Autophagy-activating compounds

Abstract

The present application discloses, as one embodiment of the invention, a compound represented by formula (I) (in the formula, each symbol is as defined in the description) or a pharmaceutically acceptable salt thereof. The compound activates autophagy functions, and is useful as a prophylactic or a therapeutic agent for diseases caused by a decline in autophagy functions or diseases in which a pathological condition is suppressed or improved by the enhancement of an autophagy function.

Description

[Technical Field]

[0001] The present invention provides, as one embodiment thereof, a compound that has the effect of activating autophagy function and is useful as a pharmaceutical, and is useful, for example, in the field of medicine. [Background technology]

[0002] Autophagy is an intracellular degradation mechanism in which a portion of the cytoplasm is surrounded by an isolation membrane to form a membrane structure called an autophagosome, which then fuses with a lysosome to form an autolysosome, thereby breaking down waste products, unnecessary proteins, and other substances. Autophagy plays an important role in physiological and pathological functions in living organisms, and numerous diseases and symptoms have been reported in recent years, including those caused in part by a decrease in autophagy, and those whose pathology is suppressed or improved by the enhancement of autophagy. Examples of such diseases and symptoms include neurodegenerative diseases, infectious diseases, inflammatory diseases, immune diseases, kidney diseases, respiratory diseases, eye diseases, muscle diseases, mitochondrial diseases, lifestyle-related diseases, skin aging, and various other diseases or symptoms (Patent Document 1). Therefore, various pharmaceuticals and foods containing active ingredients that activate autophagy have been investigated for the prevention or treatment of diseases and symptoms caused in part by decreased autophagy, or diseases and symptoms whose pathology can be suppressed or improved by enhancing autophagy (Patent Documents 1 to 3). However, in the medical field, there is a demand for drugs that activate a wider variety of autophagy functions. For this reason, the creation of compounds that activate autophagy with structures that are different from conventional ones has been awaited.

[0003] Although compounds having an azaindole skeleton have been known (for example, Patent Document 4), there have been no reports of compounds that can activate autophagy function. [Prior art documents] [Patent documents]

[0004] [Patent Document 1] Japanese Patent Publication No. 2023-174643 [Patent Document 2] International Publication No. 2022 / 054926 [Patent Document 3] International Publication No. 2022 / 054927 [Patent Document 4] International Publication No. 2011 / 019060 Summary of the Invention [Problem to be solved by the invention]

[0005] An object of the present invention is to provide, as one embodiment, a compound that has the effect of activating autophagy function and is useful as a preventive or therapeutic agent for diseases caused by decreased autophagy function or diseases whose pathology can be suppressed or ameliorated by enhancing autophagy function. [Means for solving the problem]

[0006] The present inventors have conducted extensive research to solve the above problems and have completed the present invention. Specific embodiments of the present invention are as follows. However, the present invention is not limited to these.

[0007] [1] Formula (I):

[0008] [ka]

[0009] [In the formula, R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form the following formulae (IIa) to (IIe):

[0010] [ka]

[0011] (In the formula, Rx and Ry each independently represent an oxo group, an optionally substituted aryloxy group, or an optionally substituted C 1-6 represents an alkyl group, wherein two Rx and two Ry may each independently be joined together with the carbon atom to which they are attached to form a heterocycloalkane or a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 represents an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R 1 and R 2 each independently represents an optionally substituted C 1-6 represents an alkyl group; fR 3 are each independently 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R 3a is a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; A represents an optionally substituted divalent hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; g indicates 0 or 1; Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, optionally substituted aromatic heterocyclic group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or -COR e (R e may be substituted C 1-6 (Alkyl group) may be substituted with; M 1 may be substituted C 1-4 represents an alkylene group; M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO-, -(CH2) j4 -CO-(CH2) j5 -, -(CH2) j6 -CH(R)-(CH2) j7-, -(CH2) j8 -S-(CH2) j9 -, or -NR a6 -(In the formula, R a4 ~R a6 is as described below, and j1 to j9 each independently represent an integer of 0 to 4; R represents a hydroxyl group or an aryl group; R a1 ~R a6 , and R b1 ~R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8 an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or -COR f (R f is C 1-6 alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group; R c1 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group), or an optionally substituted aryl group. however, (1) M 1 is -(CH2)-, g is 0, and M 2 Ga-(CH2) j1 - when j1 is 0 and Q is benzene R 4 is not a pyrazolyl group substituted with a methyl group. (2) M 1 is -(CH2)-, g is 1, A is benzene, and M 2 But -(CH2) j1 - when j1 is 0 and Q is pyrazole R 4 is not a methyl group. or a pharmaceutically acceptable salt thereof. [2]R 1 and R 2 together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe):

[0012] [ka]

[0013] wherein Rx and Ry each independently represent an oxo group, an optionally substituted C 6-14 an aryloxy group or an optionally substituted C 1-6 alkyl group, wherein two Rx and two Ry are each independently joined together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R 1 and R 2 each independently represents an optionally substituted C 1-6 is an alkyl group; fR 3 are each independently 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), C 6-14 Aryl group, 5- to 8-membered aromatic heterocyclic group, -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R 3a is a hydrogen atom or C1-6 represents an alkyl group; A is an optionally substituted divalent C 3-14 a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or an optionally substituted 3- to 8-membered heterocycloalkylene group; Q is C 1-6 Alkyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, optionally substituted 5- to 8-membered aromatic heterocyclic group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group), or -COR e (R e may be substituted C 1-6 (Alkyl group) may be substituted with; R a1 ~R a3 , and R b1 ~R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8 Alkynyl group, optionally substituted C 3-14a hydrocarbon ring group, an optionally substituted 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 alkyl group, optionally substituted C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group); R c1 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group), or optionally substituted C 6-14 is an aryl group, The compound according to the above [1] or a pharmaceutically acceptable salt thereof. [3]R 1 and R 2 together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe):

[0014] [ka]

[0015] (Wherein Rx and Ry each independently represent an oxo group, C 6-14 C optionally substituted with an aryloxy group or a hydroxyl group 1-6 alkyl group, wherein two Rx and two Ry are each independently joined together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; Rz is a hydrogen atom or C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3; (wherein n1 is preferably an integer of 0 to 2, more preferably 0, and n2 is preferably 0 or 1.) or R 1and R 2 are each independently 1-6 C optionally substituted with an alkoxy group 1-6 is an alkyl group; fR 3 are each independently 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), C 6-14 Aryl group, 5- to 8-membered aromatic heterocyclic group, -OR c1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R 3a is a hydrogen atom or C 1-6 represents an alkyl group; A is a divalent C optionally substituted with a hydroxyl group 3-14 a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; Q is C 1-6 Alkyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R 4 (where R 4 are each independently 1-6 Alkoxy group, C 6-14 Aryl-C 1-6 C optionally substituted with a group selected from an alkoxy group, a hydroxyl group, and a halogen atom 1-6 Alkyl group, C 1-6 5- to 8-membered aromatic heterocyclic group optionally substituted with an alkyl group, a nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group), or -COR e (R e is C 1-6 (Alkyl group) may be substituted with; M 1 is C 1-6 Alkyl group or C 6-14 C optionally substituted with an aryl group 1-4 Alkylene group R a1 ~R a3 , and R b1 ~R b3 are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 Alkyl group, C 2-8 Alkynyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group); R c1 ~R c3 are each independently a hydrogen atom, C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group), or C 6-14 is an aryl group, The compound according to the above [1] or [2] or a pharmaceutically acceptable salt thereof.

[0016] [4](1)1)g indicates 1; 2)(i)M 1 may be substituted C 2-4 Indicates an alkylene group; (ii) M 1 is -(CH2)-, and A represents an optionally substituted divalent non-aromatic hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; or (iii)M 1 is -(CH2)-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 is optionally substituted with (as described in [1] above); or (2)1) g indicates 0; 2)(i)M 1 may be substituted C 2-4 Indicates an alkylene group; (ii) M 1 is -(CH2)-, and Q is C 1-6 alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 is optionally substituted with (as described in [1] above); or (iii)M 1 is -(CH2)-, Q represents an aromatic hydrocarbon ring group, and the group is the same or different and is composed of 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (Rc3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or -COR e (R e may be substituted C 1-6 It may be substituted with an alkyl group; R a2 ~R a3 , and R b2 ~R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8 an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or -COR f (R f is C 1-6 an alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group), and R c2 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 an alkyl group, or an optionally substituted aryl group; The compound according to the above [1] or a pharmaceutically acceptable salt thereof.

[0017] The compound described in the above [4] or a pharmaceutically acceptable salt thereof corresponds to the compound described in the following [4A] or a pharmaceutically acceptable salt thereof. [4A] Formula (I) below:

[0018] [ka]

[0019] [In the formula, R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form the following formulae (IIa) to (IIe):

[0020] [ka]

[0021] (In the formula, Rx and Ry each independently represent an oxo group, an optionally substituted aryloxy group, or an optionally substituted C 1-6 represents an alkyl group, wherein two Rx and two Ry may each independently be joined together with the carbon atom to which they are attached to form a heterocycloalkane or a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 represents an alkyl group; n1 and n2 each independently represent an integer of 0 to 3; (wherein n1 is preferably an integer of 0 to 2, more preferably 0, and n2 is preferably 0 or 1) or R 1 and R 2 each independently represents an optionally substituted C 1-6 represents an alkyl group; fR 3 are each independently 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R3a is a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; (1)1)g indicates 1, 2)(i)M 1 may be substituted C 2-4 represents an alkylene group; M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO-, -(CH2) j4 -CO-(CH2) j5 -, -(CH2) j6 -CH(R)-(CH2) j7 -, -(CH2) j8 -S-(CH2) j9 -, or -NR a6 - (wherein R represents a hydroxyl group or an aryl group, R a4 ~R a6 is as described below, and j1 to j9 each independently represent an integer of 0 to 4; A represents an optionally substituted divalent hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R 4 each independently represents an optionally substituted C 1-6Alkyl group, optionally substituted aromatic heterocyclic group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or -COR e (R e may be substituted C 1-6 alkyl group); (ii) M 1 is -(CH2)-; M 2 is as previously described; A represents an optionally substituted divalent non-aromatic hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R 4 is optionally substituted with (as defined above); or (iii)M 1 is -(CH2)-; M 2 is as previously described; A represents an optionally substituted divalent aromatic hydrocarbon ring group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and has 1 to 3 R 4 (R 4is optionally substituted with (as defined above); or (2)1)g indicates 0; 2)(i)M 1 may be substituted C 2-4 represents an alkylene group; M 2 is as previously described; and, Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R 4 may be substituted with (as defined above); (ii) M 1 is -(CH2)-; M 2 is as previously described; and, Q is C 1-6 alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and has 1 to 3 R 4 (R 4 is optionally substituted with (as defined above); or (iii)M 1 is -(CH2)-; M 2 is as previously described; and Q represents an aromatic hydrocarbon ring group, and the group may be the same or different and may be composed of 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or -COR e (R e may be substituted C 1-6 and R a1 ~R a6 , and R b1 ~R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8 an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or -COR f (R f is C 1-6 alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group; R c1 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 It represents an optionally substituted alkyl group, or an optionally substituted aryl group. or a pharmaceutically acceptable salt thereof.

[0022] [5]R 1 and R 2 taken together with the nitrogen atom to which they are attached, form the following formula (IIa):

[0023] [ka]

[0024] (wherein Rx is C optionally substituted with a hydroxyl group) 1-6alkyl group, where two Rx together with the carbon atom to which they are attached form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; n1 represents an integer of 0 to 3; (wherein n1 is preferably an integer of 0 to 2, more preferably 0). forming a group represented by A compound according to any one of the above [1], [2], [3], [4], and [4A], or a pharmaceutically acceptable salt thereof.

[0025] [6](1)g indicates 1; (2)(i)M 1 may be substituted C 2-4 Indicates an alkylene group; (ii) M 1 is -(CH2)-, and A represents an optionally substituted divalent non-aromatic hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; or (iii)M 1 is -(CH2)-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 may be substituted with (as described in [1] above); The compound according to any one of the above [1], [4], [4A] and [5], or a pharmaceutically acceptable salt thereof. [7] g is 1; fR 3 are each independently -OR c1 (R c1 as described below); f represents an integer of 0 to 3; R 3a is a hydrogen atom or C1-6 represents an alkyl group; A is C 3-8 Cycloalkylene group, C 3-8 Cycloalkenylene group, C 6-14 an arylene group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; Q is C 3-8 Cycloalkyl group or C 6-14 aryl groups, each of which may be the same or different and which is 1 to 3 R 4 (where R 4 are each independently 1-6 Alkoxy group, C 6-14 Aryl-C 1-6 C optionally substituted with an alkoxy group, a hydroxyl group, or a halogen atom 1-6 Alkyl group; Nitro group; -NR a2 R b2 (R a2 and R b2 as described below);-OR c2 (R c2 (as described below);-CO2R c3 (R c3 (See below);-CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group); a cyano group; or a halogen atom); M 1 is -(CH2) i - (wherein i represents 1 to 4); M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO- or -(CH2) j4 -CO-(CH2)j5 -(In the formula, R a4 ~R a5 is as described below, and j1 to j5 each independently represent an integer of 0 to 4; R a2 ~R a5 , and R b2 ~R b3 are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 Alkyl group, C 2-8 Alkynyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group); R c1 ~R c3 are each independently a hydrogen atom, C 1-6 Alkyl group or -COR h (R h is C 1-6 alkyl group), A compound according to any one of the above [1], [2], [3], [4], [4A], [5] or [6], or a pharmaceutically acceptable salt thereof. [8]R 1 and R 2 taken together with the nitrogen atom to which they are attached, form the following formula (IIa):

[0026] [ka]

[0027] (wherein n1 represents 0) forming a group represented by The compound according to the above [7] or a pharmaceutically acceptable salt thereof. [9](1) g indicates 0; (2)(i)M 1 may be substituted C 2-4Indicates an alkylene group; (ii) M 1 is -(CH2)-, and Q is C 1-6 alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 is optionally substituted with (as described in [1] above); or (iii)M 1 is -(CH2)-, Q represents an aromatic hydrocarbon ring group, and the group is the same or different and is composed of 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or -COR e (R e may be substituted C 1-6 It may be substituted with an alkyl group; R a2 ~R a3 , and R b2 ~R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or -COR f (R f is C 1-6 an alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group), and R c2 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 an alkyl group, or an optionally substituted aryl group; The compound according to any one of the above [1], [4], [4A], and [5], or a pharmaceutically acceptable salt thereof.

[10] g is 0; fR 3 But, -OR c1 (R c1 is as described below); f is an integer from 0 to 3; Q is C 1-6 Alkyl group, C 3-14 Cycloalkyl groups, C 6-14 an aryl group or a 5- to 14-membered spirocyclic group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 are each independently C 1-6 Alkyl group, -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group), or -COR e (R e is C 1-6optionally substituted with alkyl groups); M 1 But C 1-6 C optionally substituted with alkyl group 1-4 represents an alkylene group; M 2 But -(CH2) j1 -or-(CH2) j2 -O-(CH2) j3 - (wherein j1 to j3 each independently represent an integer of 0 to 4); R a3 , and R b3 are each independently a hydrogen atom or C 3-8 represents a cycloalkyl group, and R c1 ~R c3 are each independently a hydrogen atom or C 1-6 The compound according to any one of the above [1], [2], [3], [4], [4A], [5] or [9], wherein the alkyl group is an alkyl group, or a pharmaceutically acceptable salt thereof.

[11] R 1 and R 2 taken together with the nitrogen atom to which they are attached, form the following formula (IIa):

[0028] [ka]

[0029] (wherein n1 represents 0) forming a group represented by The compound according to the above

[10] or a pharmaceutically acceptable salt thereof.

[12] g is 1; fR 3 But, -OR c1 (R c1 is a hydrogen atom or -COR h (R h is C 1-6 alkyl group); f is 0 or 1; R 3a is a hydrogen atom or C1-6 is an alkyl group; A is C 3-8 is a cycloalkylene group; Q is C 6-14 aryl groups, each of which may be the same or different and may have 1 to 3 R 4 (where R 4 are each independently C 1-6 Alkoxy group, C 6-14 Aryl-C 1-6 C optionally substituted with an alkoxy group, a hydroxyl group, or a halogen atom 1-6 alkyl groups; -NR a2 R b2 (R a2 and R b2 are each independently a hydrogen atom, C 1-6 Alkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl groups); -CO2R c3 (R c3 is C 1-6 alkyl group); -CONR a3 R b3 (R a3 and R b3 are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 Alkyl group, C 2-8 Alkynyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group; or (indicating halogen atoms) may be substituted with; M 1 is -(CH2)i - (wherein i is 1 to 4); M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 - (wherein j1 to j3 each independently represent an integer of 0 to 4). The compound according to the above [8] or a pharmaceutically acceptable salt thereof.

[13] g is 0; fR 3 is a hydroxyl group; f is an integer of 0 or 1; R 3a is a hydrogen atom; Q is C 3-14 Cycloalkyl groups, C 6-14 an aryl group or a 5- to 14-membered spirocyclic group; M 1 But C 1-6 C optionally substituted with alkyl group 1-4 is an alkylene group; M 2 But -(CH2) j1 - (wherein j1 represents 0) The compound according to the above

[11] or a pharmaceutically acceptable salt thereof.

[14] The compound represented by formula (I) is one or more compounds selected from the group of compounds represented by the following structural formulas: The compound according to any one of the above [1] to

[13] or a pharmaceutically acceptable salt thereof.

[0030] [ka]

[0031] [ka]

[0032] [ka]

[0033] [ka]

[0034] [ka]

[0035] [ka]

[0036] [ka]

[0037] [ka]

[0038]

[15] g is 1; f is 0; R 3a is a hydrogen atom; A is C 3-8 is a cycloalkylene group; Q is C 6-14 aryl groups, each of which may be the same or different and may have 1 to 3 R 4 (where R 4 -CONR a3 R b3 (R a3 and R b3 together with the nitrogen atom to which they are attached form a 3- to 8-membered heterocycloalkyl group) may be substituted with; M 1 is -(CH2) i - (wherein i is 1 to 4); M 2 is -(CH2)j1 -or-(CH2) j2 -O-(CH2) j3 - (wherein j1 to j3 each independently represent an integer of 0 to 4). The compound according to the above

[12] or a pharmaceutically acceptable salt thereof.

[16] g is 0; f is 0; R 3a is a hydrogen atom; Q is a 5- to 14-membered spirocyclic group; M 1 But C 1-4 is an alkylene group; M 2 But -(CH2) j1 - (wherein j1 represents 0) That is, The compound according to the above

[13] or a pharmaceutically acceptable salt thereof.

[0039]

[17] A medicine comprising, as an active ingredient, the compound according to any one of the above [1] to

[16] or a pharmaceutically acceptable salt thereof.

[18] The pharmaceutical agent according to

[17] above, which is an autophagy function activator.

[19] The pharmaceutical agent according to

[17] above, which is a preventive or therapeutic agent for a disease caused by a decrease in autophagy function or a disease whose pathology is suppressed or improved by an increase in autophagy function.

[20] The pharmaceutical agent according to

[17] above, which is a preventive or therapeutic agent for neurodegenerative diseases; cardiovascular diseases; musculoskeletal diseases; skeletal diseases; lung diseases; kidney diseases; metabolic syndromes; liver lesions; immune, inflammatory and immune-related diseases; eye diseases; reproductive system dysfunction; congenital multisystem disorders; and / or cancer.

[21] A method for activating autophagy in a mammal, comprising administering to the mammal an effective amount of the compound according to any one of [1] to

[16] above or a pharmaceutically acceptable salt thereof.

[22] A method for preventing or treating a disease caused by a decrease in autophagy function in a mammal in need thereof, or a disease whose pathology is suppressed or ameliorated by enhancement of autophagy function, comprising administering to the mammal an effective amount of the compound according to any of [1] to

[16] above or a pharmaceutically acceptable salt thereof.

