c Pyridine (1.90 g, 7.8 mmol) was added, and the reaction was allowed to proceed at 60 °C for 6 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, and washed with an aqueous solution of ammonium chloride. The organic layer was dried over MgSO4, filtered, and concentrated. The residue was purified by silica gel chromatography (0–30% ethyl acetate / hexane) to obtain the synthesis of a white solid ( S )-3-((6-chloro-1-isopropyl-1 H -pyrrolo[3,2- c 1-Ter-butyl pyridin-4-yl)oxy)pyrrolidine-1-carboxylate (2.00 g, yield: 65%).

[0241] 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 = 6.6Hz, 6H).; LC-MS (ESI) m / z : 394 [M+H] + Step 2. S )-3-((1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2- c Preparation of tert-butyl pyridine-4-yl)oxy)pyrrolidine-1-carboxylate ( S )-3-((1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2- c ]Pyridin-4-yl)oxy)pyrrolidine-1-carboxylic acid tert-butyl ester (yield: 42%) was synthesized in the same manner as step 2 of Example 1, except that (S )-3-((6-chloro-1-isobutyl-1 H -pyrrolo[3,2- c ]Pyridin-4-yl)oxy)pyrrolidine-1-carboxylic acid tert-butyl ester instead of 4-(6-chloro-1-methyl-1-yl)pyrrolidine-1-carboxylic acid tert-butyl ester used in step 2 of the synthesis in Example 1 H -pyrrolo[3,2- c ]pyridin-4-yl)-3,6-dihydropyridine-1(2 H )-tert-butyl formate.

[0242] LC-MS (ESI) m / z: 472 [M+H] + Step 3. S )-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2- c Preparation of pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one Will( S )-3-((1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2- c 118 mg (0.25 mmol) of tert-butyl pyridin-4-yl)oxy)pyrrolidine-1-carboxylate was dissolved in CH2Cl2 (2.0 mL), and then TFA (1.5 mL) was added. 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 resulting salt compound was dissolved in THF (2.0 mL), and 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. 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 residue was purified by silica gel chromatography (70% ethyl acetate / hexane) to synthesize a white solid ( S )-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2- c Pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one (45 mg, yield: 41%).

[0243] 1H 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] + Examples 225 to 231 were prepared in a similar manner to Example 224, the structures and analytical results of these compounds are summarized in Table 5 below.

[0244] Table 5

[0245] Experimental Examples: Inhibitory activity against BTK and ITK The inhibitory activity against BTK and ITK of the compounds prepared in the above examples was measured as follows.

[0246] The inhibitory activity against BTK and ITK was evaluated using the "ADP-Glo™ Kinase System" (Promega Corporation). In the case of this evaluation method, the activation was measured by quantifying the amount of ADP produced during the kinase reaction, which is used to measure the inhibitory activity against BTK and ITK.

[0247] Specifically, the inhibitory activity against BTK and ITK was measured using BTK kinase (Signalchem, B10-10H), ITK kinase (Signalchem, I13-11G-10), and ADP-Glo kinase assay kit (Promega, V9102). Purified recombinant human BTK and ITK were diluted with 1 x kinase reaction buffer (40 mM Tris-Cl, pH 7.5, 20 mM MgCl2, 0.1 mg / mL BSA, 2 mM MnCl2, and 50 uM DTT) and added to a 96-well plate (ITK: final concentration of 4 ng per reaction / BTK: final concentration of 10 ng per reaction). The compounds prepared in the foregoing examples were treated so as to be finally 1% DMSO aqueous solution, and a substrate mixture containing ATP (1 mM or Km ATP (BTK: 10 uM / ITK: 25 uM)) and 0.2 ug / ul of poly(Glu4, Tyr1) peptide (BTK and ITK final concentration) in a total of 25 uL of the reaction was added to the 96-well plate to initiate the enzymatic reaction. After incubation (30°C) for 1 hour, an equal volume (25 uL per reaction) of ADP Glo was added and incubated at room temperature (30°C) for 40 minutes. Then, the kinase detection reagent (45 uL per reaction) was added and incubated at room temperature (30°C) for 30 minutes. The kinase activity was measured by chemiluminescence according to the instructions of the ADPGlo kinase assay kit, and the inhibitory activity of the compound according to the present application was calculated. For the analysis of the results of each compound, Microsoft Excel was used, and IC 50 values were calculated by GraphPad Prism software.