[23] The method for preventing or treating a disease caused by a decrease in autophagy function or a disease whose pathology can be suppressed or improved by enhancing autophagy function is neurodegenerative disease; cardiovascular disease; musculoskeletal disease; skeletal disease; lung disease; kidney disease; metabolic syndrome; liver lesion; immune, inflammatory, and immune-related disease; eye disease; reproductive system dysfunction; congenital multisystem disorder; and / or cancer.

[24] The compound according to any one of [1] to

[16] above, or a pharmaceutically acceptable salt thereof, used for activating autophagy function.

[25] The compound according to any one of [1] to

[16] above, or a pharmaceutically acceptable salt thereof, for use in the prevention or treatment of a disease caused by a decrease in autophagy function or a disease whose pathology can be suppressed or improved by enhancing autophagy function.

[26] The compound according to

[25] above, or a pharmaceutically acceptable salt thereof, wherein the disease caused by a decrease in autophagy function or the disease whose pathology can be suppressed or improved by an increase in autophagy function is neurodegenerative disease; cardiovascular disease; musculoskeletal disease; skeletal disease; lung disease; kidney disease; metabolic syndrome; liver lesion; immune, inflammatory and immune-related disease; eye disease; reproductive system dysfunction; congenital multisystem disorder; and / or cancer.

[27] Use of the compound according to any one of the above [1] to

[16] or a pharmaceutically acceptable salt thereof for the manufacture of an autophagy function activator.

[28] Use of the compound according to any one of [1] to

[16] above or a pharmaceutically acceptable salt thereof for the manufacture of an agent for preventing or treating a disease caused by a decrease in autophagy function or a disease whose pathology is suppressed or ameliorated by an increase in autophagy function.

[29] The use described in

[28] above, wherein the disease caused by decreased autophagy function or the disease whose pathology can be suppressed or improved by increasing autophagy function is neurodegenerative disease; cardiovascular disease; musculoskeletal disease; skeletal disease; lung disease; kidney disease; metabolic syndrome; liver lesion; immune, inflammatory and immune-related disease; eye disease; reproductive system dysfunction; congenital multisystem disorder; and / or cancer. [Effects of the Invention]

[0040] The present invention provides, as one embodiment, a compound that has the effect of activating autophagy function and is useful as a preventive or therapeutic agent for diseases caused by decreased autophagy function or diseases whose pathology can be suppressed or ameliorated by enhancing autophagy function. DETAILED DESCRIPTION OF THE INVENTION

[0041] The present invention will be described in detail below based on the embodiments, but the present invention is not limited thereto. Those skilled in the art may modify the embodiments of the present invention in various aspects without departing from the spirit of the present invention, and such modifications are also included within the scope of the present invention. Unless otherwise defined in context, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. Although any methods and materials similar or equivalent to those described herein can be used in the practice or testing of the present invention, the preferred methods and materials are described below. All publications and patents mentioned herein are incorporated by reference for the purpose of describing and disclosing, for example, the constructs and methodology described in the publications that might be used in connection with the described invention.

[0042] The definitions of each group used in this specification are described in detail below. Unless otherwise specified, each group has the following definition.

[0043] In this specification, "C a-b ” (e.g., C 1-6 ) or "Ca -C b " (for example, C1-C6) indicates that the number of carbon atoms constituting the group is a to b (for example, 1 to 6).

[0044] In the present specification, examples of the "halogen atom" include fluorine, chlorine, bromine and iodine.

[0045] In this specification, "C 1-6 Examples of the alkyl (group) include methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, 1-ethylpropyl, hexyl, isohexyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethylbutyl, and 2-ethylbutyl.

[0046] In this specification, "C 2-6 Examples of the "alkenyl (group)" include ethenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 3-methyl-2-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 4-methyl-3-pentenyl, 1-hexenyl, 3-hexenyl, and 5-hexenyl.

[0047] In this specification, "C 2-8 Examples of the alkynyl (group) include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 4-methyl-2-pentynyl, 6-heptynyl, 7-octynyl, and the like.

[0048] In this specification, "C 1-6 Examples of the alkoxy (group) include methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, pentyloxy, hexyloxy, and the like.

[0049] As used herein, the term "hydrocarbon ring" includes aromatic and non-aromatic rings formed with carbon atoms as ring-constituting atoms, such as aromatic hydrocarbon rings and non-aromatic hydrocarbon rings (cycloalkanes, cycloalkenes), etc. As used herein, "non-aromatic" encompasses both non-aromatic and anti-aromatic rings according to Hückel's rule.

[0050] In the present specification, examples of the "aromatic hydrocarbon ring" include benzene, naphthalene, etc., and preferably C 6-14 Examples include aromatic hydrocarbon rings.

[0051] In the present specification, examples of "cycloalkane" include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, etc., and preferably C 3-14 Cycloalkanes are preferred, and C 3-8 Examples include cycloalkanes.

[0052] In the present specification, examples of "cycloalkene" include cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, etc., and preferably C 3-14 Cycloalkene is preferred, and C 3-8 Cycloalkenes are examples.

[0053] As used herein, the term "hydrocarbon ring" includes bridged cyclic hydrocarbons in which a bridge bond is formed within the ring. Examples of such bridged cyclic hydrocarbons include bicyclo[2.2.1]heptane, bicyclo[3.2.1]octane, bicyclo[5.2.0]nonane, and adamantane.

[0054] As used herein, the term "hydrocarbon ring" includes bicyclic rings formed by a spiro bond between the same or different hydrocarbon rings ("spiro rings"). Such a "spiro ring" may contain, in addition to carbon atoms as ring-constituting atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom. Examples include 5- to 14-membered spiro rings such as spiro[3.3]heptane, spiro[5.5]undecane, 3-oxaspiro[5.5]undecane, 2-azaspiro[3.3]heptane, 6-azaspiro[2.5]octane, 2-azaspiro[3.5]nonane, 7-azaspiro[3.5]nonane, and 3-azaspiro[5.5]undecane; more specifically, a 5- to 14-membered spirohydrocarbon ring or a 5- to 14-membered spirohydrocarbon ring containing 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom (preferably a 7- to 12-membered spirohydrocarbon ring or a 7- to 12-membered spirohydrocarbon ring containing 1 to 3 oxygen atoms).

[0055] In the present specification, the term "hydrocarbon ring group" refers to a monovalent group having one bond derived from the above-mentioned "hydrocarbon ring", and C 3-14 Preferred examples of hydrocarbon ring groups include non-aromatic hydrocarbon ring groups such as cycloalkyl (groups), cycloalkenyl (groups), and spiro ring groups derived from the above-mentioned spiro rings, and aromatic hydrocarbon ring groups such as aryl (groups).

[0056] In the present specification, the term "cycloalkyl (group)" is preferably "C 3-14 and cycloalkyl (group)" such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, bicyclo[3.2.1]octyl, adamantyl, and the like.

[0057] In the present specification, the "cycloalkenyl (group)" is preferably "C 3-14and cycloalkenyl (group)" such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, and the like.

[0058] In the present specification, the term "aryl (group)" is preferably "C 6-14 Aryl (group)" and examples thereof include phenyl, 1-naphthyl, 2-naphthyl, 1-anthryl, 2-anthryl, 9-anthryl, etc. More preferably, C 6-14 The aryl group is more preferably C 6-10 Examples include aryl (groups).

[0059] In this specification, the term "divalent hydrocarbon ring group" refers to a divalent group having two bonds derived from the above-mentioned "hydrocarbon ring." Specific examples include divalent non-aromatic hydrocarbon ring groups such as cycloalkylene (groups) and cycloalkenylene (groups), and divalent aromatic hydrocarbon ring groups such as arylene (groups). In the present specification, the "cycloalkylene (group)" is preferably "C 3-14 and cycloalkylene (group)" such as cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, bicyclo[2.2.1]heptylene, bicyclo[2.2.2]octylene, bicyclo[3.2.1]octylene, adamantylene, and the like. As used herein, the term "cycloalkenylene (group)" is preferably "C 3-14 and cycloalkenylene (group)" such as cyclopropenylene, cyclobutenylene, cyclopentenylene, cyclohexenylene, cycloheptenylene, cyclooctenylene, and the like. In the present specification, the "arylene (group)" is preferably "C 6-14 arylene (group)" and examples thereof include phenylene, 1-naphthylene, 2-naphthylene, 1-anthrylene, 2-anthrylene, and 9-anthrylene. More preferably, C 6-10 Examples include arylene (groups).

[0060] In the present specification, the term "heterocycle" includes, for example, an aromatic heterocycle and a non-aromatic heterocycle each containing, as ring-constituting atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom. In the present specification, "non-aromatic" includes both non-aromatic and anti-aromatic rings according to Hückel's rule.

[0061] As used herein, examples of the "aromatic heterocycle" include 5- to 14-membered (preferably 5- to 10-membered, more preferably 5- to 8-membered) aromatic heterocycles containing, as ring-constituting atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom. Preferable examples of the "aromatic heterocycle" include 5- or 6-membered monocyclic aromatic heterocycles such as thiophene, furan, pyrrole, imidazole, pyrazole, thiazole, isothiazole, oxazole, isoxazole, pyridine, pyrazine, pyrimidine, pyridazine, 1,2,4-oxadiazole, 1,3,4-oxadiazole, 1,2,4-thiadiazole, 1,3,4-thiadiazole, triazole, tetrazole, and triazine; Benzothiophene, benzofuran, benzimidazole, benzoxazole, benzisoxazole, benzothiazole, benzisothiazole, benzotriazole, imidazopyridine, thienopyridine, furopyridine, pyrrolopyridine, pyrazolopyridine, oxazolopyridine, thiazolopyridine, imidazopyrazine, imidazopyrimidine, thienopyrimidine, furopyrimidine, pyrrolopyrimidine, pyrazolopyrimidine, oxazolopyrimidine, thiazolopyrimidine, pyrazolopyrimidine condensed aromatic heterocycles such as phenylmidine, pyrazolotriazine, naphtho[2,3-b]thiophene, phenoxathiin, indole, isoindole, 1H-indazole, purine, isoquinoline, quinoline, phthalazine, naphthyridine, quinoxaline, quinazoline, cinnoline, carbazole, β-carboline, phenanthridine, acridine, phenazine, phenothiazine, and phenoxazine, more specifically, 8- to 14-membered condensed polycyclic (preferably bicyclic or tricyclic) aromatic heterocycles.

[0062] As used herein, examples of the "non-aromatic heterocycle" include 3- to 14-membered (preferably 3- to 10-membered, more preferably 3- to 8-membered) non-aromatic heterocycles containing, as ring-constituting atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom. Preferable examples of the "non-aromatic heterocycle" include 3- to 8-membered monocyclic non-aromatic heterocycles such as aziridine, oxirane, thiirane, azetidine, oxetane, thietane, tetrahydrothiophene, tetrahydrofuran, pyrroline, pyrrolidine, imidazoline, imidazolidine, oxazoline, oxazolidine, pyrazoline, pyrazolidine, thiazoline, thiazolidine, tetrahydroisothiazole, tetrahydrooxazole, tetrahydroisoxazole, piperidine, piperazine, tetrahydropyridine, dihydropyridine, dihydrothiopyran, tetrahydropyrimidine, tetrahydropyridazine, dihydropyran, tetrahydropyran, tetrahydrothiopyran, morpholine, thiomorpholine, azepane, diazepane, azepine, azocane, diazocane, oxepane, and oxazepane; Examples of the heterocyclic ring include fused non-aromatic heterocycles such as dihydrobenzofuran, dihydrobenzimidazole, dihydrobenzoxazole, dihydrobenzothiazole, dihydrobenzisothiazole, dihydronaphtho[2,3-b]thiophene, tetrahydroisoquinoline, tetrahydroquinoline, 4H-quinolizine, indoline, isoindoline, tetrahydrothieno[2,3-c]pyridine, tetrahydrobenzazepine, tetrahydroquinoxaline, tetrahydrophenanthridine, hexahydrophenothiazine, hexahydrophenoxazine, tetrahydrophthalazine, tetrahydronaphthyridine, tetrahydroquinazoline, tetrahydrocinnoline, tetrahydrocarbazole, tetrahydro-β-carboline, tetrahydroacridine, tetrahydrophenazine, tetrahydrothioxanthene, and octahydroisoquinoline, and more specifically, 9- to 14-membered fused polycyclic (preferably bi- or tricyclic) non-aromatic heterocycles. In the present specification, the term "heterocycloalkane" refers to a saturated ring among the above-mentioned monocyclic non-aromatic heterocycles, and preferably includes those having 3 to 8 members. In the present specification, the term "nitrogen-containing heterocycle" includes "heterocycles" that contain at least one nitrogen atom as a ring-constituting atom.

[0063] In the present specification, examples of the "heterocyclic group" include (i) an aromatic heterocyclic group, (ii) a non-aromatic heterocyclic group, and (iii) a 6- to 10-membered bridged heterocyclic group, each of which contains, as ring-constituting atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom.

[0064] In the present specification, examples of the "aromatic heterocyclic group" (including "5- to 14-membered aromatic heterocyclic group") include 5- to 14-membered (preferably 5- to 10-membered, more preferably 5- to 8-membered) aromatic heterocyclic groups containing, as ring-constituting atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom. Preferable examples of the "aromatic heterocyclic group" include 5- or 6-membered monocyclic aromatic heterocyclic groups such as thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, triazolyl, tetrazolyl, and triazinyl; benzothiophenyl, benzofuranyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, benzotriazolyl, imidazopyridinyl, thienopyridinyl, furopyridinyl, pyrrolopyridinyl, pyrazolopyridinyl, oxazolopyridinyl, thiazolopyridinyl, imidazopyrazinyl, imidazopyrimidinyl, thienopyrimidinyl, furopyrimidinyl, pyrrolopyrimidinyl, pyrazolopyrimidinyl, oxazolopyrimidinyl, thiazolopyrimidinyl, Examples of fused aromatic heterocyclic groups include pyrazolotriazinyl, naphtho[2,3-b]thienyl, phenoxathiinyl, indolyl, isoindolyl, 1H-indazolyl, purinyl, isoquinolyl, quinolyl, phthalazinyl, naphthyridinyl, quinoxalinyl, quinazolinyl, cinnolinyl, carbazolyl, β-carbolinyl, phenanthridinyl, acridinyl, phenazinyl, phenothiazinyl, and phenoxazinyl, and more specifically include 8- to 14-membered fused polycyclic (preferably bicyclic or tricyclic) aromatic heterocyclic groups.

[0065] In the present specification, examples of the "non-aromatic heterocyclic group" (including "3- to 14-membered non-aromatic heterocyclic group") include 3- to 14-membered (preferably 4- to 10-membered) non-aromatic heterocyclic groups containing, as ring-constituting atoms other than carbon atoms, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom and an oxygen atom. Preferable examples of the "non-aromatic heterocyclic group" include aziridinyl, oxiranyl, thiiranyl, azetidinyl, oxetanyl, thietanyl, tetrahydrothienyl, tetrahydrofuranyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, oxazolidinyl, pyrazolinyl, pyrazolidinyl, thiazolinyl, thiazolidinyl, tetrahydroisothiazolyl, tetrahydrooxazolyl, tetrahydroisoisothiazolyl, tetrahydroiso ... 3- to 8-membered monocyclic non-aromatic heterocyclic groups such as xazolyl, piperidinyl, piperazinyl, tetrahydropyridinyl, dihydropyridinyl, dihydrothiopyranyl, tetrahydropyrimidinyl, tetrahydropyridazinyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, azepanyl, diazepanyl, azepinyl, oxepanyl, azocanyl, diazocanyl, and oxazepanyl; Dihydrobenzofuranyl, dihydrobenzimidazolyl, dihydrobenzoxazolyl, dihydrobenzothiazolyl, dihydrobenzisothiazolyl, dihydronaphtho[2,3-b]thienyl, tetrahydroisoquinolyl, tetrahydroquinolyl, 4H-quinolidinyl, indolinyl, isoindolinyl, tetrahydrothieno[2,3-c]pyridinyl, tetrahydrobenzazepinyl, tetrahydroquinoxalinyl, tetrahydrophenanthridinyl, hexahydrophenothiazolyl tetrahydro-, hexahydrophenoxazinyl, tetrahydrophthalazinyl, tetrahydronaphthyridinyl, tetrahydroquinazolinyl, tetrahydrocinnolinyl, tetrahydrocarbazolyl, tetrahydro-β-carbolinyl, tetrahydroacridinyl, tetrahydrophenazinyl, tetrahydrothioxanthenyl, octahydroisoquinolyl, and the like, more specifically, 9- to 14-membered fused polycyclic (preferably bi- or tricyclic) non-aromatic heterocyclic groups.

[0066] In the present specification, the term "divalent aromatic heterocyclic group" refers to a divalent group having two bonds derived from the above-mentioned "aromatic heterocycle". Suitable examples include divalent groups having two bonds derived from a fused polycyclic (preferably bicyclic or tricyclic) aromatic heterocycle, and preferably divalent groups having two bonds derived from an 8- to 14-membered nitrogen-containing fused aromatic heterocycle (e.g., indole-diyl).

[0067] In this specification, the term "heterocycloalkyl (group)" refers to a saturated group from the above-mentioned monocyclic non-aromatic heterocyclic groups, preferably 3- to 8-membered groups.

[0068] In the present specification, the "heterobridged ring group" includes a "6- to 10-membered heterobridged ring group", and preferable examples thereof include quinuclidinyl, 7-azabicyclo[2.2.1]heptanyl, 3-azabicyclo[3.1.0]hexanyl, 6-oxa-3-azabicyclo[3.1.0]hexanyl, 3-azabicyclo[3.1.1]heptanyl, 6-oxa-3-azabicyclo [3.1.1]heptanyl, 2-azabicyclo[2.2.1]heptanyl, 2-oxa-5-azabicyclo[2.2.1]heptanyl, 3-azabicyclo[3.2.1]octanyl, 8-oxa-3-azabicyclo[3.2.1]octanyl, 8-azabicyclo[3.2.1]octanyl, and 3-oxa-8-azabicyclo[3.2.1]octanyl.

[0069] In the present specification, the term "nitrogen-containing heterocyclic group" includes "heterocyclic groups" that contain at least one nitrogen atom as a ring-constituting atom.

[0070] In this specification, the term "heterocycloalkylene (group)" refers to a divalent group having two bonds derived from a saturated group, "heterocycloalkane," among the above-mentioned monocyclic non-aromatic heterocyclic groups. Preferably, 3- to 8-membered groups are used. Examples thereof include nitrogen-containing groups such as piperidine-diyl and piperazine-diyl.

[0071] As used herein, "optionally substituted C 1-6 Examples of the "substituent" in the "optionally substituted group or ring" in the definition of the compound represented by formula (I) (hereinafter referred to as compound (I)), such as "alkyl group" or "optionally substituted aromatic heterocyclic group", include substituents selected from the following [Substituent group A]. The "substituents" can be present in 1 to 5 (preferably 1 to 3) substitutable positions, and when the number of substituents is 2 or more, the respective substituents may be the same or different. In addition, when a special explanation is given about the "substituent" of each group or ring, etc., that explanation shall be followed.

[0072] [Substituent group A] (1) a halogen atom, (2) a nitro group, (3) a cyano group, (4) an oxo group, (5) a hydroxy group, (6) an optionally halogenated C1-C6 alkoxy group (e.g., methoxy, chloromethoxy, trifluoroethoxy), (7) C6-C 14 aryloxy groups (e.g., phenoxy, naphthoxy); (8) C7-C 16 aralkyloxy groups (e.g., benzyloxy), (9) C1-C6 alkyl-carbonyloxy group (e.g., acetoxy, propanoyloxy), (10) C6-C 14 aryl-carbonyloxy groups (e.g., benzoyloxy, 1-naphthoyloxy, 2-naphthoyloxy); (11) C1-C6 alkoxy-carbonyloxy groups (e.g., methoxycarbonyloxy, ethoxycarbonyloxy, propoxycarbonyloxy, butoxycarbonyloxy), (12) 5- to 14-membered aromatic heterocyclic groups (e.g., thienyl, furyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl), wherein 5- to 6-membered monocyclic aromatic heterocyclic groups are preferred, and 5- to 6-membered monocyclic nitrogen-containing aromatic heterocyclic groups are more preferred. (13) 3- to 14-membered non-aromatic heterocyclic groups (e.g., aziridinyl, oxiranyl, thiiranyl, diazirinyl, azetidinyl, oxetanyl, thietanyl, tetrahydrothienyl, tetrahydrofuranyl, pyrrolinyl, pyrrolidinyl, imidazolinyl, imidazolidinyl, oxazolinyl, oxazolidinyl, pyrazolinyl, pyrazolidinyl, thiazolinyl, thiazolidinyl, tetrahydroisothiazolyl, tetrahydrooxazolyl, tetrahydroisoxazolyl, piperidinyl, piperazinyl, tetrahydropyri dihydropyridinyl, dihydrothiopyranyl, tetrahydropyrimidinyl, tetrahydropyridazinyl, dihydropyranyl, tetrahydropyranyl, tetrahydrothiopyranyl, morpholinyl, thiomorpholinyl, azepanyl, diazepanyl, azepinyl, oxepanyl, azocanyl, diazocanyl, oxazepanyl), wherein a 3- to 8-membered monocyclic non-aromatic heterocyclic group is preferred, and a 3- to 8-membered monocyclic nitrogen-containing non-aromatic heterocyclic group or a 3- to 8-membered monocyclic oxygen-containing non-aromatic heterocyclic group is more preferred. (14) a formyl group, (15) a carboxy group, (16) an optionally halogenated C1-C6 alkyl-carbonyl group (e.g., acetyl, chloroacetyl, trifluoroacetyl), (17) C6-C 14 aryl-carbonyl groups (e.g., benzoyl, 1-naphthoyl, 2-naphthoyl); (18) C1-C6 alkoxy-carbonyl groups (e.g., methoxycarbonyl, ethoxycarbonyl), (19) a carbamoyl group, (20) an amino group, (21) mono- or di-C1-C6 alkylamino groups (e.g., methylamino, ethylamino, propylamino, isopropylamino, butylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, N-ethyl-N-methylamino), (22) Mono- or di-C6-C 14 arylamino groups (e.g., phenylamino); (23) formylamino group, (24) C1-C6 alkyl-carbonylamino group (e.g., acetylamino, propanoylamino, butanoylamino), (25) C1-C6 alkoxy-carbonylamino groups (e.g., methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, butoxycarbonylamino, tert-butoxycarbonylamino), (26) optionally halogenated C1-C6 alkyl groups (e.g., methyl, chloromethyl, difluoromethyl, trifluoromethyl, ethyl, 2-bromoethyl, 2,2,2-trifluoroethyl); (27) C2-C6 alkenyl groups (e.g., ethenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, 1-butenyl), (28) C2-C6 alkynyl groups (e.g., ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl), (29) C3-C 10 cycloalkyl groups (e.g., cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, bicyclo[2.2.1]heptyl, bicyclo[2.2.2]octyl, bicyclo[3.2.1]octyl, adamantyl); (30) C3-C 10 cycloalkenyl groups (e.g., cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl), (31) C6-C 14 aryl groups (e.g., phenyl, naphthyl); (32) (mono- or di-C1-C6 alkylamino)carbonyl group (e.g., methylamino-carbonyl group), and (33) C1-C6 alkyl-sulfonyl group (e.g., methylsulfonyl group).

[0073] Preferred embodiments of the groups represented by each symbol in the compound (I) represented by the formula (I) will be described below.

[0074] R 1 and R 2 is as defined above, but (1) In one preferred embodiment, the groups represented by the following formulae (IIa) to (IIe) are taken together with the nitrogen atom to which they are bonded:

[0075] [ka]

[0076] wherein Rx and Ry each independently represent an oxo group, an optionally substituted C 6-14 an aryloxy group or an optionally substituted C 1-6 alkyl group, wherein two Rx and two Ry are each independently joined together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or form a group represented by any of the following: In a more preferred embodiment, wherein Rx is optionally substituted C 1-6 alkyl group, where two Rx together with the carbon atom to which they are attached form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; Ry is an oxo group or an optionally substituted C 6-14 is an aryloxy group, Rz is a hydrogen atom or an optionally substituted C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or form a group represented by any of the following: In a more preferred embodiment, In the above formulas (IIa) to (IIe), (wherein Rx is C optionally substituted with a hydroxyl group) 1-6 alkyl group, where two Rx together with the carbon atom to which they are attached form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; Ry is an oxo group or C 6-14 is an aryloxy group; Rz is a hydrogen atom or C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. (wherein n1 is preferably an integer of 0 to 2, more preferably 0, and n2 is preferably 0 or 1) or form a group represented by any of the following: In a particularly preferred embodiment, Formula (IIa):

[0077] [ka]

[0078] (wherein Rx is C optionally substituted with a hydroxyl group) 1-6 alkyl group, where two Rx together with the carbon atom to which they are attached form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; n1 represents an integer between 0 and 3) (wherein n1 is preferably an integer of 0 to 2, more preferably 0). or an embodiment in which a group represented by (2) Another preferred embodiment is: R 1 and R 2 are each independently 1-6 C optionally substituted with an alkoxy group 1-6 An embodiment in which the group is an alkyl group is exemplified.

[0079] fR 3 is as defined above, but In a preferred embodiment, Independently, C 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), C 6-14 Aryl group, 5- to 8-membered aromatic heterocyclic group, -OR c1 (R c1 is a hydrogen atom, C 1-6 Alkyl group, or -COR h (R h is C 1-6 alkyl group), or a halogen atom; In a more preferred embodiment, -OR c1 (R c1 is a hydrogen atom, C 1-6 Alkyl group, or -COR h (R h is C 1-6 An example of such an alkyl group is as follows. f is as defined above, In a preferred embodiment, f is 0 or 1.

[0080] R 3a is as defined above, but In a preferred embodiment, it is a hydrogen atom.

[0081] A is as defined above, but In a preferred embodiment, Optionally substituted divalent C3-14 a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or an optionally substituted 3- to 8-membered heterocycloalkylene group; In a more preferred embodiment, Divalent C optionally substituted with a hydroxyl group 3-14 a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; In a more preferred embodiment, C 3-8 Cycloalkylene group, C 3-8 Cycloalkenylene group, C 6-14 Examples of embodiments include an arylene group, a divalent 8- to 14-membered fused aromatic heterocyclic group (more preferably a divalent 8- to 14-membered nitrogen-containing fused aromatic heterocyclic group), or a 3- to 8-membered heterocycloalkylene group.

[0082] g is as defined above.

[0083] (1) Q is as defined above, but In a preferred embodiment, C 1-6 Alkyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R 4 [where R 4 are each independently Optionally substituted C 1-6 alkyl groups; an optionally substituted 5- to 8-membered aromatic heterocyclic group; nitro group; -NR a2 R b2 (R a2 and R b2 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 3-8 a cycloalkyl group, an optionally substituted 3- to 8-membered heterocycloalkyl group, or -COR f (R fis C 1-6 Alkyl group, C 2-8 Alkynyl group, optionally substituted C 3-8 hydrocarbon ring group, or C 3-8 a heterocycloalkyl group; -OR c2 (R c2 is a hydrogen atom, optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group), or optionally substituted C 6-14 an aryl group); Halogen atoms; cyano groups; -CO2R c3 (R c3 is a hydrogen atom, optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group or optionally substituted C 6-14 an aryl group, -CONR a3 R b3 (R a3 and R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8 Alkynyl group, optionally substituted C 3-8 a hydrocarbon ring group, an optionally substituted 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 alkyl group, optionally substituted C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl), where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterobridged ring group), or -COR e (R e may be substituted C 1-6 alkyl group)] may be substituted with; More preferably, C 1-6 Alkyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R 4 [where R 4 are each independently C 1-6 Alkoxy group, C 6-14 Aryl-C 1-6 C optionally substituted with a group selected from an alkoxy group, a hydroxyl group, and a halogen atom 1-6 alkyl groups; C 1-6 a 5- to 8-membered aromatic heterocyclic group optionally substituted by an alkyl group; nitro group; -NR a2 R b2 (R a2 and R b2 are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 Alkyl group, C 2-8 Alkynyl group, C 3-8 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 a heterocycloalkyl group; -OR c2 (R c2 is a hydrogen atom, C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group) or C 6-14 an aryl group); Halogen atoms; cyano groups; -CO2R c3 (R c3 is a hydrogen atom, C 1-6 Alkyl group, -COR h (Rh is C 1-6 Alkyl group, or C 6-14 an aryl group); -CONR a3 R b3 (R a3 and R b3 are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 Alkyl group, C 2-8 Alkynyl group, C 3-8 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl), where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterobridged ring group), or -COR e (R e may be substituted C 1-6 alkyl group) An embodiment in which the group may be substituted with (2) Another preferred embodiment of Q is C 3-8 Cycloalkyl group or C 6-14 aryl groups, each of which may be the same or different and which is 1 to 3 R 4 [where R 4 are each independently C 1-6 Alkoxy group, C 6-14 Aryl-C 1-6 C optionally substituted with an alkoxy group, a hydroxyl group, or a halogen atom 1-6 alkyl groups; nitro group; -NR a2 R b2 (R a2 and R b2 are each independently a hydrogen atom, C1-6 C optionally substituted with an alkoxy group 1-6 Alkyl group, C 3-14 a cycloalkyl group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 Alkyl group, C 2-8 Alkynyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group); -OR c2 (R c2 is a hydrogen atom, C 1-6 Alkyl group or -COR h (R h is C 1-6 alkyl group); -CO2R c3 (R c3 is a hydrogen atom, C 1-6 Alkyl group or -COR h (R h is C 1-6 alkyl group); -CONR a3 R b3 (R a3 and R b3 are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 alkyl group, optionally substituted C 2-8 Alkynyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl), where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group); a cyano group; or indicates halogen atoms] An embodiment in which the group may be substituted with (3) Other preferred embodiments of Q include: C 1-6 Alkyl group, C 3-14 Cycloalkyl groups, C 6-14 an aryl group or a 5- to 14-membered spirocyclic group, each of which may be the same or different and has 1 to 3 R 4 [where R 4 are each independently C 1-6 alkyl groups, -OR c2 (R c2 is a hydrogen atom or C 1-6 alkyl group), Halogen atoms, cyano groups, -CO2R c3 (R c3 is a hydrogen atom or C 1-6 alkyl group); -CONR a3 R b3 (R a3 and R b3 are each independently a hydrogen atom or C 3-8 is a cycloalkyl group, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group; or -COR e (R e is C 1-6 alkyl group)] An embodiment in which the group may be substituted with

[0084] M 1 is as defined above, but In one preferred embodiment, C 1-6 Alkyl group or C 6-14 C optionally substituted with an aryl group 1-4 An embodiment in which the alkylene group is used is exemplified. M 2 is as defined above, but In one preferred embodiment, -(CH2)j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO-, -(CH2) j4 -CO-(CH2) j5 - (In the formula, R a4 ~R a5 are each a hydrogen atom, and j1 to j5 each independently represent an integer of 0 to 4).

[0085] Particularly preferred specific examples of the compound (I) represented by the formula (I) include the following.

[0086] [Compound A-1] In formula (I), R 1 and R 2 together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe):

[0087] [ka]

[0088] wherein Rx and Ry each independently represent an oxo group, an optionally substituted C 6-14 an aryloxy group or an optionally substituted C 1-6 alkyl group, wherein two Rx and two Ry are each independently joined together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R 1 and R 2 each independently represents an optionally substituted C1-6 is an alkyl group; fR 3 are each independently 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), C 6-14 Aryl group, 5- to 8-membered aromatic heterocyclic group, -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R 3a is a hydrogen atom or C 1-6 represents an alkyl group; A is an optionally substituted divalent C 3-14 a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or an optionally substituted 3- to 8-membered heterocycloalkylene group; Q is C 1-6 Alkyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, optionally substituted 5- to 8-membered aromatic heterocyclic group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group), or -COR e (R e may be substituted C 1-6 (Alkyl group) may be substituted with; R a1 ~R a3 , and R b1 ~R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8 Alkynyl group, optionally substituted C 3-8 a hydrocarbon ring group, an optionally substituted 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 alkyl group, optionally substituted C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group); R c1 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group), or optionally substituted C 6-14 It is an aryl group. (however, (1) M 1 is -(CH2)-, g is 0, and M 2 Ga-(CH2) j1 - when j1 is 0 and Q is benzene R 4 is not a pyrazolyl group substituted with a methyl group. (2) M 1 is -(CH2)-, g is 1, A is benzene, and M 2 But -(CH2) j1 - when j1 is 0 and Q is pyrazole R 4is not a methyl group.) or a pharmaceutically acceptable salt thereof.

[0089] [Compound A-2] In formula (I), R 1 and R 2 together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe):

[0090] [ka]

[0091] (Wherein Rx and Ry each independently represent an oxo group, C 6-14 C optionally substituted with an aryloxy group or a hydroxyl group 1-6 alkyl group, wherein two Rx and two Ry are each independently joined together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; Rz is a hydrogen atom or C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. (wherein n1 is preferably an integer of 0 to 2, more preferably 0, and n2 is preferably 0 or 1) or R 1 and R 2 are each independently 1-6 C optionally substituted with an alkoxy group 1-6 is an alkyl group; fR 3 are each independently 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), C 6-14 Aryl group, 5- to 8-membered aromatic heterocyclic group, -ORc1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R 3a is a hydrogen atom or C 1-6 represents an alkyl group; A is a divalent C optionally substituted with a hydroxyl group 3-14 a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; Q is C 1-6 Alkyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R 4 (where R 4 are each independently 1-6 Alkoxy group, C 6-14 Aryl-C 1-6 C optionally substituted with a group selected from an alkoxy group, a hydroxyl group, and a halogen atom 1-6 Alkyl group, C 1-6 5- to 8-membered aromatic heterocyclic group optionally substituted with an alkyl group, a nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group), or -COR e (R e is C 1-6 (Alkyl group) may be substituted with; M1 is C 1-6 Alkyl group or C 6-14 C optionally substituted with an aryl group 1-4 is an alkylene group; R a1 ~R a3 , and R b1 ~R b3 are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 alkyl group, optionally substituted C 2-8 Alkynyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group); R c1 ~R c3 are each independently a hydrogen atom, C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group), or C 6-14 It is an aryl group. (however, (1) M 1 is -(CH2)-, g is 0, and M 2 Ga-(CH2) j1 - when j1 is 0 and Q is benzene R 4 is not a pyrazolyl group substituted with a methyl group. (2) M 1 is -(CH2)-, g is 1, A is benzene, and M 2 But -(CH2) j1 - when j1 is 0 and Q is pyrazole R 4 is not a methyl group.) The above [Compound A-1], which is: or a pharmaceutically acceptable salt thereof.

[0092] [Compound A-3] In formula (I), R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form the following formulae (IIa) to (IIe):

[0093] [ka]

[0094] (In the formula, Rx and Ry each independently represent an oxo group, an optionally substituted aryloxy group, or an optionally substituted C 1-6 represents an alkyl group, wherein two Rx and two Ry may each independently be joined together with the carbon atom to which they are attached to form a heterocycloalkane or a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 represents an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. (wherein n1 is preferably an integer of 0 to 2, more preferably 0, and n2 is preferably 0 or 1) or R 1 and R 2 each independently represents an optionally substituted C 1-6 represents an alkyl group; fR 3 are each independently 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R 3a is a hydrogen atom, C 1-6 Alkyl group, C 2-6 Alkenyl group, -COR g (R g is C 1-6 alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; (1)1)g indicates 1, 2)(i)M 1 may be substituted C 2-4 represents an alkylene group; M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO-, -(CH2) j4 -CO-(CH2) j5 -, -(CH2) j6 -CH(OH)-(CH2) j7 -, -(CH2) j8 -S-(CH2) j9 -, or -NR a6 - (In the formula, R a4 ~R a6 is as described below, and j1 to j9 each independently represent an integer of 0 to 4; A represents an optionally substituted divalent hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R 4 each independently represents an optionally substituted C 1-6 Alkyl group, optionally substituted aromatic heterocyclic group, nitro group, -NRa2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or -COR e (R e may be substituted C 1-6 alkyl group); (ii) M 1 is -(CH2)-; M 2 is as previously described; A represents an optionally substituted divalent non-aromatic hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R 4 is optionally substituted with (as defined above); or (iii)M 1 is -(CH2)-; M 2 is as previously described; A represents an optionally substituted divalent aromatic hydrocarbon ring group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and has 1 to 3 R 4 (R 4 is optionally substituted with (as defined above); or (2)1)g indicates 0; 2)(i)M 1 may be substituted C 2-4 represents an alkylene group; M 2 is as previously described; and, Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R 4 may be substituted with (as defined above); (ii) M 1 is -(CH2)-; M 2 is as previously described; and, Q is C 1-6 alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and has 1 to 3 R 4 (R 4 is optionally substituted with (as defined above); or (iii)M 1 is -(CH2)-; M 2 is as previously described; and Q represents an aromatic hydrocarbon ring group, and the group may be the same or different and may be composed of 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and Rb3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or -COR e (R e may be substituted C 1-6 and R a1 ~R a6 , and R b1 ~R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8 an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or -COR f (R f is C 1-6 alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group; R c1 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 alkyl group), or an optionally substituted aryl group; The compound A-1 or A-2, or a pharmaceutically acceptable salt thereof,

[0095] [Compound A-4] In formula (I), R 1 and R 2 taken together with the nitrogen atom to which they are attached, form the following formula (IIa):

[0096] [ka]

[0097] (wherein Rx is C optionally substituted with a hydroxyl group) 1-6 alkyl group, where two Rx together with the carbon atom to which they are attached form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; n1 represents an integer of 0 to 3. (wherein n1 is preferably an integer of 0 to 2, more preferably 0) forming a group represented by Any of the above [Compound A-1] to [Compound A-3] or a pharmaceutically acceptable salt thereof.

[0098] [Compound A-5] In formula (I), (1) g indicates 1, (2)(i)M 1 may be substituted C 2-4 represents an alkylene group, (ii) M 1 is -(CH2)-, and A represents an optionally substituted divalent non-aromatic hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; or (iii)M 1 is -(CH2)-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, optionally substituted aromatic heterocyclic group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (Rc3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group), or -COR e (R e may be substituted C 1-6 It represents an alkyl group. It may be substituted with an alkyl group; R a2 ~R a3 , and R b2 ~R b3 each independently represents a hydrogen atom, an optionally substituted cycloalkyl group, an optionally substituted heterocycloalkyl group, or -COR f (R f represents an optionally substituted hydrocarbon ring group; and R c2 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 represents an alkyl group or an optionally substituted aryl group; The above [Compound A-1] to [Compound A-4] or a pharmaceutically acceptable salt thereof.

[0099] [Compound A-6] In formula (I), g is 1; fR 3 are each independently -OR c1 (R c1 as described below); f represents an integer of 0 to 3; R 3a is a hydrogen atom or C 1-6 represents an alkyl group; A is C 3-8 Cycloalkylene group, C 3-8 Cycloalkenylene group, C 6-14 an arylene group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; Q is C 3-8 Cycloalkyl group or C 6-14 aryl groups, each of which may be the same or different and which is 1 to 3 R 4 (where R 4 are each independently 1-6 Alkoxy group, C 6-14 Aryl-C 1-6 C optionally substituted with an alkoxy group, a hydroxyl group, or a halogen atom 1-6 Alkyl group; Nitro group; -NR a2 R b2 (R a2 and R b2 as described below);-OR c2 (R c2 (as described below);-CO2R c3 (R c3 (See below);-CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group); a cyano group; or a halogen atom); M 1 is -(CH2) i - (wherein i represents 1 to 4); M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO- or -(CH2) j4 -CO-(CH2) j5 -(In the formula, R a4 ~R a5 is as described below, and j1 to j5 each independently represent an integer of 0 to 4; R a2 ~R a5 , and R b2 ~R b3are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 Alkyl group, C 2-8 Alkynyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group); R c1 ~R c3 are each independently a hydrogen atom, C 1-6 Alkyl group or -COR h (R h is C 1-6 alkyl group), The above-mentioned [Compound A-5] or [Compound A-6], or a pharmaceutically acceptable salt thereof.