[0248] According to the range of the obtained IC 50 values, the inhibitory activity of each compound was classified as A, B, C, and D as follows, and these are shown in Table 6 below.

[0249] A: when the obtained IC 50 value is 20 nM or less B: when the obtained IC 50 value is greater than 20 nM and is 100 nM or less C: when the obtained IC 50 value is greater than 100 nM and is 500 nM or less D: when the obtained IC 50 value is greater than 500 nM Table 6 。

Claims

1. A compound represented by the following chemical formula 1, or a pharmaceutically acceptable salt thereof, [Chemical Formula 1] In chemical formula 1, Y1 is a single bond, C 1-4 Alkylene or C 1-4 Halogenated alkylene, R1 is C 1-10 Alkyl, C 1-10 Alkoxy, C 3-10 cycloalkyl, C 6-20 Aryl, nitrogen-containing 6-membered heteroaryl, tetrahydrofuranyl, or tetrahydropyranyl, Where R1 is unsubstituted or substituted by one or more substituents selected from the group consisting of: halogen, cyano, hydroxyl, C 1-4 Alkyl and C 1-4 Halogenated alkyl groups, A is a benzene ring; or a 5- or 6-membered heterocycle containing 1 to 3 heteroatoms selected from the group consisting of N, O, and S, substituted with an oxo group (=O) or unsubstituted, provided that the 5- or 6-membered heterocycle contains at least one N atom. R2 can be independently hydrogen, halogen, cyano, or C. 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy, C 1-4 Halogenated alkoxy or -CONH(C 1-4 alkyl), k is 1 or 2, Y2 is a single bond, -O-, or -O- (C 1-4 Alkylene), L is any of the linker groups represented by the following chemical formulas 2a to 2k. In chemical formulas 2a to 2k n is 0, 1, 2, or 3. Z is independently a halogen, C 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy or C 1-4 Halogenated alkoxy groups, Each 'a' can be independently 0, 1, or 2. L' represents methylene, ethylene, or methylene-O-methylene. v and w are each independently 0, 1, or 2. The condition is that v+w is an integer from 0 to 3. p to s are each independently 0, 1, 2, 3 or 4. The condition is that p+q and r+s are each an independent integer from 2 to 4. * indicates the point connected to Y2 in chemical formula 1. X is either CO or SO2, and R3 is C 1-4 Alkyl, C 2-4 alkenyl or C 2-4 alkynyl group, Where R3 is unsubstituted or substituted by one or more substituents selected from the group consisting of: halogens, NH2, NH(C) 1-4 alkyl) and N(C) 1-4 Alkyl)2.

2. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein: Y1 is a single bond, methylene, or ethylene.

3. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein: 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, pyridyl, tetrahydrofuranyl, or tetrahydropyranyl. R1 is either unsubstituted or substituted by one to three substituents selected from the group consisting of: chlorine, fluorine, cyano, hydroxyl, methyl, monofluoromethyl, difluoromethyl and trifluoromethyl.

4. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: A can be a benzene ring, thiazole ring, thiadiazole ring, imidazole ring, pyrazole ring, pyrazine ring, pyridine ring, pyrimidine ring, or pyridine-2(1H)-ketone ring.

5. The compound according to claim 1 or a pharmaceutically acceptable salt thereof, wherein: R2 can be hydrogen, chlorine, fluorine, cyano, methyl, ethyl, monofluoromethyl, difluoromethyl, trifluoromethyl, methoxy, or -CONH (methyl).

6. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: Y2 is a single bond, -O-, or -O- (methylene).

7. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: When Y2 is a single bond, L is any of the linkers represented by chemical formulas 2a to 2g.

8. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: When Y2 is -O- or -O-(C 1-4 When L is an alkylene group, L is any of the linking groups represented by chemical formulas 2h to 2k.

9. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: L is any linker selected from the groups represented by the following: in, Z and a are as defined in claim 1, and * refers to the point connected to Y2 in chemical formula 1.

10. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: Z can be chlorine, fluorine, methyl, or methoxy.

11. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: R3 can be -CH3, -CH=CH2, -CH=CHCH3, -C≡CH, or -C≡CCH3. R3 is either unsubstituted or substituted by one or two substituents selected from the group consisting of: chlorine, fluorine, NH2, NH(methyl) and N(methyl)2.

12. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: The compound represented by chemical formula 1 is represented by any of the following chemical formulas 1-1 to 1-3: [Chemical Formula 1-1] [Chemical Formula 1-2] [Chemical Formulas 1-3] In chemical formulas 1-1 to 1-3, R'2 is a halogen, cyano group, or C group. 1-4 Alkyl, C 1-4 Haloalkyl, C 1-4 Alkoxy, C 1-4 Halogenated alkoxy or -CONH(C 1-4 alkyl), Y1, R1, R2, Y2, L and R3 are as defined in claim 1.

13. The compound of claim 1 or a pharmaceutically acceptable salt thereof, wherein: The compound represented by chemical formula 1 is selected from any of the following groups: 1) 1-(4-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 2) 1-(4-(1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 3) 1-(3-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2,5-dihydro-1H-pyrrolo-1-yl)prop-2-en-1-one, 4) 1-(4-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 5) 1-(4-(1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 6) 1-(4-(1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 7) 1-(4-(1-(cyclobutylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 8) 1-(4-(6-((5-methylthiazol-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 9) 1-(4-(1-(cyclohexylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 10) 1-(4-(1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 11) 1-(4-(1-((4,4-difluorocyclohexyl)methyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 12) 1-(4-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 13)(S)-1-(4-(1-(sec-butyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 14)(R)-1-(4-(1-(sec-butyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 15) 1-(4-(1-benzyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 16) 1-(4-(6-((5-methylthiazol-2-yl)amino)-1-phenethyl-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 17) 1-(4-(6-((5-methylthiazol-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 18) 1-(4-(1-(3,3-dimethylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 19) 1-(4-(6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 20) 1-(4-(1-(2,2-difluorocyclopropyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 21) 1-(4-(1-(difluoromethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 22) 2-(4-(1-Acryloyl-1,2,3,6-tetrahydropyridin-4-yl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropionitrile, 23) 2-(4-(1-Acryloyl-1,2,5,6-tetrahydropyridin-3-yl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-1-yl)-2-methylpropionitrile, 24)(R)-1-(4-(6-((5-methylthiazol-2-yl)amino)-1-(1,1,1-trifluoroprop-2-yl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 25) 1-(4-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3-methyl-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 26) 1-(4-(1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2,3,6,7-tetrahydro-1H-azaphen-1-yl)propyl-2-en-1-one, 27) 1-(7-(1-isopropyl-6-((5-methylthiazolyl-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-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 29) 1-(3-(1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 30) 1-(3-(6-((5-methylthiazol-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 31) 1-(3-(1-(2,2-difluorocyclopropyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 32) 1-(3-(1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 33) 1-(3-(1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 34) 1-(3-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 35) 1-(3-(6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 36) 1-(3-(1-methyl-6-((5-methylthiazol-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-methylthiazolyl-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-methylthiazolyl-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-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-8-azabicyclo[3.2.1]oct-2-en-8-yl)prop-2-en-1-one, 40) 1-(4-(6-((1H-imidazol-2-yl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)prop-2-en-1-one, 41) 1-(4-(1-isopropyl-6-((5-methyl-1,3,4-thiadiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 42) 1-(4-(1-isopropyl-6-((4-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 43) 1-(4-(1-isopropyl-6-(pyrimidin-4-ylamino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 44) 1-(4-(1-isopropyl-6-((6-methylpyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 45) 1-(4-(1-isopropyl-6-((6-(trifluoromethyl)pyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 46) 1-(4-(1-isopropyl-6-((6-methoxypyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 47) 1-(4-(6-((4-fluoropyridin-2-yl)amino)-1-isopropyl-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 48) 1-(4-(1-isopropyl-6-((4-(trifluoromethyl)pyridin-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 49) 1-(4-(1-isopropyl-6-((4-methylpyridin-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-3,6-dihydropyridin-1(2H)-yl)propyl-2-en-1-one, 50)N-(3-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 51)N-(2-fluoro-3-(1-methyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 52)N-(2-methoxy-3-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 53)N-(3-methyl-5-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 