[0100] [Compound A-7] R 1 and R 2 taken together with the nitrogen atom to which they are attached, form the following formula (IIa):

[0101] [ka]

[0102] (wherein n1 represents 0) forming a group represented by The compound described in the above [Compound A-6] or a pharmaceutically acceptable salt thereof.

[0103] [Compound A-8] (1) g indicates 0; (2)(i)M 1 may be substituted C 2-4 Indicates an alkylene group; (ii) M 1 is -(CH2)-, and Q is C 1-6alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 is optionally substituted with (as described in [1] above); or (iii)M 1 is -(CH2)-, Q represents an aromatic hydrocarbon ring group, and the group is the same or different and is composed of 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or -COR e (R e may be substituted C 1-6 It may be substituted with an alkyl group; R a2 ~R a3 , and R b2 ~R b3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group, optionally substituted C 2-8 an alkynyl group, an optionally substituted cycloalkyl group, an optionally substituted heterocycloalkyl group, or -COR f (R f is C 1-6an alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group), and R c2 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 Alkyl group, -COR h (R h is C 1-6 an alkyl group, or an optionally substituted aryl group; The above-mentioned [Compound A-5] or [Compound A-6], or a pharmaceutically acceptable salt thereof.

[0104] [Compound A-9] g is 0; fR 3 But, -OR c1 (R c1 is as described below); f is an integer from 0 to 3; Q is C 1-6 Alkyl group, C 3-14 Cycloalkyl groups, C 6-14 an aryl group or a 5- to 14-membered spirocyclic group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 are each independently C 1-6 Alkyl group, -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group), or -COR e (R e is C 1-6 optionally substituted with alkyl groups); M 1 But C 1-6C optionally substituted with alkyl group 1-4 represents an alkylene group; M 2 But -(CH2) j1 -or-(CH2) j2 -O-(CH2) j3 - (wherein j1 to j3 each independently represent an integer of 0 to 4); R a3 , and R b3 are each independently a hydrogen atom or C 3-8 represents a cycloalkyl group, and R c1 ~R c3 are each independently a hydrogen atom or C 1-6 The above-mentioned [Compound A-5] or [Compound A-6], or a pharmaceutically acceptable salt thereof, which is an alkyl group.

[0105] [Compound A-10] R 1 and R 2 taken together with the nitrogen atom to which they are attached, form the following formula (IIa):

[0106] [ka]

[0107] (wherein n1 represents 0) forming a group represented by The compound described in the above [Compound A-9] or a pharmaceutically acceptable salt thereof.

[0108] [Compound A-11] g is 1; fR 3 But, -OR c1 (R c1 is a hydrogen atom or -COR h (R h is C 1-6 alkyl group); f is 0 or 1; R 3a is a hydrogen atom or C1-6 is an alkyl group; A is C 3-8 is a cycloalkylene group; Q is C 6-14 aryl groups, each of which may be the same or different and may have 1 to 3 R 4 (where R 4 are each independently C 1-6 Alkoxy group, C 6-14 Aryl-C 1-6 C optionally substituted with an alkoxy group, a hydroxyl group, or a halogen atom 1-6 alkyl groups; -NR a2 R b2 (R a2 and R b2 are each independently a hydrogen atom, C 1-6 Alkyl group, or -COR f (R f is C 1-6 Alkyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl groups); -CO2R c3 (R c3 is C 1-6 alkyl group); -CONR a3 R b3 (R a3 and R b3 are each independently a hydrogen atom, C 1-6 C optionally substituted with an alkoxy group 1-6 Alkyl group, C 2-8 Alkynyl group, C 3-8 hydrocarbon ring group, or C 3-8 heterocycloalkyl group, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterocyclic bridged group; or (indicating halogen atoms) may be substituted with; M 1 is -(CH2)i - (wherein i is 1 to 4); M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 - (wherein j1 to j3 each independently represent an integer of 0 to 4). The compound described in the above [Compound A-7] or a pharmaceutically acceptable salt thereof.

[0109] [Compound A-11] g is 0; fR 3 is a hydroxyl group; f is an integer of 0 or 1; R 3a is a hydrogen atom; Q is C 3-14 Cycloalkyl groups, C 6-14 an aryl group or a 5- to 14-membered spirocyclic group; M 1 But C 1-6 C optionally substituted with alkyl group 1-4 is an alkylene group; M 2 But -(CH2) j1 - (wherein j1 represents 0) The compound described in the above [Compound A-10] or a pharmaceutically acceptable salt thereof.

[0110] [Compound A-12] The compound represented by formula (I) is one or more compounds selected from the group of compounds represented by the following structural formulas: The compound according to any one of the above [Compound A-1] to [Compound A-11] or a pharmaceutically acceptable salt thereof.

[0111] [ka]

[0112] [ka]

[0113] [ka]

[0114] [ka]

[0115] [ka]

[0116] [ka]

[0117] [ka]

[0118] [ka]

[0119] In this embodiment, compound (I) can be used in either the free form or the form of a pharmaceutically acceptable salt thereof. Those skilled in the art can carry out the present invention by appropriately selecting either form based on the properties of each compound (I) used. Pharmaceutically acceptable salts include salts with inorganic acids such as hydrochloride, hydrobromide, sulfate, phosphate, etc.; salts with organic acids such as acetate, fumarate, oxalate, citrate, methanesulfonate, benzenesulfonate, tosylate, maleate, etc.; salts with bases such as alkali metal salts such as sodium salt, potassium salt, etc., alkaline earth metal salts such as calcium salt, etc.; salts with amino acids such as glycine salt, lysine salt, arginine salt, ornithine salt, glutamate, aspartate, etc.

[0120] Preferred specific examples of the compound (I) represented by the formula (I) are as described above, but other preferred specific examples include the following compounds.

[0121] [Compound B-1] In formula (I), R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form the following formulae (IIa) to (IIe):

[0122] [ka]

[0123] (In the formula, Rx and Ry each independently represent an oxo group, an optionally substituted aryloxy group, or an optionally substituted C 1-6 represents an alkyl group, wherein two Rx and two Ry may each independently be joined together with the carbon atom to which they are attached to form a heterocycloalkane or a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 represents an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R 1 and R 2 each independently represents an optionally substituted C 1-6represents an alkyl group; fR 3 are each independently -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R 3a indicates a hydrogen atom; A represents an optionally substituted divalent hydrocarbon ring group or an optionally substituted heterocycloalkylene group; g indicates 0 or 1; Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, optionally substituted aromatic heterocyclic group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group), or -COR e (R e may be substituted C 1-6 It may be substituted with an alkyl group; M 1 is -(CH2) i - (wherein i represents 1 to 4); M2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO-, -(CH2) j4 -CO-(CH2) j5 -, -(CH2) j6 -CH(OH)-(CH2) j7 -, or -NR a6 - (In the formula, R a4 ~R a6 is as described below, and j1 to j7 each independently represent an integer of 0 to 4; R a1 ~R a6 , and R b1 ~R b3 each independently represents a hydrogen atom, an optionally substituted cycloalkyl group, an optionally substituted heterocycloalkyl group, or -COR f (R f represents an optionally substituted hydrocarbon ring group; R c1 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 It represents an alkyl group or an optionally substituted aryl group. however, (1) M 1 is -(CH2)-, g is 0, and M 2 -(CH2) j1 - when j1 is 0 and Q is benzene R 4 is not a pyrazolyl group substituted with a methyl group. (2) M 1 is -(CH2)-, g is 1, A is benzene, and M 2 But -(CH2) j1 - when j1 is 0 and Q is pyrazole R 4 is not a methyl group; or a pharmaceutically acceptable salt thereof.

[0124] [Compound B-2] R 1 and R 2 together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe):

[0125] [ka]

[0126] wherein Rx and Ry each independently represent an oxo group, an optionally substituted C 6-14 an aryloxy group or an optionally substituted C 1-6 alkyl group, wherein two Rx and two Ry are each independently joined together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R 1 and R 2 each independently represents an optionally substituted C 1-6 is an alkyl group; A is an optionally substituted divalent C 3-14 a hydrocarbon ring group or an optionally substituted 3- to 8-membered heterocycloalkylene group; Q is C 1-6 Alkyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, optionally substituted 5- to 8-membered aromatic heterocyclic group, nitro group, -NR a2 R b2 (Ra2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group), or -COR e (R e may be substituted C 1-6 It may be substituted with an alkyl group; R a1 ~R a6 , and R b1 ~R b3 are each independently a hydrogen atom, an optionally substituted C 3-14 Cycloalkyl groups (preferably C 3-8 cycloalkyl group), an optionally substituted 3- to 8-membered heterocycloalkyl group, or -COR f (R f may be substituted C 3-8 hydrocarbon ring group); R c1 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 alkyl group or optionally substituted C 6-14 is an aryl group, The compound described in the above [Compound B-1] or a pharmaceutically acceptable salt thereof.

[0127] [Compound B-3] R 1 and R 2 together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe):

[0128] [ka]

[0129] (Wherein Rx and Ry each independently represent an oxo group, C 6-14 C optionally substituted with an aryloxy group or a hydroxyl group 1-6 alkyl group, wherein two Rx and two Ry are each independently joined together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C 3-8 Rz may form a hydrogen atom or C 1-6 is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R 1 and R 2 are each independently 1-6 C optionally substituted with an alkoxy group 1-6 is an alkyl group; A is a divalent C optionally substituted with a hydroxyl group 3-14 a hydrocarbon ring group or a 3- to 8-membered heterocycloalkylene group; Q is C 1-6 Alkyl group, C 3-14 a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R 4 (where R 4 C each independently optionally substituted with a group selected from a hydroxyl group and a halogen atom 1-6 Alkyl group, C 1-6 5- to 8-membered aromatic heterocyclic group optionally substituted with an alkyl group, a nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3(R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group), or -COR e (R e is C 1-6 (Alkyl group) may be substituted with; R a1 ~R a6 , and R b1 ~R b3 are each independently a hydrogen atom, C 3-14 a cycloalkyl group, a 3- to 8-membered heterocycloalkyl group, or -COR f (R f is C 3-8 a hydrocarbon ring group); R c1 ~R c3 are each independently a hydrogen atom, C 1-6 Alkyl group, or C 6-14 is an aryl group, The compound according to the above [Compound B-1] or [Compound B-2] or a pharmaceutically acceptable salt thereof.

[0130] [Compound B-4] (1)1)g indicates 1; 2)(i)M 1 But -(CH2) i - (wherein i is 2 to 4); (ii) M 1 is -(CH2)-, and A represents an optionally substituted divalent non-aromatic hydrocarbon ring group or an optionally substituted heterocycloalkylene group; or (iii)M 1 is -(CH2)-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q is C 1-6represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 may be substituted with (as described above in [Compound B-1]); or (2)1) g indicates 0; 2)(i)M 1 But -(CH2) i - (wherein i is 2 to 4); (ii) M 1 is -(CH2)-, and Q is C 1-6 alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 may be substituted with (as described above in [Compound B-1]); or (iii)M 1 is -(CH2)-, Q may be the same or different and may be 1 to 3 R 4 represents an aromatic hydrocarbon ring group optionally substituted by 4 each independently represents an optionally substituted C 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group), or -COR e (R e may be substituted C1-6 alkyl group), R a2 ~R a3 , and R b2 ~R b3 each independently represents a hydrogen atom, an optionally substituted cycloalkyl group, an optionally substituted heterocycloalkyl group, or -COR f (R f represents an optionally substituted hydrocarbon ring group), and R c2 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 represents an alkyl group or an optionally substituted aryl group, The compound described in the above [Compound B-1] or a pharmaceutically acceptable salt thereof.

[0131] The compound described above in [Compound B-4] or a pharmaceutically acceptable salt thereof corresponds to the compound described below in [Compound B-4A] or a pharmaceutically acceptable salt thereof.

[0132] [Compound B-4A] In formula (I), R 1 and R 2 are taken together with the nitrogen atom to which they are attached to form the following formulae (IIa) to (IIe):

[0133] [ka]

[0134] (In the formula, Rx and Ry each independently represent an oxo group, an optionally substituted aryloxy group, or an optionally substituted C 1-6 represents an alkyl group, wherein two Rx and two Ry may each independently be joined together with the carbon atom to which they are attached to form a heterocycloalkane or a cycloalkane; Rz is a hydrogen atom or an optionally substituted C 1-6 represents an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R 1 and R 2 each independently represents an optionally substituted C 1-6 represents an alkyl group; fR 3 are each independently -NR a1 R b1 (R a1 and R b1 (See below), -OR c1 (R c1 indicates a halogen atom; f represents an integer of 0 to 3; R 3a indicates a hydrogen atom; (1)1)g indicates 1, 2)(i)M 1 is -(CH2) i - (wherein i is 2 to 4); M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO-, -(CH2) j4 -CO-(CH2) j5 -, -(CH2) j6 -CH(OH)-(CH2) j7 -, or -NR a6 - (In the formula, R a4 ~R a6 is as described below, and j1 to j7 each independently represent an integer of 0 to 4; A represents an optionally substituted divalent hydrocarbon ring group or an optionally substituted heterocycloalkylene group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R4 each independently represents an optionally substituted C 1-6 Alkyl group, optionally substituted aromatic heterocyclic group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group), or -COR e (R e may be substituted C 1-6 alkyl group); (ii) M 1 is -(CH2)-; M 2 is as previously described; A represents an optionally substituted divalent non-aromatic hydrocarbon ring group or an optionally substituted heterocycloalkylene group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R 4 is optionally substituted with (as defined above); or (iii)M 1 is -(CH2)-; M 2 is as previously described; A represents an optionally substituted divalent aromatic hydrocarbon ring group; and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and has 1 to 3 R4 (R 4 is optionally substituted with (as defined above); or (2)1)g indicates 0; 2)(i)M 1 is -(CH2) i - (wherein i is 2 to 4); M 2 is as previously described; and, Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group may be the same or different and may have 1 to 3 R 4 (R 4 may be substituted with (as defined above); (ii) M 1 is -(CH2)-; M 2 is as previously described; and, Q is C 1-6 alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and has 1 to 3 R 4 (R 4 is optionally substituted with (as defined above); or (iii)M 1 is -(CH2)-; M 2 is as previously described; and Q represents an aromatic hydrocarbon ring group, and may be the same or different and may be 1 to 3 R 4 (where R 4 each independently represents an optionally substituted C 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONRa3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group), or -COR e (R e may be substituted C 1-6 and R a1 ~R a6 , and R b1 ~R b3 each independently represents a hydrogen atom, an optionally substituted cycloalkyl group, an optionally substituted heterocycloalkyl group, or -COR f (R f represents an optionally substituted hydrocarbon ring group; R c1 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 represents an alkyl group or an optionally substituted aryl group; or a pharmaceutically acceptable salt thereof.

[0135] [Compound B-5] R 1 and R 2 taken together with the nitrogen atom to which they are attached, form the following formula (IIa):

[0136] [ka]

[0137] (wherein Rx is C optionally substituted with a hydroxyl group) 1-6 alkyl group, where two Rx together with the carbon atom to which they are attached form a 3- to 8-membered heterocycloalkane or C 3-8 may form a cycloalkane; n1 represents an integer between 0 and 3) forming a group represented by The compound or a pharmaceutically acceptable salt thereof according to any one of the above [Compound B-1], [Compound B-2], [Compound B-3], [Compound B-4], and [Compound B-4A].

[0138] [Compound B-6] (1) g indicates 1; (2)(i)M 1 But -(CH2) i - (wherein i is 2 to 4); (ii) M 1 is -(CH2)-, and A represents an optionally substituted divalent non-aromatic hydrocarbon ring group or an optionally substituted heterocycloalkylene group; or (iii)M 1 is -(CH2)-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q is C 1-6 represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 may be substituted with (as described above in [Compound B-1]); The compound or a pharmaceutically acceptable salt thereof according to any one of the above [Compound B-1], [Compound B-4], [Compound B-4A] and [Compound B-5].

[0139] [Compound B-7] g is 1; fR 3 are each independently -OR c1 (R c1 as described below); f represents an integer of 0 to 3; A is C 3-8 Cycloalkylene group, C 3-8 Cycloalkenylene group, C 6-14 an arylene group or a 3- to 8-membered heterocycloalkylene group; Q is C3-8 Cycloalkyl group or C 6-14 aryl groups, each of which may be the same or different and which is 1 to 3 R 4 (where R 4 each independently represents a C optionally substituted with a halogen atom; 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be substituted with a 3- to 8-membered heterocycloalkyl group together with the nitrogen atom to which they are attached), a cyano group, or a halogen atom; M 1 is -(CH2) i - (wherein i represents 1 to 4); M 2 is -(CH2) j1 -, -(CH2) j2 -O-(CH2) j3 -,-CONR a4 -, -NR a5 CO- or -(CH2) j4 -CO-(CH2) j5 -(In the formula, R a4 ~R a5 is as described below, and j1 to j5 each independently represent an integer of 0 to 4; R a2 ~R a5 , and R b2 ~R b3 are each independently a hydrogen atom; R c1 ~R c2 are each independently a hydrogen atom or C 1-6 is an alkyl group, A compound or a pharmaceutically acceptable salt thereof according to any one of the above [Compound B-1], [Compound B-2], [Compound B-3], [Compound B-4], [Compound B-4A], [Compound B-5], and [Compound B-6].

[0140] [Compound B-8] (1) g indicates 0; (2)(i)M 1 But -(CH2) i - (wherein i is 2 to 4); (ii) M 1 is -(CH2)-, and Q is C 1-6 alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and has 1 to 3 R 4 (where R 4 may be substituted with (as described above in [Compound B-1]); or (iii)M 1 is -(CH2)-, Q may be the same or different and may be 1 to 3 R 4 represents an aromatic hydrocarbon ring group optionally substituted by 4 each independently represents an optionally substituted C 1-6 Alkyl group, nitro group, -NR a2 R b2 (R a2 and R b2 (See below), -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (as described below), -CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3 may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group), or -COR e (Re may be substituted C 1-6 alkyl group), R a2 ~R a3 , and R b2 ~R b3 each independently represents a hydrogen atom, an optionally substituted cycloalkyl group, an optionally substituted heterocycloalkyl group, or -COR f (R f represents an optionally substituted hydrocarbon ring group), and R c2 ~R c3 are each independently a hydrogen atom, an optionally substituted C 1-6 represents an alkyl group or an optionally substituted aryl group; The compound or a pharmaceutically acceptable salt thereof according to any one of the above [Compound B-1], [Compound B-4], [Compound B-4A], and [Compound B-5].

[0141] [Compound B-9] g is 0; fR 3 But, -OR c1 (R c1 is as described below); f is an integer from 0 to 3; Q is C 1-6 Alkyl group, C 3-8 Cycloalkyl group, or C 6-14 aryl groups, each of which may be the same or different and which is 1 to 3 R 4 (where R 4 are each independently C 1-6 Alkyl group, -OR c2 (R c2 as described below), halogen atoms, cyano groups, -CO2R c3 (R c3 (See below)-CONR a3 R b3 (R a3 and R b3 is as follows, where R a3 and R b3may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group), or -COR e (R e is C 1-6 optionally substituted with alkyl groups); M 1 But -(CH2) i - (wherein i represents 1 to 4); M 2 But -(CH2) j1 -or-(CH2) j2 -O-(CH2) j3 - (wherein j1 to j3 each independently represent an integer of 0 to 4); R a3 , and R b3 are each independently a hydrogen atom or C 3-8 represents a cycloalkyl group, and R c1 ~R c3 are each independently a hydrogen atom or C 1-6 The compound or a pharmaceutically acceptable salt thereof according to any one of the above [Compound B-1], [Compound B-2], [Compound B-3], [Compound B-4], [Compound B-4A], [Compound B-5] or [Compound B-8], wherein the alkyl group is an alkyl group.

[0142] [Method for producing compound (I) or a pharmaceutically acceptable salt thereof] Representative embodiments of the method for producing Compound (I) or a pharmaceutically acceptable salt thereof are given below. However, the method for producing Compound (I) or a pharmaceutically acceptable salt thereof is not limited to these, and a person skilled in the art can produce Compound (I) or a pharmaceutically acceptable salt thereof by appropriately selecting and carrying out a synthesis scheme depending on the target compound.

[0143] (Manufacturing method 1)

[0144] [ka]

[0145] (In the formula, R 1 , R 2 , R 3 , R 3a , A, Q, M 1 , M 2 , f and g have the same meanings as in the compound represented by formula (I), and L represents a leaving group.

[0146] Compound (I) or a pharmaceutically acceptable salt thereof can be prepared by reacting compound (III) or a salt thereof with compound (IV) or a salt thereof. The leaving group represented by L is a halogen atom, a sulfonyloxy group (e.g., C 1-6 alkylsulfonyloxy groups (eg, methanesulfonyloxy groups), etc. Examples of salts of compounds (III) and (IV) include those exemplified for compound (I). The conditions for the substitution reaction are not particularly limited, and those skilled in the art can select the solvent, temperature, and other conditions appropriately depending on the raw material compounds to be subjected to the reaction. Any solvent that does not adversely affect the reaction can be used, and a suitable example of the solvent is N,N-dimethylformamide. The reaction can be carried out in the presence of a suitable base, such as sodium hydride, sodium tert-butoxide, or potassium carbonate. The reaction can be carried out within a temperature range, for example, at room temperature, warmed, or heated. The above is an overview of the substitution reaction, but for more details, please refer to the reaction conditions described in various examples in the section [Examples] below.

[0147] (Manufacturing method 2)

[0148] [ka]

[0149] (In the formula, R 1 , R 2 , R 3 , R 3a , A, Q, M 1 , M 2 , f and g have the same meanings as in the compound represented by formula (I),

[0150] Compound (I) or a pharmaceutically acceptable salt thereof can be prepared by reacting compound (V) or a salt thereof with compound (VI) or a salt thereof. Examples of salts of compounds (V) and (VI) include those exemplified for compound (I). The conditions for the condensation reaction are not particularly limited, and a person skilled in the art can appropriately select the solvent, temperature, and other conditions depending on the raw material compounds to be subjected to the reaction. Any solvent that does not adversely affect the reaction can be used, and a suitable example of the solvent is N,N-dimethylformamide. The reaction can be carried out in the presence of a suitable base, such as N,N-diisopropylethylamine. The reaction can be carried out in the presence of a suitable condensing agent, such as 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate. The reaction can be carried out within a temperature range, for example, at room temperature or at elevated temperatures. The above is an overview of the condensation reaction, but for more details, please refer to the reaction conditions described in various examples in the section [Examples] below.

[0151] Representative methods for producing Compound (I) or a pharmaceutically acceptable salt thereof have been described above. As the starting compounds used in each production method, known compounds or compounds obtained by starting from known compounds and using the methods described in the various Examples in the "Examples" section below can be used. For manufacturing methods other than the above-mentioned (Manufacturing Method 1) and (Manufacturing Method 2), reference can be made to the manufacturing methods described in the various examples in the section [Examples] below.

[0152] [Use of Compound (I) or its pharmaceutically acceptable salts and prodrugs] As demonstrated in the test examples described below, compound (I) has the effect of activating autophagy. Therefore, through this activating effect, compound (I) or a pharmaceutically acceptable salt thereof and a prodrug thereof described below (hereinafter also referred to as "compound (I) of the present application") normalize, maintain, and / or activate autophagy, and are useful for the prevention or treatment of diseases caused by decreased autophagy or diseases whose pathology is suppressed or ameliorated by increased autophagy.

[0153] (About the target diseases) Such diseases include neurodegenerative diseases (e.g., Alzheimer's disease, Parkinson's disease, Huntington's disease, amyotrophic lateral sclerosis, ischemic brain injury, focal cortical dysplasia, frontotemporal dementia, neuronal ceroid lipofuscinosis, dementia with Lewy bodies, spinocerebellar degeneration, cortical atrophy, epilepsy, childhood-onset, beta-propeller protein-associated neurodegeneration, spastic quadriplegia, primary microcephaly, Hereditary spastic paraplegia, ataxia with spasticity, Rett syndrome, Joubert syndrome, leukoencephalopathy, dystonia, Cednik syndrome, Pelizaeus-Merzbacher disease, West syndrome, sensory autonomic neuropathy type IF, sensory autonomic neuropathy type II, distal hereditary motor neuropathy, Charcot-Marie-Tooth disease, El-Hattab-Alkuraya syndrome, autosomal recessive spinocerebellar ataxia, cerebral palsy, etc.); Cardiovascular, musculoskeletal, or skeletal disease (e.g., cardiomyopathy, ischemia-reperfusion injury, atherosclerosis, Danon disease, distal myopathy, X-linked myopathy, X-linked myotubular myopathy, dilated cardiomyopathy, inclusion body myositis, exercise intolerance, muscular dystrophy, osteoarthritis, osteoporosis, Paget's disease of bone, sarcopenia, Kashin-Beck disease, etc.); Pulmonary disease (e.g., chronic obstructive pulmonary disease, pulmonary fibrosis, cystic fibrosis, sarcoidosis, etc.); kidney disease (e.g., acute kidney injury, diabetic nephropathy, polycystic kidney disease, chronic kidney disease, renal fibrosis, focal segmental glomerulosclerosis, renal failure, etc.); metabolic syndrome (e.g., diabetes, nonalcoholic fatty liver disease, liver fibrosis, fatty liver, metabolic syndrome, obesity, etc.); liver pathology (e.g., cirrhosis, acute liver failure, hereditary liver disorders, α1-antitrypsin deficiency, hyperammonemia, cholestasis, etc.); Immune, inflammatory, and immune-related diseases (e.g., bacterial infections, fungal infections, viral infections, inflammatory bowel disease, ulcerative colitis, autoimmune diseases, psoriasis, atopic dermatitis, vitiligo, systemic lupus erythematosus, multiple sclerosis, Crohn's disease, asthma, tuberculosis, leprosy, Behçet's disease, etc.); Eye diseases (e.g., autosomal dominant optic atrophy, age-related macular degeneration, cataracts, glaucoma, primary open-angle glaucoma, gaze palsy, Vogt-Koyanagi-Harada syndrome, etc.); Reproductive system dysfunction (e.g., male infertility); Congenital multisystem disorders (e.g., Vici syndrome, Zellweger syndrome, congenital glycosylation disorders, Zimmerman-Laband syndrome, Hermansky-Pudlak syndrome, multisystem proteinopathy, hereditary spastic paraplegia, etc.); Cancer (e.g., bladder cancer, bone cancer, breast cancer, colorectal cancer, liver tumor, intestinal cancer, lung cancer, black cancer, pancreatic cancer, prostate cancer, kidney cancer, etc.); Examples include:

[0154] (Regarding the mode of use) When compound (I) of the present application is used as a pharmaceutical for the prevention or treatment of diseases caused by decreased autophagy function or diseases whose pathology is suppressed or improved by enhanced autophagy function, compound (I) of the present application can be used alone or in the form of a pharmaceutical composition containing compound (I) of the present application as an active ingredient together with a pharmaceutically acceptable carrier.

[0155] As used herein, "prevention" includes preventing the onset of a disease (including symptoms of the disease) (either the entire pathology or one or more pathologies) and delaying the onset of the disease. A "prophylactically effective amount" refers to a dose of Compound (I) of the present application sufficient to achieve such a purpose. As used herein, "treatment" includes curing a disease (including symptoms of the disease) (the entire pathology or one or more pathologies), ameliorating the disease, and inhibiting the progression of the severity of the disease. A "therapeutically effective amount" refers to a dose of Compound (I) of the present application sufficient to achieve such a purpose.

[0156] Examples of such pharmaceutical compositions include tablets (including sugar-coated tablets, film-coated tablets, sublingual tablets, orally disintegrating tablets, buccal tablets, etc.), pills, powders, granules, capsules (including soft capsules and microcapsules), syrups, liquids, emulsions, suspensions, controlled-release preparations (e.g., immediate-release preparations, sustained-release preparations, sustained-release microcapsules), aerosols, films (e.g., orally disintegrating films, oral mucosal patch films), injections (e.g., subcutaneous injections, intravenous injections (e.g., bolus), intramuscular injections, intraperitoneal injections), drip infusions, transdermal preparations, ointments, lotions, patches, suppositories (e.g., rectal suppositories, vaginal suppositories), pellets, nasal preparations, pulmonary preparations (inhalants), and eye drops.

[0157] As used herein, the term "pharmaceutically acceptable carrier" refers to any of a variety of carriers commonly used in the field of pharmaceutical formulation technology.

[0158] Specific examples of "pharmaceutically acceptable carriers" that can be used in solid preparations include excipients (e.g., lactose, sucrose, D-mannitol, starch, corn starch, crystalline cellulose, light anhydrous silicic acid, etc.), lubricants (e.g., magnesium stearate, talc, colloidal silica, etc.), binders (e.g., crystalline cellulose, sucrose, D-mannitol, dextrin, hydroxypropyl cellulose, hydroxypropylmethylcellulose, polyvinylpyrrolidone, starch, sucrose, gelatin, methylcellulose, sodium carboxymethylcellulose, etc.), and disintegrants (e.g., starch, carboxymethylcellulose, calcium carboxymethylcellulose, sodium carboxymethylstarch, L-hydroxypropylcellulose, etc.).

[0159] Liquid preparations may contain solvents (e.g., water for injection, isotonic saline, alcohol, propylene glycol, macrogol, sesame oil, etc.), solubilizing agents (e.g., polyethylene glycol, propylene glycol, D-mannitol, benzyl benzoate, ethanol, triethanolamine, sodium carbonate, sodium citrate, etc.), suspending agents (e.g., surfactants such as stearyltriethanolamine, sodium lauryl sulfate, laurylaminopropionic acid, lecithin, benzalkonium chloride, glycerin monostearate, etc.; hydrophilic polymers such as polyvinyl alcohol, polyvinylpyrrolidone, sodium carboxymethylcellulose, methylcellulose, hydroxymethylcellulose, hydroxypropylcellulose, etc.), isotonic agents (e.g., glucose, D-sorbitol, sodium chloride, glycerin, D-mannitol, etc.), buffers (e.g., buffer solutions such as phosphates and citrates), and soothing agents (e.g., benzyl alcohol, etc.).

[0160] If necessary, formulation additives such as preservatives (e.g., parahydroxybenzoic acid esters, chlorobutanol, benzyl alcohol, sorbic acid, etc.), antioxidants (e.g., sulfites, ascorbic acid, α-tocopherol, etc.), colorants, sweeteners, etc. may be further added.

[0161] The above pharmaceutical compositions can be prepared by adding the compound of the present invention in an amount of usually 0.01 to 99% (w / w), preferably 0.1 to 85% (w / w), based on the total amount of the formulation, although this varies depending on the dosage form, administration method, carrier, etc. The pharmaceutical compositions can be prepared by conventional methods in the field of formulation technology depending on the form. The pharmaceutical compositions may be formed into sustained-release preparations containing the active ingredient.

[0162] (Regarding administration subjects) The compound (I) of the present invention is expected to have low toxicity and few side effects, and has excellent properties as a pharmaceutical. Therefore, the compound (I) of the present invention can be safely administered to mammals (e.g., humans, dogs, or cats, particularly humans).

[0163] (Regarding administration route) The compound (I) of the present application may be administered alone or as a pharmaceutical composition orally or parenterally (e.g., intravenously, intramuscularly, subcutaneously, intraorganically, intranasally, intradermally, by ophthalmic administration, intracerebrally, intrarectally, intravaginally, intraperitoneally, and into a lesion).

[0164] (Dosage) The dose of Compound (I) of the present invention varies depending on the subject, route of administration, and age and symptoms of the subject, but is not particularly limited. For example, the dose of Compound (I) is 1 to 250 mg per oral administration, and 0.1 to 1000 mg per parenteral administration.

[0165] (Use as a prodrug) Compound (I) can be used in the form of a prodrug. Use of such a prodrug is also encompassed within the scope of the present invention. A prodrug of compound (I) refers to a compound that is converted to compound (I) by a reaction with an enzyme, gastric acid, or the like under physiological conditions in a living body, i.e., a compound that is converted to compound (I) by enzymatic oxidation, reduction, hydrolysis, or the like, or a compound that is converted to compound (I) by hydrolysis, etc., with gastric acid, or the like. Prodrugs of compound (I) include compounds in which the amino group of compound (I) is acylated, alkylated, or phosphorylated [for example, compounds in which the amino group of compound (I) is eicosanoylated, alanylated, pentylaminocarbonylated, (5-methyl-2-oxo-1,3-dioxolen-4-yl)methoxycarbonylated, tetrahydrofuranylated, pyrrolidylmethylated, pivaloyloxymethylated, or tert-butylated, etc.]; compounds in which the hydroxyl group of compound (I) is acylated, alkylated, phosphorylated, or borated [for example, compounds in which the hydroxyl group of compound (I) is acetylated, palmitoylated, propanoylated, pivaloylated, succinylated, etc.]; compounds in which the carboxyl group of compound (I) is esterified or amidated (e.g., compounds in which the carboxyl group of compound (I) is ethyl esterified, phenyl esterified, carboxymethyl esterified, dimethylaminomethyl esterified, pivaloyloxymethyl esterified, ethoxycarbonyloxyethyl esterified, phthalidyl esterified, (5-methyl-2-oxo-1,3-dioxolen-4-yl)methyl esterified, cyclohexyloxycarbonylethyl esterified, methylamidized, etc.). These compounds can be produced from compound (I) by methods known per se. Furthermore, the prodrug of compound (I) may be one that is converted into compound (I) under physiological conditions, as described in "Drug Development," Hirokawa Publishing, 1990, Vol. 7, Molecular Design, pp. 163 to 198. The prodrug of compound (I) may be in the form of a salt. Suitable salts include the pharmaceutically acceptable salts exemplified for compound (I).

[0166] Compound (I) may be any of a hydrate, a non-hydrate, a solvate, and a non-solvate. Compound (I) may also contain isotopes (e.g., 2 H, 3 H, 11 C. 14 C. 18 F, 35 S, 125 The compound may be a compound labeled or substituted with an isotope, such as I, and a compound labeled or substituted with an isotope can be used, for example, as a tracer used in positron emission tomography (PET) (PET tracer), and may be useful in fields such as medical diagnosis. 1 H 2 Deuterium-converted compounds converted to H(D) are also encompassed by Compound (I). Compound (I) also encompasses tautomers. Compound (I) may be a pharmaceutically acceptable cocrystal or cocrystal salt. Here, a cocrystal or cocrystal salt refers to a crystalline substance composed of two or more distinct solids at room temperature, each of which has different physical properties (e.g., structure, melting point, heat of fusion, hygroscopicity, solubility, stability, etc.). A cocrystal or cocrystal salt can be prepared by a known cocrystallization method.

[0167] (Concomitant use with other drugs) The compound (I) of the present invention may be used in combination with other active ingredients (hereinafter abbreviated as concomitant drugs). As the concomitant drug, a compound or a salt thereof that can have a preventive and / or therapeutic effect can be appropriately combined depending on the disease to be prevented or treated. By combining the compound (I) of the present application with a concomitant drug, (1) The dose of the compound (I) of the present application or a concomitant drug can be reduced compared to when the compound (I) or a concomitant drug is administered alone. (2) Drugs to be used in combination with Compound (I) of the present invention can be selected depending on the patient's symptoms (mild, severe, etc.). (3) By selecting a concomitant drug having a different mechanism of action from that of the compound (I) of the present invention, the treatment period can be extended. (4) By selecting a concomitant drug having a different mechanism of action from that of the compound (I) of the present application, the therapeutic effect can be sustained. (5) By using the compound (I) of the present invention in combination with a concomitant drug, excellent effects such as a synergistic effect can be obtained.

[0168] Hereinafter, the combined use of the compound (I) of the present invention and a concomitant drug will be referred to as the "concomitant drug of the present invention." When using the present combination drug, the administration timing of the compound (I) of the present application and the concomitant drug is not limited, and the compound (I) of the present application or a pharmaceutical composition thereof and the concomitant drug or a pharmaceutical composition thereof may be administered to the subject simultaneously or at staggered times. The dose of the concomitant drug may be in accordance with the dose used clinically and may be appropriately selected depending on the subject, administration route, disease, combination, etc. The administration form of the present combination drug is not particularly limited, as long as the compound (I) of the present application and the concomitant drug are combined at the time of administration. Examples of such administration forms include (1) administration of a single preparation obtained by simultaneously formulating the compound (I) of the present application and the concomitant drug, (2) simultaneous administration of two preparations obtained by separately formulating the compound (I) of the present application and the concomitant drug via the same administration route, (3) administration of two preparations obtained by separately formulating the compound (I) of the present application and the concomitant drug via the same administration route at different times, (4) simultaneous administration of two preparations obtained by separately formulating the compound (I) of the present application and the concomitant drug via different administration routes, and (5) administration of two preparations obtained by separately formulating the compound (I) of the present application and the concomitant drug via different administration routes at different times (e.g., administration of the compound (I) of the present application followed by the concomitant drug, or administration in the reverse order). The mixing ratio of the compound (I) of the present invention to the concomitant drug in the present combination agent can be appropriately selected depending on the subject of administration, the administration route, the disease, etc. For example, the content of the compound (I) of the present application in the present combination drug varies depending on the form of the formulation, but is usually about 0.01 to 100% by weight, preferably about 0.1 to 50% by weight, and more preferably about 0.5 to 20% by weight based on the total weight of the formulation. The content of the concomitant drug in the present combination agent varies depending on the form of the preparation, but is usually about 0.01 to 100% by weight, preferably about 0.1 to 50% by weight, and more preferably about 0.5 to 20% by weight of the total preparation. The content of additives such as carriers in the present combination drug varies depending on the form of the formulation, but is usually about 1 to 99.99% by weight, preferably about 10 to 90% by weight, based on the total weight of the formulation. Furthermore, when the compound (I) of the present invention and the concomitant drug are formulated separately, the contents may be similar. [Example]

[0169] The present invention will be specifically described below based on examples, test examples, and formulation examples, but the present invention is not limited to these examples. Those skilled in the art can modify the embodiments of the present invention in various aspects without departing from the spirit of the present invention, and such modifications are also included in the scope of the present invention.