54)N-(2-fluoro-5-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 55)N-(2-methyl-5-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 56) N-(2,6-dimethyl-3-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 57)N-(2,6-difluoro-3-(1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 58)N-(3-(1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2-methylphenyl)acrylamide, 59)N-(4-fluoro-3-(1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 60)N-(2,4-difluoro-5-(1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 61)N-(3-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-4-fluorophenyl)acrylamide, 62)N-(3-(1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2-methylphenyl)acrylamide, 63)N-(4-fluoro-3-(1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 64)N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2-fluorophenyl)acrylamide, 65)N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2-methylphenyl)acrylamide, 66)N-(5-(1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2,4-difluorophenyl)acrylamide, 67)N-(2,4-difluoro-5-(1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 68)(S)-N-(3-(1-(sec-butyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-4-fluorophenyl)acrylamide, 69)N-(5-(1-(3,3-dimethylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2,4-difluorophenyl)acrylamide, 70)N-(3-(1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-4-fluorophenyl)acrylamide, 71)N-(4-fluoro-3-(6-((5-methylthiazolyl-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 72)N-(2-fluoro-5-(6-((5-methylthiazolyl-2-yl)amino)-1-((tetrahydrofuran-3-yl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 73)N-(2-fluoro-3-(6-((5-methylthiazolyl-2-yl)amino)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 74)N-(5-(1-(2,2-difluoroethyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2-methylphenyl)acrylamide, 75)N-(3-(1-(2,2-difluoroethyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-4-fluorophenyl)acrylamide, 76)N-(5-(1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)-2-fluorophenyl)acrylamide, 77)N-(2,4-difluoro-5-(6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 78)N-(4-fluoro-3-(6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)phenyl)acrylamide, 79)(S)-1-(3-((1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 80)1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)azacyclobutane-1-yl)prop-2-en-1-one, 81)(S)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 82)(R)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 83) 1-((3S,4R)-3-fluoro-4-((1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 84)(S)-1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 85)(S)-1-(2-(((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 86)(S)-1-(2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)azacyclobutane-1-yl)prop-2-en-1-one, 87)1-((2R,4S)-4-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 88)1-((2S,4S)-4-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 89)(R)-1-(2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 90)(R)-1-(2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)azacyclobutane-1-yl)prop-2-en-1-one, 91)1-((3R,4R)-3-fluoro-4-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 92) Racemic-1-((3S,4R)-3-((1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-methylpyrrolidine-1-yl)prop-2-en-1-one, 93)(R)-1-(4,4-difluoro-2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 94)1-((2R,4S)-2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)-4-methoxypyrrolidine-1-yl)prop-2-en-1-one, 95)(S)-1-(3-((1-isopropyl-6-((6-(trifluoromethyl)pyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 96)1-((2R,4S)-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 97)(S)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 98)1-((2R,4S)-4-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 99)(S)-1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 100)1-((2R,4S)-4-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 101)(S)-1-(3-((1-isopropyl-6-((6-methylpyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 102)(S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 103)(S)-1-(3-((1-isopropyl-6-((6-methoxypyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 104)(S)-1-(3-((1-isobutyl-6-((6-methylpyrimidin-4-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 105)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 106)1-((3R,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 107)1-((3R,4S)-3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 108)1-((3R,4R)-3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 109)1-((3R,4S)-3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 110)1-((3R,4R)-3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 111)1-((S)-3-((1-((S)-sec-butyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 112)1-((3R,4S)-3-((1-((S)-sec-butyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 113)1-((3R,4R)-3-((1-((S)-sec-butyl)-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 114)(S)-1-(3-((1-isopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 115)1-((3R,4R)-3-fluoro-4-((1-isopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 116)1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-methylpyrrolidine-1-yl)prop-2-en-1-one, 117)(S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-(pyridin-2-ylmethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 