[0170] [Example: Preparation of Compound (I) or a Pharmaceutically Acceptable Salt thereof] Example 1 Morpholino(1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.2 g of 4-azaindole-3-carboxylic acid in 3 mL of dichloromethane, 0.127 mL of oxalyl chloride and 1 drop of N,N-dimethylformamide were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at 0°C for 1 hour. Subsequently, 0.43 g of morpholine and 0.41 mL of triethylamine were added at 0°C, and the mixture was stirred at room temperature for 1 hour. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:15:2), and the solvent was evaporated under reduced pressure to obtain 0.053 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. (2) To a solution of 0.053 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.011 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.054 g of 4-phenylbutyl bromide and 0.019 g of potassium iodide were then added, and the mixture was stirred at room temperature for 19 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.022 g of morpholino(1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.51 (m, 1H), 7.81 (s, 1H), 7.62-7.60 (m,1H), 7.29-7.26 (m, 2H), 7.21-7.12 (m, 4H), 4.12 (t, J = 7.2 Hz, 2H), 3.80 (s, 8H), 2.65 (t, J = 7.6 Hz, 2H), 1.94-1.87 (m, 2H), 1.72-1.64 (m, 2H)

[0171] Example 2 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid methyl ester (1) To 1.50 g of 3-butyn-1-ol, 0.122 g of copper(I) iodide, and 0.124 g of tetrakis(triphenylphosphine)palladium(0), 1.5 mL of triethylamine and 5.31 g of 3-(methoxycarbonyl)-1-iodobenzene were added under a nitrogen atmosphere at room temperature and stirred at 50°C for 24 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 3.60 g of methyl 3-(4-hydroxybut-1-yn-1-yl)benzoate. (2) To a solution of 3.60 g of methyl 3-(4-hydroxybut-1-yn-1-yl)benzoate in 30 mL of dichloromethane, 6.43 g of carbon tetrabromide and 5.09 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 26 hours. The solvent was then distilled off under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then distilled off under reduced pressure to obtain 3.56 g of methyl 3-(4-bromobut-1-yn-1-yl)benzoate. (3) 2.27 g of palladium-fibroin was added to 3.60 g of methyl 3-(4-bromobut-1-yn-1-yl)benzoate under a nitrogen atmosphere, followed by the addition of 40 mL of methanol and stirring at room temperature for 24 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to obtain 3.31 g of methyl 3-(4-bromobutyl)benzoate. (4) To a solution of 0.030 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.008 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. Further, 0.070 g of methyl 3-(4-bromobutyl)benzoate and 0.011 g of potassium iodide were added, and the mixture was stirred at room temperature for 72 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and then the solvent was distilled off under reduced pressure to obtain 0.023 g of methyl 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoate. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.51 (m, 1H), 7.88-7.86 (m, 1H), 7.83-7.80 (m, 2H), 7.62-7.60 (m, 1H), 7.37-7.31 (m, J = 6.1 Hz, 2H), 7.16-7.13 (m, 1H), 4.13 (t, J = 7.2 Hz, 2H), 3.91 (s, 3H), 3.80 (s, 8H), 2.70 (t, J = 7.2 Hz, 2H), 1.94-1.87 (m, 2H), 1.74-1.66 (m, 2H)

[0172] Example 3 (1-(5-methylhexyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone To a solution of 0.030 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.008 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.093 g of 1-bromo-5-methylhexane was then added, and the mixture was stirred at room temperature for 72 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 0.028 g of (1-(5-methylhexyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.52 (m, 1H), 7.83-7.83 (m, 1H), 7.67-7.64 (m, 1H), 7.18-7.14 (m, 1H), 4.13 (t, J = 7.2 Hz, 2H), 3.80 (s, 8H), 1.89-1.82 (m, 2H), 1.55-1.48 (m, 1H), 1.38-1.30 (m, 2H), 1.24-1.18 (m, 2H), 0.85 (d, J = 6.8 Hz, 6H)

[0173] Example 4 (1-(4-cyclopropylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone To a solution of 0.020 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 5 mL of N,N-dimethylformamide, 0.010 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.061 g of (4-bromobutyl)cyclopropane was then added, and the mixture was stirred at room temperature for 72 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a crude product. The crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to give 0.016 g of (1-(4-cyclopropylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.52 (m, 1H), 7.84 (s, 1H), 7.67-7.65 (m,1H), 7.18-7.15 (m, 1H), 4.13 (t, J = 7.2 Hz, 2H), 3.80 (s, 8H), 1.97-1.87 (m, 2H), 1.63 (s, 2H), 1.49-1.42 (m, 2H), 1.26-1.21 (m, 2H), 0.67-0.58 (m, 1H), 0.43-0.38 (m, 2H)

[0174] Example 5 (morpholin-4-yl)(1-((3-phenylcyclobutyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.05 g of 3-phenylcyclobutanecarboxylic acid in 1 mL of tetrahydrofuran, 0.035 mL of dimethyl sulfide borane was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at 0°C for 2 hours. The reaction mixture was then added dropwise to ice-cooled methanol, and the solvent was evaporated under reduced pressure. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.04 g of 3-phenylcyclobutylmethanol (dry 1:0.2). (2) To a solution of 0.04 g of 3-phenylcyclobutylmethanol in 2 mL of dichloromethane, 0.052 g of methanesulfonic anhydride and 0.085 mL of triethylamine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 2 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.023 g of crude (3-phenylcyclobutyl)methyl methanesulfonate. (3) To a solution of 0.02 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 2 mL of N,N-dimethylformamide, 0.004 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.021 g of crude (3-phenylcyclobutyl)methyl methanesulfonate was then added, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to give 0.006 g (dr 1:0.2) of (morpholin-4-yl)(1-((3-phenylcyclobutyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.52 (m, 1.2H), 7.88 (s, 0.2H), 7.83 (s, 1H), 7.72 (dd, J = 8.4, 1.6 Hz, 0.2H), 7.67 (dd, J = 8.4, 1.6 Hz, 1H), 7.31-7.28(m, 2.4H), 7.23-7.13 (m, 4.8H), 4.34 (d, J = 7.6 Hz, 0.4H), 4.16 (d, J = 7.2 Hz, 2H), 3.80 (s, 9.6H), 3.65-3.74 (m, 0.2H), 3.45-3.41 (m, 1H), 2.87-2.98 (m, 0.2H), 2.82-2.80 (m, 1H), 2.58-2.51 (m, 2H), 2.36-2.36 (m, 0.4H), 2.24-2.32 (m, 0.4H), 1.98-1.91 (m, 2H)

[0175] Example 6 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzonitrile (1) 0.980 g of 3-iodobenzonitrile, 0.068 g of copper(I) iodide, and 0.206 g of tetrakis(triphenylphosphine)palladium(0) were added to 7 mL of triethylamine and 0.250 g of 3-butyn-1-ol at room temperature under a nitrogen atmosphere and stirred at 70°C for 5 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.610 g of 3-(4-hydroxybut-1-yn-1-yl)benzonitrile. (2) To a solution of 0.670 g of 3-(4-hydroxybut-1-yn-1-yl)benzonitrile in 7 mL of dichloromethane, 1.13 g of triphenylphosphine and 1.43 g of carbon tetrabromide were added under a nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 4 hours. The solvent was then distilled off under reduced pressure to obtain a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=4:1). The solvent was then distilled off under reduced pressure to obtain 0.844 g of 3-(4-bromobut-1-yn-1-yl)benzonitrile. (3) 0.440 g of 3-(4-bromobut-1-yn-1-yl)benzonitrile was added with 0.158 g of palladium-fibroin under a nitrogen atmosphere, followed by the addition of 4 mL of ethanol and stirring at room temperature for 26 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 9:1), and the solvent was removed under reduced pressure to obtain 0.329 g of 3-(4-bromobutyl)benzonitrile. (4) To a solution of 0.020 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.005 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.041 g of 3-(4-bromobutyl)benzonitrile and 0.007 g of potassium iodide were then added, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was diluted with hexane. The mixture was separated using a 1:1 mixture of ethyl acetate and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=5:1), and the solvent was evaporated under reduced pressure to obtain 0.023 g of 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzonitrile. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54-8.53 (m, 1H), 7.81 (s, 1H), 7.63-7.61 (m,1H), 7.51-7.48 (m, 1H), 7.42 (s, 1H), 7.40-7.33 (m, 2H), 7.18-7.15 (m, 1H), 4.15 (t, J = 7.2Hz, 2H), 3.80 (s, 8H), 2.67 (t, J = 7.2 Hz, 2H), 1.95-1.87 (m, 2H),1.72-1.64 (m, 2H)

[0176] Example 7 (morpholin-4-yl)(1-((2-phenylcyclopropyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.361 mL of diiodomethane in 25 mL of dichloromethane, 2.795 mL of diethylzinc (1 mol / L toluene solution) was added at 0°C under a nitrogen atmosphere. Furthermore, to a solution of 0.3 g of (2E)-3-phenylpropyl-2-en-1-ol in 7 mL of dichloromethane prepared in a separate flask, 2.795 mL of diethylzinc (1 mol / L toluene solution) was added at 0°C under a nitrogen atmosphere. After stirring at 0°C for 30 minutes, the mixture was added dropwise to the first flask and stirred at room temperature for 23 hours. Saturated aqueous ammonium chloride was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.282 g of (2-phenylcyclopropyl)methanol. (2) To a solution of 0.07 g of (2-phenylcyclopropyl)methanol in 2 mL of dichloromethane, 0.099 g of methanesulfonic anhydride and 0.164 mL of triethylamine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 30 minutes. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.108 g of crude (2-phenylcyclopropyl)methyl methanesulfonate. (3) To a solution of 0.1 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 2 mL of N,N-dimethylformamide, 0.043 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.108 g of crude (2-phenylcyclopropyl)methyl methanesulfonate was then added, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was distilled off under reduced pressure to obtain 0.035 g (dr 1:1) of (morpholin-4-yl)(1-((2-phenylcyclopropyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.55-8.53 (m, 2H), 7.95 (s, 2H), 7.72-7.69 (m,2H), 7.27-7.24 (m, 4H), 7.19-7.15 (m, 4H), 7.04-7.01 (m, 4H), 4.26 (dd, J = 14.4, 6.4 Hz, 2H), 4.10 (dd, J = 14.4, 7.2 Hz, 2H), 3.80 (s, 16H), 2.02-1.98 (m, 2H), 1.62-1.57 (m, 2H), 1.18-1.13 (m, 2H), 1.12-1.07 (m, 2H)

[0177] Example 8 (morpholin-4-yl)(1-((3-phenylcyclopentyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.6 g of 4-phenylcyclohexan-1-one in 8 mL of dichloromethane, 0.697 g of sulfuryl chloride was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 3 hours. Saturated aqueous sodium bicarbonate was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.155 g of 2-chloro-4-phenylcyclohexan-1-one (dr 1:0.4). (2) To a solution of 0.15 g of 2-chloro-4-phenylcyclohexan-1-one in 6 mL of diethyl ether, 0.043 g of sodium methoxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 2.5 hours. Then, 3 mol / L aqueous hydrochloric acid was added, and the mixture was separated using diethyl ether. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.062 g of 3-phenylcyclopentane-1-methyl ester. (3) To a solution of 0.1 g of 3-phenylcyclopentane-1-methyl ester in 2 mL of toluene, 0.272 mL of sodium bis(2-methoxyethoxy)aluminum hydride (70% toluene solution, approximately 3.6 mol / L) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 30 minutes. A saturated aqueous solution of potassium sodium tartrate was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.057 g of (3-phenylcyclopentyl)methanol. (4) To a solution of 0.057 g of (3-phenylcyclopentyl)methanol in 2 mL of dichloromethane, 0.068 g of methanesulfonic anhydride and 0.112 mL of triethylamine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 30 minutes. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.044 g of crude (3-phenylcyclopentyl)methyl methanesulfonate. (5) To a solution of 0.04 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 2 mL of N,N-dimethylformamide, 0.017 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.044 g of crude (3-phenylcyclopentyl)methyl methanesulfonate was then added, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by preparative thin-layer chromatography (hexane, ethyl acetate, and methanol = 5:5:1), and the solvent was removed under reduced pressure to obtain 0.009 g of (morpholin-4-yl)(1-((3-phenylcyclopentyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (dr 1:1). 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54-8.52 (m, 2H), 7.87 (s, 2H), 7.71-7.69 (m,2H), 7.30-7.26 (m, 4H), 7.20-7.15 (m, 8H), 4.15 (dd, J = 14.0, 7.6 Hz, 2H), 4.09 (dd, J = 13.2, 7.2 Hz, 2H), 3.80 (s, 16H), 3.26-3.17 (m, 2H), 2.79-2.72 (m, 2H), 2.23-2.15 (m, 2H), 2.04-1.96 (m, 2H), 1.89-1.83 (m, 4H), 1.76-1.68 (m, 2H), 1.50-1.41 (m, 2H)

[0178] Example 9 (1-(4-(2-chlorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) 0.600 g of 3-butyn-1-ol, 0.049 g of copper(I) iodide, and 0.148 g of tetrakis(triphenylphosphine)palladium(0) were added to 20 mL of triethylamine and 2.12 g of 1-chloro-2-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50°C for 6 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 1.49 g of 4-(2-chlorophenyl)-3-butyn-1-ol. (2) To a solution of 1.40 g of 4-(2-chlorophenyl)-3-butyn-1-ol in 10 mL of dichloromethane, 3.09 g of carbon tetrabromide and 2.44 g of triphenylphosphine were added under a nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 3 hours. The solvent was then distilled off under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was then distilled off under reduced pressure to obtain 1.87 g of 1-(4-bromobut-1-yn-1-yl)-2-chlorobenzene. (3) 0.069 g of palladium-fibroin was added to 0.200 g of 1-(4-bromobut-1-yn-1-yl)-2-chlorobenzene under a nitrogen atmosphere, followed by the addition of 10 mL of methanol and stirring at room temperature for 24 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 0.181 g of 1-(4-bromobutyl)-2-chlorobenzene. (4) To a solution of 0.015 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.004 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. Further, 0.032 g of 1-(4-bromobutyl)-2-chlorobenzene and 0.005 g of potassium iodide were added, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.005 g of (1-(4-(2-chlorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.44-8.42 (m, 1H), 7.99-7.93 (m, 2H), 7.31-7.25(m, 2H), 7.23-7.12 (m, 3H), 4.31 (t, J = 7.2 Hz, 2H), 3.72 (s, 8H), 2.80-2.60 (m, 2H), 1.97-1.90 (m, 2H), 1.65-1.57 (m, 2H)

[0179] Example 10 (1-(4-(2-fluorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) 1.20 g of 3-butyn-1-ol, 0.098 g of copper(I) iodide, and 0.297 g of tetrakis(triphenylphosphine)palladium(0) were added to 30 mL of triethylamine and 3.80 g of 1-fluoro-2-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50 °C for 24 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 2.47 g of 4-(2-fluorophenyl)-3-butyn-1-ol. (2) To a solution of 2.49 g of 4-(2-fluorophenyl)-3-butyn-1-ol in 30 mL of dichloromethane, 6.04 g of carbon tetrabromide and 4.77 g of triphenylphosphine were added under a nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 23 hours. The crude product obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was then distilled off under reduced pressure to obtain 2.90 g of 1-(4-bromobut-1-yn-1-yl)-2-fluorobenzene. (3) 0.688 g of palladium-fibroin was added to 0.930 g of 1-(4-bromobut-1-yn-1-yl)-2-fluorobenzene under a nitrogen atmosphere, followed by the addition of 30 mL of methanol and stirring at room temperature for 46 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to obtain 0.629 g of 1-(4-bromobutyl)-2-fluorobenzene. (4) To a solution of 0.020 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.005 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.040 g of 1-(4-bromobutyl)-2-fluorobenzene and 0.007 g of potassium iodide were then added, and the mixture was stirred at room temperature for 19 hours. Water was then added, and the mixture was diluted with hexane: The mixture was separated using ethyl acetate (1:1). The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain a crude product. The resulting crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was distilled off under reduced pressure to obtain 0.006 g of (1-(4-(2-fluorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.97-7.95 (m, 1H), 7.91 (s, 1H), 7.28-7.25 (m, 1H), 7.19-7.15 (m, 2H), 7.06-6.96 (m, 2H), 4.31 (t, J = 7.2 Hz, 2H), 3.72 (s, 8H), 2.67 (t, J = 7.6 Hz, 2H), 1.94-1.87 (m, 2H), 1.65-1.58 (m,2H)

[0180] Example 11 (1-(4-(3-fluorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) 1.00 g of 3-butyn-1-ol, 0.082 g of copper(I) iodide, and 0.247 g of tetrakis(triphenylphosphine)palladium(0) were added to 30 mL of triethylamine and 3.17 g of 1-fluoro-3-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50 °C for 3 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 1.91 g of 4-(3-fluorophenyl)-3-butyn-1-ol. (2) To a solution of 1.90 g of 4-(3-fluorophenyl)-3-butyn-1-ol in 30 mL of dichloromethane, 4.61 g of carbon tetrabromide and 3.64 g of triphenylphosphine were added under a nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 24 hours. The crude product obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was then distilled off under reduced pressure to obtain 2.45 g of 1-(4-bromobut-1-yn-yl)-3-fluorobenzene. (3) 1.00 g of 1-(4-bromobut-1-yn-yl)-3-fluorobenzene was added with 0.740 g of palladium-fibroin under a nitrogen atmosphere, followed by addition of 30 mL of methanol and stirring at room temperature for 46 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 0.896 g of 1-(4-bromobutyl)-3-fluorobenzene. (4) To a solution of 0.020 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.005 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. Further, 0.040 g of 1-(4-bromobutyl)-3-fluorobenzene and 0.007 g of potassium iodide were added, and the mixture was stirred at room temperature for 19 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.014 g of (1-(4-(3-fluorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.44-8.42 (m, 1H), 7.98-7.95 (m, 1H), 7.92 (s, 1H), 7.28-7.20 (m, 2H), 6.95-6.93 (m, 1H), 6.88-6.83 (m, 2H), 4.30 (t, J = 7.2 Hz, 2H), 3.72 (s, 8H), 2.64 (t, J = 7.6 Hz, 2H), 1.93-1.85 (m, 2H), 1.66-1.58 (m,2H)

[0181] Example 12 (1-(6-methylheptyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholin-4-yl)methanone (1) To a solution of 0.24 g of 6-methylheptanoic acid in 4 mL of toluene, 0.925 mL of sodium bis(2-methoxyethoxy)aluminum hydride (70% toluene solution, approximately 3.6 mol / L) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1.5 hours. A saturated aqueous solution of potassium sodium tartrate was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.101 g of 6-methylheptan-1-ol. (2) To a solution of 0.1 g of 6-methylheptan-1-ol in 3 mL of dichloromethane, 0.161 g of methanesulfonic anhydride and 0.266 mL of triethylamine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1 hour. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.116 g of crude 6-methylheptane methanesulfonate. (3) To a solution of 0.1 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.043 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.09 g of crude 6-methylheptane methanesulfonate was then added, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.032 g of (1-(6-methylheptyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholin-4-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54 (d, J = 4.8 Hz, 1H), 7.85 (s, 1H), 7.67 (d, J = 8.4 Hz, 1H), 7.17 (dd, J = 8.4, 4.8 Hz, 1H), 4.14 (t, J = 7.6 Hz, 2H), 3.82 (s, 8H), 1.90-1.87 (m, 2H), 1.53-1.48 (m, 1H), 1.35-1.31 (m, 4H), 1.18-1.15 (m, 2H), 0.86 (d, J = 6.4 Hz, 6H)

[0182] Example 13 Morpholino(1-((trans-4-phenylcyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.1 g of trans-4-phenylcyclohexane-1-carboxylic acid in 1 mL of toluene, 0.272 mL of sodium bis(2-methoxyethoxy)aluminum hydride (70% toluene solution, approximately 3.6 mol / L) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1.5 hours. A saturated aqueous solution of potassium sodium tartrate was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.06 g of (trans-4-phenylcyclohexyl)methanol. (2) To a solution of 0.1 g of (trans-4-phenylcyclohexyl)methanol in 2 mL of dichloromethane, 0.11 g of methanesulfonic anhydride and 0.182 mL of triethylamine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1 hour. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to obtain 0.052 g of a crude product of (trans-4-phenylcyclohexyl)methyl methanesulfonate. (3) To a solution of 0.05 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 2 mL of N,N-dimethylformamide, 0.022 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.058 g of crude (trans-4-phenylcyclohexyl)methyl methanesulfonate was then added, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.007 g of morpholino(1-((trans-4-phenylcyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53 (dd, J = 4.4, 1.2 Hz, 1H), 7.83 (s, 1H), 7.68 (dd, J = 8.4, 1.2 Hz, 1H), 7.30-7.26 (m, 3H), 7.20-7.16 (m, 3H), 4.03 (d, J= 7.2 Hz, 2H), 3.82 (s, 8H), 2.50-2.46 (m, 1H), 1.95-1.91 (m, 2H), 1.82-1.79 (m, 2H), 1.46-1.39 (m, 2H), 1.28-1.21 (m, 2H), 0.86-0.86 (m, 1H)

[0183] Example 14 (1-(4-methylpentyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholin-4-yl)methanone To a solution of 0.07 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 2 mL of N,N-dimethylformamide, 0.03 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.06 g of 1-bromo-4-methylpentane was then added, and the mixture was stirred at room temperature for 19 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 0.041 g of (1-(4-methylpentyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholin-4-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53 (d, J = 4.8 Hz, 1H), 7.84 (s, 1H), 7.66 (d, J = 8.0 Hz, 1H), 7.17 (dd, J = 8.4, 4.8 Hz, 1H), 4.11 (t, J = 7.2 Hz, 2H), 3.81 (s, 8H), 1.91-1.84 (m, 2H), 1.61-1.55 (m, 1H), 1.26-1.21 (m, 2H), 0.88 (dd, J= 6.4, 0.8 Hz, 6H)

[0184] Example 15 (1-(4-(4-fluorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) 1.00 g of 3-butyn-1-ol, 0.082 g of copper(I) iodide, and 0.247 g of tetrakis(triphenylphosphine)palladium(0) were added to 30 mL of triethylamine and 3.17 g of 1-fluoro-4-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50 °C for 27 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 2.14 g of 4-(4-fluorophenyl)-3-butyn-1-ol. (2) To a solution of 2.10 g of 4-(4-fluorophenyl)-3-butyn-1-ol in 30 mL of dichloromethane, 5.09 g of carbon tetrabromide and 4.03 g of triphenylphosphine were added under a nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 24 hours. The solvent was then distilled off under reduced pressure to obtain a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1). The solvent was then distilled off under reduced pressure to obtain 1.87 g of 1-(4-bromobut-1-yn-1-yl)-4-fluorobenzene. (3) 0.900 g of 1-(4-bromobut-1-yn-1-yl)-4-fluorobenzene was added with 0.666 g of palladium-fibroin under a nitrogen atmosphere, followed by addition of 30 mL of methanol and stirring at room temperature for 46 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 0.910 g of 1-(4-bromobutyl)-4-fluorobenzene. (4) To a solution of 0.025 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.006 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature and stirred for 30 minutes. 0.050 g of 1-(4-bromobutyl)-4-fluorobenzene and 0.009 g of potassium iodide were then added and stirred at room temperature for 19 hours. Water was then added, and the mixture was separated using hexane:ethyl acetate=1:1. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 0.028 g of (1-(4-(4-fluorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.44-8.42 (m, 1H), 7.97-7.95 (m, 1H), 7.92 (s, 1H), 7.28-7.25 (m, 1H), 7.14-7.11 (m, 2H), 6.96-6.91 (m, 2H), 4.30 (t, J = 7.2 Hz, 2H), 3.72 (s, 8H), 2.61 (t, J = 7.6 Hz, 2H), 1.90-1.84 (m, 2H), 1.64-1.58 (m,2H)

[0185] Example 16 (1-(4-(3-chlorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) 0.250 g of 3-butyn-1-ol, 0.034 g of copper(I) iodide, and 0.206 g of tetrakis(triphenylphosphine)palladium(0) were added to 20 mL of triethylamine and 0.851 g of 1-chloro-3-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50°C for 24 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.520 g of 4-(3-chlorophenyl)-3-butyn-1-ol. (2) 0.504 g of 4-(3-chlorophenyl)-3-butyn-1-ol was added with 0.234 g of palladium-fibroin under a nitrogen atmosphere, followed by the addition of 10 mL of methanol and stirring at room temperature for 24 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 0.489 g of 1-(4-hydroxybutyl)-3-chlorobenzene. (3) To a solution of 0.100 g of 1-(4-hydroxybutyl)-3-chlorobenzene in 5 mL of dichloromethane, 0.113 g of methanesulfonic anhydride, 0.188 mL of triethylamine, and 0.007 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.051 g of crude 4-(3-chlorophenyl)butyl methanesulfonate. (4) To a solution of 0.045 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.019 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.051 g of crude 4-(3-chlorophenyl)butyl methanesulfonate and 0.016 g of potassium iodide were then added, and the mixture was stirred at room temperature for 20 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.052 g of (1-(4-(3-chlorophenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.44-8.43 (m, 1H), 7.98-7.92 (m, 2H), 7.29-7.05(m, 5H), 4.30 (t, J = 7.2 Hz, 2H), 3.72 (s, 8H), 2.62 (t, J = 7.2 Hz, 2H), 1.92-1.85 (m, 2H), 1.65-1.58 (m, 2H)

[0186] Example 17 (1-(4-(2-Methoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) 0.400 g of 3-butyn-1-ol, 0.033 g of copper(I) iodide, and 0.099 g of tetrakis(triphenylphosphine)palladium(0) were added to 20 mL of triethylamine and 1.34 g of 2-iodoanisole at room temperature under a nitrogen atmosphere and stirred at 50°C for 24 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.625 g of 4-(2-methoxyphenyl)-3-butyn-1-ol. (2) 0.795 g of palladium-fibroin was added to 0.500 g of 4-(2-methoxyphenyl)-3-butyn-1-ol under a nitrogen atmosphere, followed by the addition of 10 mL of methanol and stirring at room temperature for 24 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 0.460 g of 4-(2-methoxyphenyl)butan-1-ol. (3) To a solution of 0.100 g of 4-(2-methoxyphenyl)butan-1-ol in 3 mL of dichloromethane, 0.116 g of methanesulfonic anhydride, 0.192 mL of triethylamine, and 0.007 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.051 g of crude 4-(2-methoxyphenyl)butyl methanesulfonate. (4) To a solution of 0.046 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.020 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.051 g of crude 4-(2-methoxyphenyl)butyl methanesulfonate and 0.017 g of potassium iodide were then added, and the mixture was stirred at room temperature for 20 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.050 g of (1-(4-(2-methoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.41 (m, 1H), 7.94-7.92 (m, 1H), 7.90 (s, 1H), 7.27-7.24 (m, 1H), 7.14-7.10 (m, 1H), 7.04-7.02 (m, 1H), 6.87-6.85 (m, 1H),6.82-6.78 (m, 1H), 4.27 (t, J = 7.2 Hz, 2H), 3.73 (s, 3H), 3.71 (s, 8H), 2.61 (t, J = 7.6 Hz, 2H), 1.90-1.83 (m, 2H), 1.60-1.52 (m, 2H)

[0187] Example 18 (1-(4-(3-Methoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) 0.400 g of 3-butyn-1-ol, 0.054 g of copper(I) iodide, and 0.200 g of dichlorobis(triphenylphosphine)palladium(II) were added to 20 mL of triethylamine and 1.34 g of 3-iodoanisole at room temperature under a nitrogen atmosphere and stirred at 50°C for 24 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.625 g of 4-(3-methoxyphenyl)-3-butyn-1-ol. (2) 0.625 g of 4-(3-methoxyphenyl)-3-butyn-1-ol was added with 0.993 g of palladium-fibroin under a nitrogen atmosphere, followed by the addition of 10 mL of methanol and stirring at room temperature for 48 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 0.505 g of 1-(4-hydroxybutyl)-3-methoxybenzene. (3) To a solution of 0.100 g of 1-(4-hydroxybutyl)-3-methoxybenzene in 3 mL of dichloromethane, 0.116 g of methanesulfonic anhydride, 0.192 mL of triethylamine, and 0.007 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. Then, water was added, and The mixture was separated using dichloromethane, and the resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain 0.080 g of a crude product of 4-(3-methoxyphenyl)butyl methanesulfonate. (4) To a solution of 0.046 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.020 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.051 g of crude 4-(3-methoxyphenyl)butyl methanesulfonate and 0.017 g of potassium iodide were then added, and the mixture was stirred at room temperature for 20 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.049 g of (1-(4-(3-methoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.95-7.93 (m, 1H), 7.91 (s, 1H), 7.28-7.24 (m, 1H), 7.14-7.10 (m, 1H), 6.70-6.67 (m, 3H), 4.28 (t, J = 6.8 Hz, 2H), 3.72-3.72 (m, 11H), 2.59 (t, J = 7.6 Hz, 2H), 1.91-1.84 (m, 2H), 1.64-1.57 (m, 2H)

[0188] Example 19 (1-(4-(4-Methoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) 0.400 g of 3-butyn-1-ol, 0.054 g of copper(I) iodide, and 0.200 g of dichlorobis(triphenylphosphine)palladium(II) were added to 20 mL of triethylamine and 1.34 g of 4-iodoanisole at room temperature under a nitrogen atmosphere and stirred at 50°C for 24 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.158 g of 4-(4-methoxyphenyl)-3-butyn-1-ol. (2) 0.158 g of 4-(4-methoxyphenyl)-3-butyn-1-ol was added with 0.075 g of palladium-fibroin under a nitrogen atmosphere, followed by the addition of 10 mL of methanol and stirring at room temperature for 48 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 0.138 g of 1-(4-hydroxybutyl)-4-methoxybenzene. (3) To a solution of 0.100 g of 1-(4-hydroxybutyl)-4-methoxybenzene in 10 mL of dichloromethane, 0.116 g of methanesulfonic anhydride, 0.192 mL of triethylamine, and 0.007 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 2 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.084 g of crude 4-(4-methoxyphenyl)butyl methanesulfonate. (4) To a solution of 0.045 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.019 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.050 g of crude 4-(4-methoxyphenyl)butyl methanesulfonate and 0.016 g of potassium iodide were then added, and the mixture was stirred at room temperature for 18 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.054 g of (1-(4-(4-methoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.94-7.93 (m, 1H), 7.90 (s, 1H), 7.28-7.24 (m, 1H), 7.03-7.01 (m, 2H), 6.79-6.77 (m, 2H), 4.27 (t, J = 6.8 Hz, 2H), 3.73 (s, 11H), 2.56 (t, J = 7.6 Hz, 2H), 1.90-1.83 (m, 2H), 1.62-1.54 (m, 2H)

[0189] Example 20 (morpholin-4-yl)(1-(3-phenoxypropyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.1 g of phenol in 3 mL of N,N-dimethylformamide, 0.051 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred for 30 minutes. 0.323 g of (3-bromopropoxy)(tert-butyl)dimethylsilane was then added, and the mixture was stirred at room temperature for 1 hour. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=9:1), and the solvent was evaporated under reduced pressure to obtain 0.284 g of tert-butyldimethyl(3-phenoxypropoxy)silane. (2) To a solution of 0.28 g of tert-butyldimethyl(3-phenoxypropoxy)silane in 2 mL of tetrahydrofuran, 0.33 mL of tetrabutylammonium fluoride (approximately 1 mol / L tetrahydrofuran solution) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 2 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.196 g of 3-phenoxypropan-1-ol. (3) To a solution of 0.16 g of 3-phenoxypropan-1-ol in 2 mL of dichloromethane, 0.22 g of methanesulfonic anhydride and 0.364 mL of triethylamine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.221 g of crude 3-phenoxypropyl methanesulfonate. (4) To a solution of 0.2 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 4 mL of N,N-dimethylformamide, 0.038 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.219 g of crude 3-phenoxypropyl methanesulfonate was then added, and the mixture was stirred at room temperature for 18 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.057 g of (morpholin-4-yl)(1-(3-phenoxypropyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.51 (dd, J = 4.8, 1.2 Hz, 1H), 7.83 (s, 1H), 7.68 (dd, J = 8.0, 1.2 Hz, 1H), 7.30-7.26 (m, 2H), 7.10 (dd, J = 8.0, 4.8 Hz, 1H), 6.97 (t, J = 7.6 Hz, 1H), 6.86 (d, J = 7.6 Hz, 2H), 4.40 (t, J = 6.8 Hz, 2H),3.91 (t, J = 5.6 Hz, 2H), 3.77 (s, 8H), 2.35-2.29 (m, 2H)

[0190] Example 21 (1-(4-(2,3-dimethoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) To 0.758 g of magnesium, 1 grain of iodine, 9 mL of tetrahydrofuran, and 0.758 g of benzyl 3-bromopropyl ether were added under a nitrogen atmosphere at 0°C and stirred at room temperature for 6 hours to prepare a Grignard reagent. Subsequently, the Grignard reagent was added to a solution of 0.5 g of 2,3-dimethoxybenzaldehyde in 9 mL of tetrahydrofuran under a nitrogen atmosphere at 0°C and stirred at room temperature for 16 hours. Saturated aqueous ammonium chloride was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.485 g of 4-(benzyloxy)-1-(2,3-dimethoxyphenyl)butan-1-ol. (2) To a solution of 0.485 g of 4-(benzyloxy)-1-(2,3-dimethoxyphenyl)butan-1-ol in 10 mL of dichloromethane, 0.124 mL of boron trifluoride diethyl ether complex and 0.315 mL of triethylsilane were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 19 hours. Saturated aqueous sodium bicarbonate solution was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.152 g of 1-(4-(benzyloxy)butyl)-2,3-dimethoxybenzene. (3) To 0.152 g of 1-(4-(benzyloxy)butyl)-2,3-dimethoxybenzene, 0.027 g of palladium-carbon was added under a nitrogen atmosphere, followed by the addition of 3 mL of methanol and stirring at room temperature for 3 hours under a hydrogen atmosphere. The mixture was then filtered through Celite, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then distilled off under reduced pressure to obtain 0.108 g of 4-(2,3-dimethoxyphenyl)butan-1-ol. (4) To a solution of 0.108 g of 4-(2,3-dimethoxyphenyl)butan-1-ol in 5 mL of dichloromethane, 0.107 g of methanesulfonic anhydride, 0.177 mL of triethylamine, and 0.006 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.123 g of 4-(2,3-dimethoxyphenyl)butyl methanesulfonate. (5) To a solution of 0.049 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.013 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.061 g of 4-(2,3-dimethoxyphenyl)butyl methanesulfonate was then added, and the mixture was stirred at room temperature for 15 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.025 g of (1-(4-(2,3-dimethoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.52-8.50 (m, 1H), 7.81 (s, 1H), 7.65-7.63 (m, 1H), 7.16-7.13 (m, 1H), 6.97 (t, J = 8.0 Hz, 1H), 6.79-6.77 (m, 1H), 6.72-6.69 (m, 1H), 4.13 (t, J = 7.2 Hz, 2H), 3.86 (s, 3H), 3.80-3.78 (m, 11H), 2.67 (t, J = 7.2 Hz, 2H), 1.93-1.86 (m, 2H), 1.68-1.61 (m, 2H)

[0191] Example 22 (1-(4-(2,5-dimethoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) To 0.758 g of magnesium, 1 grain of iodine, 9 mL of tetrahydrofuran, and 0.758 g of benzyl 3-bromopropyl ether were added under a nitrogen atmosphere at 0°C and stirred at room temperature for 6 hours to prepare a Grignard reagent. Subsequently, the Grignard reagent was added to a solution of 0.5 g of 2,5-dimethoxybenzaldehyde in 9 mL of tetrahydrofuran under a nitrogen atmosphere at 0°C and stirred at room temperature for 16 hours. Saturated aqueous ammonium chloride was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.391 g of 4-(benzyloxy)-1-(2,5-dimethoxyphenyl)butan-1-ol. (2) To a solution of 0.391 g of 4-(benzyloxy)-1-(2,5-dimethoxyphenyl)butan-1-ol in 10 mL of dichloromethane, 0.124 mL of boron trifluoride diethyl ether complex and 0.315 mL of triethylsilane were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 18 hours. Saturated aqueous sodium bicarbonate solution was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.105 g of 2-(4-(benzyloxy)butyl)-1,4-dimethoxybenzene. (3) To 0.105 g of 2-(4-(benzyloxy)butyl)-1,4-dimethoxybenzene, 0.019 g of palladium-carbon was added under a nitrogen atmosphere, followed by the addition of 3 mL of methanol, and the mixture was stirred at room temperature under a hydrogen atmosphere for 15.5 hours. The mixture was then filtered through Celite, and the resulting crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate=2:1). The solvent was then distilled off under reduced pressure to obtain 0.075 g of 4-(2,5-dimethoxyphenyl)butan-1-ol. (4) To a solution of 0.075 g of 4-(2,5-dimethoxyphenyl)butan-1-ol in 5 mL of dichloromethane, 0.075 g of methanesulfonic anhydride, 0.124 mL of triethylamine, and 0.004 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.085 g of 4-(2,5-dimethoxyphenyl)butyl methanesulfonate. (5) To a solution of 0.034 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.009 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.042 g of 4-(2,5-dimethoxyphenyl)butyl methanesulfonate was then added, and the mixture was stirred at room temperature for 15 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.015 g of (1-(4-(2,5-dimethoxyphenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.52-8.51 (m, 1H), 7.82 (s, 1H), 7.65-7.62 (m, 1H), 7.16-7.13 (m, 1H), 6.78-6.75 (m, 1H), 6.71-6.66 (m, 2H), 4.14 (t, J = 7.4 Hz, 2H), 3.80 (s, 8H), 3.75 (s, 3H), 3.75 (s, 3H), 2.63 (t, J = 7.6 Hz, 2H), 1.94-1.87 (m, 2H), 1.67-1.60 (m, 2H)

[0192] Example 23 (1-(4-cyclohexylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) To a solution of 0.125 g of 4-cyclohexylbutan-1-ol in 5 mL of dichloromethane, 0.167 g of methanesulfonic anhydride, 0.277 mL of triethylamine, and 0.010 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 26 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.146 g of crude 4-cyclohexylbutyl methanesulfonate. (2) To a solution of 0.045 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 5 mL of N,N-dimethylformamide, 0.019 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.146 g of crude 4-cyclohexylbutyl methanesulfonate was then added, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.063 g of (1-(4-cyclohexylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.44-8.43 (m, 1H), 8.01-7.98 (m, 1H), 7.93 (s, 1H), 7.30-7.27 (m, 1H), 4.28 (t, J = 6.8 Hz, 2H), 3.73 (s, 8H), 1.88-1.81 (m, 2H), 1.66-1.65 (m, 5H), 1.35-1.12 (m, 8H), 0.88-0.80 (m, 2H)

[0193] Example 24 1-(4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)ethanone (1) 0.500 g of 3-butyn-1-ol, 0.102 g of copper(I) iodide, and 0.376 g of dichlorobis(triphenylphosphine)palladium(II) were added to 20 mL of triethylamine and 2.63 g of 4-iodoacetophenone under a nitrogen atmosphere at room temperature, and the mixture was stirred at 50°C for 19 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 1.25 g of 1-(4-(4-hydroxy-1-butyn-1-yl)phenyl)ethan-1-one. (2) 1.25 g of 1-(4-(4-hydroxybut-1-yn-1-yl)phenyl)ethan-1-one was added with 0.558 g of palladium-fibroin under a nitrogen atmosphere, followed by addition of 30 mL of methanol and stirring at room temperature for 48 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to obtain 1.09 g of 1-(4-(4-hydroxybutyl)phenyl)ethan-1-one. (3) To a solution of 0.250 g of 1-(4-(4-hydroxybutyl)phenyl)ethan-1-one in 5 mL of dichloromethane, 0.272 g of methanesulfonic anhydride, 0.451 mL of triethylamine, and 0.016 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1 hour. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.295 g of crude 4-(4-acetylphenyl)butyl methanesulfonate. (4) To a solution of 0.257 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 5 mL of N,N-dimethylformamide, 0.111 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.295 g of crude 4-(4-acetylphenyl)butyl methanesulfonate was then added, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and then the solvent was distilled off under reduced pressure to obtain 0.095 g of 1-(4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)ethanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.41 (m, 1H), 7.96-7.94 (m, 1H), 7.92 (s, 1H), 7.79-7.77 (m, 1H), 7.75 (s, 1H), 7.40-7.34 (m, 2H), 7.26-7.23 (m, 1H), 4.30 (t, J = 7.2 Hz, 2H), 3.71 (s, 8H), 2.69 (t, J = 7.6 Hz, 2H), 2.55 (s, 3H), 1.93-1.86 (m, 2H), 1.68-1.60 (m, 2H)