118)1-(3-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)azacyclobutane-1-yl)prop-2-en-1-one, 119)1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-3-methylazacyclobutane-1-yl)prop-2-en-1-one, 120)1-((3R,4R)-3-fluoro-4-((6-((5-methylthiazol-2-yl)amino)-1-((1-(trifluoromethyl)cyclopropyl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 121)(S)-1-(3-((1-benzyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 122)(S)-1-(3-((6-((5-ethylthiazol-2-yl)amino)-1-isobutyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 123)1-((3S)-3-((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 124)(S)-1-(3-((1-butyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 125)(S)-1-(3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 126)(S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 127)(S)-1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 128)(S)-1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 129)(S)-1-(3-((1-(cyclohexylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 130)(S)-1-(3-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 131)1-((3S,4R)-3-fluoro-4-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 132)1-((3R,4S)-3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 133)(S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-((tetrahydro-2H-pyran-4-yl)methyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 134)1-((3S,4S)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 135)1-((3R,4S)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 136)1-(6-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-1-azaspiro[3.3]heptane-1-yl)prop-2-en-1-one, 137)1-(6-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-1-azaspiro[3.3]heptane-1-yl)prop-2-en-1-one, 138)(S)-1-(3-((6-((5-fluoro-2-methylphenyl)amino)-1-methyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-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]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 140)(S)-1-(3-((1-(2-hydroxy-2-methylpropyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 141) 1-((3S,4R)-3-fluoro-4-((1-(2-hydroxy-2-methylpropyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 142)1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)azacyclobutane-1-yl)prop-2-en-1-one, 143)(R)-1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 144)(R)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 145)1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)azacyclobutane-1-yl)prop-2-en-1-one, 146) 1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)azacyclobutane-1-yl)prop-2-en-1-one, 147) 1-((3S,4R)-3-fluoro-4-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 148)(S)-1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 149)(S)-1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 150)(S)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 151)(S)-1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 152)1-((3R,4S)-3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 153)(S)-1-(3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 154)1-((3R,4R)-3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidin-1-yl)prop-2-en-1-one, 155)1-(3-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-3-methylazacyclobutane-1-yl)prop-2-en-1-one, 156)(R)-1-(3-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 157)1-((3R,4R)-3-fluoro-4-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 158)(S)-1-(3-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 159)1-((3S,4R)-3-fluoro-4-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 160)(S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 161)1-((3R,4R)-3-fluoro-4-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 162)(R)-1-(3-((1-isopropyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 163)1-(3-((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-3-methylazacyclobutane-1-yl)prop-2-en-1-one, 164)1-((2S,4S)-4-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 165)1-(3-((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-3-methylazacyclobutane-1-yl)prop-2-en-1-one, 166) 1-(3-methyl-3-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)azacyclobutan-1-yl)prop-2-en-1-one, 167) 1-(3-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-3-methylazacyclobutane-1-yl)prop-2-en-1-one, 168)1-(3-((1-(2-methoxyethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-3-methylazacyclobutane-1-yl)prop-2-en-1-one, 169)(S)-1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 170)1-((3R,4R)-3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-4-fluoropyrrolidine-1-yl)prop-2-en-1-one, 171)1-((3S,4R)-3-fluoro-4-((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 172)1-((3S)-3-((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)piperidin-1-yl)prop-2-en-1-one, 173)1-((3R,4R)-3-fluoro-4-((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 174)1-((3R,4R)-3-fluoro-4-((1-((R)-2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 175)1-((3R,4R)-3-fluoro-4-((1-((S)-2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 176) 1-(3-methyl-3-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)azacyclobutane-1-yl)prop-2-en-1-one, 177)1-(3-((1-isopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-3-methylazacyclobutane-1-yl)prop-2-en-1-one, 178) 1-(3-((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-3-methylazacyclobutane-1-yl)prop-2-en-1-one, 179)1-((2S,4S)-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 180)1-((2S,4S)-4-((1-(cyclopropylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-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]pyridin-6-yl)amino)thiazole-5-carboxynitrile, 182)2-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridin-6-yl)amino)-N-methylthiazolyl-5-carboxamide, 183)(S)-1-(3-((1-isopropyl-6-((4-methoxypyrimidin-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 184)(S)-1-(3-((1-isopropyl-6-((3-methoxypyrazin-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 185)1-((2S,4S)-2-methyl-4-((1-methyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 186)1-((2S,4S)-4-((1-ethyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-methylpyrrolidine-1-yl)prop-2-en-1-one, 187)1-((2S,4S)-2-methyl-4-((6-((5-methylthiazol-2-yl)amino)-1-propyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 188)(S)-1-(3-((1-(2-fluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 189)1-((3S,4R)-3-fluoro-4-((1-(2-fluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 190)(S)-1-(3-((1-(3-fluoropropyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 191)1-((3S,4R)-3-fluoro-4-((1-(3-fluoropropyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 192)(S)-1-(3-((6-((1H-pyrazol-3-yl)amino)-1-isopropyl-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 193)(S)-1-(3-((1-isopropyl-6-((1-methyl-1H-pyrazol-3-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 194)(S)-1-(3-((1-isopropyl-6-((5-methyl-1H-pyrazol-3-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 195)1-((3R,4S)-3-((6-(((1H-pyrazol-3-yl)amino)-1-isobutyl-1H-pyrrolo[3,2-c]pyridin-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-pyrazol-3-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 197)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((1-methyl-1H-pyrazol-3-yl)amino)-1H-pyrrolo[3,2-c]pyridin-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]pyridin-6-yl)amino)-1-methylpyridin-2(1H)-one, 199)3-((4-(((3R,4S)-1-acryloyl-4-fluoropyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridin-6-yl)amino)-1-methylpyridin-2(1H)-one, 200)1-(2-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-5-azaspiro[3,4]octane-5-yl)prop-2-en-1-one, 201)1-(7-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-1-azaspiro[4,4]nonane-1-yl)prop-2-en-1-one, 202)1-(2-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-6-azaspiro[3,4]octane-6-yl)prop-2-en-1-one, 203)1-(2-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-5-azaspiro[3,5]nonane-5-yl)prop-2-en-1-one, 204)1-(7-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)-2-azaspiro[4,4]nonane-2-yl)prop-2-en-1-one, 205)(S)-1-(3-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 206)(S)-1-(3-((1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 207)(R)-1-(2-(((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 208)(R)-1-(2-(((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)azacyclobutane-1-yl)prop-2-en-1-one, 209)(R)-1-(2-(((1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)azacyclobutane-1-yl)prop-2-en-1-one, 210)(R)-1-(2-(((1-(2,2-difluoroethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 211)1-((3S,4R)-3-fluoro-4-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 212)1-((2R,4S)-2-methyl-4-((6-((5-methylthiazol-2-yl)amino)-1-(2,2,2-trifluoroethyl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 213)1-((S)-3-((6-((5-methylthiazol-2-yl)amino)-1-((R)-1,1,1-trifluoroprop-2-yl)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidine-1-yl)prop-2-en-1-one, 214)(R)-1-(3-(((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)piperidin-1-yl)prop-2-en-1-one, 215)(S)-1-(3-(((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)piperidin-1-yl)prop-2-en-1-one, 216)(S)-1-(3-(((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 217)1-(2-(((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 218)1-(2-(((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)azacyclobutane-1-yl)prop-2-en-1-one, 219)(S)-1-(2-(((1-isopropyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 220)(S)-1-(2-(((1-(cyclopentylmethyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 221)1-((2S)-2-(((1-(2-methylbutyl)-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidine-1-yl)prop-2-en-1-one, 222)(S)-1-(2-(((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)pyrrolidin-1-yl)prop-2-en-1-one, 223)(R)-1-(2-(((1-cyclopentyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)methyl)azacyclobutane-1-yl)prop-2-en-1-one, 224)(S)-2-fluoro-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-en-1-one, 225)(S)-1-(3-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-yn-1-one, 226)(S,E)-1-(3-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)but-2-en-1-one, 227)(S,E)-4-(dimethylamino)-1-(3-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)but-2-en-1-one, 228)N-(4-(((3R,4S)-4-fluoro-1-(vinylsulfonyl)pyrrolidine-3-yl)oxy)-1-isobutyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-5-methylthiazolyl-2-amine, 229)2-Chloro-1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)acet-1-one, 230)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazol-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)but-2-yn-1-one, and 231)1-((3S,4R)-3-fluoro-4-((1-isobutyl-6-((5-methylthiazolyl-2-yl)amino)-1H-pyrrolo[3,2-c]pyridin-4-yl)oxy)pyrrolidin-1-yl)prop-2-yn-1-one.

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

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

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