[0194] Example 25 1-(3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)ethanone (1) 0.500 g of 3-butyn-1-ol, 0.102 g of copper(I) iodide, and 0.376 g of dichlorobis(triphenylphosphine)palladium(II) were added to 30 mL of triethylamine and 2.63 g of 3-iodoacetophenone at room temperature under a nitrogen atmosphere and stirred at 50°C for 19 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 1.28 g of 1-(3-(4-hydroxybut-1-yn-1-yl)phenyl)ethan-1-one. (2) 0.535 g of palladium-fibroin was added to 1.20 g of 1-(3-(4-hydroxybut-1-yn-1-yl)phenyl)ethan-1-one under a nitrogen atmosphere, followed by the addition of 30 mL of methanol and stirring at room temperature for 30 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to obtain 0.997 g of 1-(3-(4-hydroxybutyl)phenyl)ethan-1-one. (3) To a solution of 0.250 g of 1-(3-(4-hydroxybutyl)phenyl)ethan-1-one in 5 mL of dichloromethane, 0.272 g of methanesulfonic anhydride, 0.451 mL of triethylamine, and 0.016 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1 hour. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.305 g of crude 4-(3-acetylphenyl)butyl methanesulfonate. (4) To a solution of 0.257 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 5 mL of N,N-dimethylformamide, 0.111 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.300 g of crude 4-(3-acetylphenyl)butyl methanesulfonate was then added, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and then the solvent was distilled off under reduced pressure to obtain 0.113 g of 1-(3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)ethanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.97-7.94 (m, 1H), 7.92 (s, 1H), 7.88-7.86 (m, 2H), 7.28-7.24 (m, 3H), 4.30 (t, J = 7.2 Hz, 2H), 3.72 (s, 8H), 2.71 (t, J = 7.6 Hz, 2H), 2.56 (s, 3H), 1.94-1.86 (m, 2H), 1.69-1.61 (m, 2H)

[0195] Example 26 2-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid methyl ester (1) 1.50 g of 3-butyn-1-ol, 0.122 g of copper(I) iodide, and 40.1 g of tetrakis(triphenylphosphine)palladium(0) were added to 20 mL of triethylamine and 5.31 g of 2-(methoxycarbonyl)-1-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50°C for 17 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 3.87 g of methyl 2-(4-hydroxybut-1-yn-1-yl)benzoate. (2) To a solution of 3.80 g of methyl 2-(4-hydroxybut-1-yn-1-yl)benzoate in 30 mL of dichloromethane, 6.79 g of carbon tetrabromide and 5.37 g of triphenylphosphine were added under a nitrogen atmosphere at 0° C., and the mixture was stirred at room temperature for 2 hours. The solvent was then distilled off under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then distilled off under reduced pressure to obtain 4.03 g of methyl 2-(4-bromobut-1-yn-1-yl)benzoate. (3) 2.08 g of palladium-fibroin was added to 3.30 g of methyl 2-(4-bromobut-1-yn-1-yl)benzoate under a nitrogen atmosphere, followed by the addition of 10 mL of methanol and stirring at room temperature for 48 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 3.19 g of methyl 2-(4-bromobutyl)benzoate. (4) To a solution of 0.040 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.010 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. Further, 0.047 g of methyl 2-(4-bromobutyl)benzoate and 0.014 g of potassium iodide were added, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and then the solvent was distilled off under reduced pressure to obtain 0.010 g of methyl 2-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoate. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.99-7.97 (m, 1H), 7.93 (s, 1H), 7.81-7.79 (m, 1H), 7.43-7.40 (m, 1H), 7.29-7.23 (m, 3H), 4.31 (t, J = 6.8 Hz, 2H), 3.77 (s, 3H), 3.71 (s, 8H), 2.96 (t, J = 7.6 Hz, 2H), 1.96-1.89 (m, 2H), 1.61-1.53 (m, 2H)

[0196] Example 27 4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid methyl ester (1) 1.00 g of 3-butyn-1-ol, 0.082 g of copper(I) iodide, and 0.247 g of tetrakis(triphenylphosphine)palladium(0) were added to 30 mL of triethylamine and 3.54 g of 4-(methoxycarbonyl)-1-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50°C for 18 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 5.28 g of methyl 4-(4-hydroxybut-1-yn-1-yl)benzoate. (2) To a solution of 5.00 g of methyl 4-(4-hydroxybut-1-yn-1-yl)benzoate in 30 mL of dichloromethane, 9.74 g of carbon tetrabromide and 7.71 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 24 hours. The solvent was then distilled off under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then distilled off under reduced pressure to obtain 1.72 g of methyl 4-(4-bromobut-1-yn-1-yl)benzoate. (3) 1.25 g of methyl 4-(4-bromobut-1-yn-1-yl)benzoate was added to 0.786 g of palladium-fibroin under a nitrogen atmosphere, followed by 30 mL of methanol and stirring at room temperature for 19 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to give 1.24 g of methyl 4-(4-bromobutyl)benzoate. (4) To a solution of 0.040 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.010 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. Further, 0.094 g of methyl 4-(4-bromobutyl)benzoate and 0.014 g of potassium iodide were added, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and then the solvent was distilled off under reduced pressure to obtain 0.010 g of methyl 4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoate. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.41 (m, 1H), 7.97-7.87 (m, 4H), 7.28-7.23 (m, 3H), 4.30 (t, J = 6.8 Hz, 2H), 3.87 (s, 3H), 3.72 (s, 8H), 2.70 (t, J = 7.6 Hz, 2H), 1.93-1.86 (m, 2H), 1.68-1.61 (m, 2H)

[0197] Example 28 (morpholin-4-yl)(1-(2-(2-phenylcyclopropyl)ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.27 g of (2-phenylcyclopropyl)methanol in 4 mL of dichloromethane, 0.811 g of Dess-Martin periodinane was added at 0°C under a nitrogen atmosphere and stirred at room temperature for 1.5 hours. Saturated aqueous sodium thiosulfate was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.223 g of 2-phenylcyclopropane-1-carboxaldehyde (dry 1:1). (2) To a solution of 0.567 g of (methoxymethyl)triphenylphosphonium chloride in 5 mL of tetrahydrofuran, 1.035 mL of n-butyllithium (1.6 mol / L hexane solution) was added under a nitrogen atmosphere at -78°C and stirred at -78°C for 30 minutes. 0.22 g of 2-phenylcyclopropane-1-carboxaldehyde dissolved in 3 mL of tetrahydrofuran was then added and stirred at 0°C for 3 hours. 5 mL of 6 mol / L aqueous hydrochloric acid was then added and stirred at room temperature for 2 hours. Saturated aqueous sodium bicarbonate was then added and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.109 g of (2-phenylcyclopropyl)acetaldehyde (1:1). (3) To a solution of 0.108 g of (2-phenylcyclopropyl)acetaldehyde in 1 mL of ethanol, 0.031 g of sodium borohydride was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1 hour. Saturated aqueous ammonium chloride solution was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.106 g of 2-(2-phenylcyclopropyl)ethan-1-ol. (4) To a solution of 0.05 g of 2-(2-phenylcyclopropyl)ethan-1-ol in 2 mL of dichloromethane, 0.064 g of methanesulfonic anhydride and 0.107 mL of triethylamine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 0.074 g of crude 2-(2-phenylcyclopropyl)ethyl methanesulfonate. (5) To a solution of 0.06 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 2 mL of N,N-dimethylformamide, 0.011 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.069 g of crude 2-(2-phenylcyclopropyl)ethyl methanesulfonate was then added, and the mixture was stirred at room temperature for 19 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.046 g of (morpholin-4-yl)(1-(2-(2-phenylcyclopropyl)ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.49 (dd, J = 4.8, 1.2 Hz, 1H), 7.82 (s, 1H), 7.59 (dd, J = 8.0, 1.2 Hz, 1H), 7.21 (t, J = 7.6 Hz, 2H), 7.13 (t, J = 7.6 Hz, 1H), 7.05 (dd, J = 8.4, 4.8 Hz, 1H), 6.91 (d, J = 7.2 Hz, 2H), 4.27 (t, J = 6.8 Hz, 2H), 3.79 (s, 8H), 1.98-1.92 (m, 2H), 1.65-1.60 (m, 1H), 0.98-0.89 (m, 2H), 0.77-0.72 (m, 1H)

[0198] Example 29 1-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)-4-phenylbutan-2-one To a solution of 0.068 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.014 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.073 g of 1-bromo-4-phenylbutan-2-one was then added, and the mixture was stirred at room temperature for 18.5 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and then the solvent was distilled off under reduced pressure to obtain 0.021 g of 1-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)-4-phenylbutan-2-one. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.51 (m, 1H), 7.64 (s, 1H), 7.33-7.29 (m, 2H), 7.24-7.21 (m, 2H), 7.17-7.15 (m, 2H), 7.13-7.09 (m, 1H), 4.77 (s, 2H), 3.80 (s, 8H), 2.96 (t, J = 7.0 Hz, 2H), 2.81 (t, J = 7.2 Hz, 2H)

[0199] Example 30 (morpholin-4-yl)(1-((3-phenoxycyclobutyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.25 g of 3-((benzyloxy)methyl)cyclobutan-1-one in 3 mL of ethanol, 0.06 g of sodium borohydride was added at 0°C under a nitrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes. Saturated aqueous ammonium chloride solution was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.252 g of 3-((benzyloxy)methyl)cyclobutan-1-ol. (2) To a solution of 0.25 g of 3-((benzyloxy)methyl)cyclobutan-1-ol in 5 mL of toluene, 0.147 g of phenol, 0.409 g of triphenylphosphine, and 0.365 g of bis(2-methoxyethyl)azodicarboxylate were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at 70°C for 24 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=9:1), and the solvent was evaporated under reduced pressure to obtain 0.146 g of ((3-((benzyloxy)methyl)cyclobutyl)oxy)benzene. (3) To 0.146 g of ((3-((benzyloxy)methyl)cyclobutyl)oxy)benzene, 0.029 g of palladium-carbon was added under a nitrogen atmosphere, and then 4 mL of ethanol was added. The mixture was stirred at room temperature under a hydrogen atmosphere for 18 hours. After that, the mixture was filtered through Celite, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1). The solvent was then distilled off under reduced pressure to obtain 0.085 g of (3-phenoxycyclobutyl)methanol. (4) To a solution of 0.1 g of (3-phenoxycyclobutyl)methanol in 2 mL of dichloromethane, 0.223 g of carbon tetrabromide and 0.177 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 16 hours. The solvent was then removed by distillation under reduced pressure to obtain a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=4:1). The solvent was then removed by distillation under reduced pressure to obtain 0.105 g of ((3-(bromomethyl)cyclobutyl)oxy)benzene. (5) To a solution of 0.05 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.013 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.052 g of ((3-(bromomethyl)cyclobutyl)oxy)benzene and 0.018 g of potassium iodide were then added, and the mixture was stirred at room temperature for 18 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.022 g of (morpholin-4-yl)(1-((3-phenoxycyclobutyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.55 (dd, J = 4.8, 1.2 Hz, 1H), 7.87 (s, 1H), 7.70 (dd, J = 8.0, 1.2 Hz, 1H), 7.29-7.25 (m, 2H), 7.19 (dd, J = 8.0, 4.8 Hz, 1H), 6.95 (t, J = 7.6 Hz, 1H), 6.76 (d, J = 8.0 Hz, 2H), 4.80-4.77 (m, 1H), 4.26 (d, J = 8.0 Hz, 2H), 3.81 (s, 8H), 3.02-3.02 (m, 1H), 2.42-2.33 (m, 4H)

[0200] Example 31 (4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)(piperidin-1-yl)methanone (1) To a solution of 0.320 g of methyl 4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoate in 3 mL of tetrahydrofuran and 3 mL of water, 0.055 g of lithium hydroxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 24 hours. Then, a 5% aqueous solution of potassium hydrogen sulfate was added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (methanol:ethyl acetate=5:1), and the solvent was evaporated under reduced pressure to obtain 0.240 g of 4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid. (2) To a solution of 0.060 g of 4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid in 5 mL of N,N-dimethylformamide, 0.015 g of piperidine, 0.041 mL of N,N-diisopropylethylamine, and 0.067 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate=1:1), and the solvent was then distilled off under reduced pressure to obtain 0.050 g of (4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)(piperidin-1-yl)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.98-7.96 (m, 1H), 7.93 (s, 1H), 7.28-7.22 (m, 5H), 4.31 (t, J = 7.2 Hz, 2H), 3.72-3.72 (m, 10H), 3.36-3.36 (m, 2H), 2.68 (t, J = 7.6 Hz, 2H), 1.94-1.86 (m, 2H), 1.71-1.52 (m, 8H)

[0201] Example 32 N-Cyclohexyl-4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzamide To a solution of 0.060 g of 4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid in 1 mL of N,N-dimethylformamide, 0.024 g of cyclohexylamine hydrochloride, 0.041 mL of N,N-diisopropylethylamine, and 0.067 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using hexane:ethyl acetate=1:1. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate=1:1), and then the solvent was distilled off under reduced pressure to obtain 0.029 g of N-cyclohexyl-4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzamide. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.51 (m, 1H), 7.76 (s, 1H), 7.66-7.64 (m, 2H), 7.62-7.59 (m, 1H), 7.17-7.13 (m, 3H), 5.99-5.97 (m, 1H), 4.12 (t, J = 7.2 Hz, 2H), 4.02-3.92 (m, 1H), 3.80 (s, 8H), 2.68 (t, J = 7.2 Hz, 2H), 2.05-2.01 (m, 2H), 1.92-1.85 (m, 2H), 1.78-1.73 (m, 2H), 1.69-1.65 (m, 3H), 1.50-1.38 (m, 2H), 1.28-1.19 (m, 3H)

[0202] Example 33 N-Cyclohexyl-3-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzamide (1) 0.900 g of 2-propyn-1-ol, 0.031 g of copper(I) iodide, and 0.186 g of tetrakis(triphenylphosphine)palladium(0) were added to 30 mL of triethylamine and 4.21 g of 3-(methoxycarbonyl)-1-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50°C for 6 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 2.76 g of methyl 3-(3-hydroxyprop-1-yn-1-yl)benzoate. (2) 0.883 g of palladium-fibroin was added to 2.00 g of methyl 3-(3-hydroxyprop-1-yn-1-yl)benzoate under a nitrogen atmosphere, followed by 40 mL of methanol and stirring at room temperature for 42 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was removed under reduced pressure to obtain 1.99 g of methyl 3-(3-hydroxypropyl)benzoate. (3) To a solution of 1.99 g of methyl 3-(3-hydroxypropyl)benzoate in 20 mL of dichloromethane, 3.73 g of carbon tetrabromide and 2.95 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 44 hours. The solvent was then distilled off under reduced pressure to obtain a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then distilled off under reduced pressure to obtain 1.85 g of methyl 3-(3-bromopropyl)benzoate. (4) To a solution of 0.700 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 10 mL of N,N-dimethylformamide, 0.145 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.778 g of methyl 3-(3-bromopropyl)benzoate was then added, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and then the solvent was distilled off under reduced pressure to obtain 0.232 g of methyl 3-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoate. (5) To a solution of 0.232 g of methyl 3-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoate in a mixture of 3 mL of tetrahydrofuran and 3 mL of water, 0.041 g of lithium hydroxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 24 hours. Then, a 5% aqueous solution of potassium hydrogen sulfate was added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.210 g of 3-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoic acid. (6) To a solution of 0.060 g of 3-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoic acid in 1 mL of N,N-dimethylformamide, 0.025 g of cyclohexylamine hydrochloride, 0.043 mL of N,N-diisopropylethylamine, and 0.070 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate=1:5), and then the solvent was distilled off under reduced pressure to obtain 0.012 g of N-cyclohexyl-3-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzamide. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.52 (m, 1H), 7.76 (s, 1H), 7.60-7.55 (m, J = 5.0 Hz, 3H), 7.37-7.33 (m, 1H), 7.28 (s, 1H), 7.17-7.14 (m, 1H), 6.17-6.15 (m, 1H), 4.16 (t, J = 7.2 Hz, 2H), 4.02-3.93 (m, 1H), 3.80 (s, 8H), 2.67 (t, J = 7.6 Hz, 2H), 2.30-2.23 (m, 2H), 2.04-2.00 (m, 2H), 1.79-1.74 (m, 2H), 1.69-1.65 (m, 1H), 1.48-1.38 (m, 2H), 1.32-1.18 (m, 3H)

[0203] Example 34 Morpholino(1-(5-phenylpentyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.2 g of 5-phenyl-1-pentanol in 5 mL of dichloromethane, 0.348 g of p-toluenesulfonyl chloride and 0.338 mL of triethylamine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 18 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.123 g of 5-phenylpentyl 4-methylbenzene-1-sulfonate. (2) To a solution of 0.039 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.008 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.07 g of 5-phenylpentyl 4-methylbenzene-1-sulfonate was then added, and the mixture was stirred at room temperature for 1 hour. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=30:1), and then the solvent was distilled off under reduced pressure to obtain 0.007 g of morpholino(1-(5-phenylpentyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.52 (m, 1H), 7.81 (s, 1H), 7.65-7.62 (m, 1H), 7.28-7.25 (m, 2H), 7.20-7.12 (m, 4H), 4.12 (t, J = 7.4 Hz, 2H), 3.80 (s, 8H), 2.60 (t, J = 7.4 Hz, 2H), 1.94-1.86 (m, 2H), 1.70-1.62 (m, 2H), 1.42-1.34 (m, 2H)

[0204] Example 35 (1-(4-(4-(1-hydroxyethyl)phenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone To a solution of 0.080 g of 1-(4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)ethanone in 5 mL of ethanol, 0.009 g of sodium borohydride was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 17 hours. Then, saturated aqueous ammonium chloride solution was added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 0.060 g of (1-(4-(4-(1-hydroxyethyl)phenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.96-7.93 (m, 1H), 7.90 (s, 1H), 7.28-7.26 (m, 1H), 7.24-7.22 (m, 2H), 7.10-7.08 (m, 2H), 4.76 (q, J = 6.4 Hz, 1H), 4.28 (t, J = 7.2 Hz, 2H), 3.72 (s, 8H), 2.61 (t, J = 7.6 Hz, 2H), 1.91-1.84 (m, 2H), 1.65-1.57 (m, 2H), 1.40 (d, J = 6.4 Hz, 3H)

[0205] Example 36 (1-(4-(3-(1-hydroxyethyl)phenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone To a solution of 0.100 g of 1-(3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)ethanone in 5 mL of ethanol, 0.011 g of sodium borohydride was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 17 hours. Then, saturated aqueous ammonium chloride solution was added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 0.071 g of (1-(4-(3-(1-hydroxyethyl)phenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.95-7.93 (m, 1H), 7.90 (s, 1H), 7.28-7.22 (m, 3H), 7.10-7.08 (m, 2H), 4.76 (q, J = 6.4 Hz, 1H), 4.28 (t, J = 6.8 Hz, 2H), 3.71 (s, 8H), 2.61 (t, J = 7.2 Hz, 2H), 1.92-1.84 (m, 2H), 1.65-1.57 (m, 2H), 1.40 (d, J = 6.4Hz, 3H)

[0206] Example 37 (3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)(morpholino)methanone (1) To a solution of 0.442 g of methyl 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoate in 3 mL of tetrahydrofuran and 3 mL of water, 0.075 g of lithium hydroxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 1 hour. Then, a 5% aqueous solution of potassium hydrogen sulfate was added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (methanol:ethyl acetate=1:9), and the solvent was evaporated under reduced pressure to obtain 0.411 g of 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid. (2) To a solution of 0.05 g of 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid in 1 mL of N,N-dimethylformamide, 0.013 g of morpholine, 0.034 mL of N,N-diisopropylethylamine, and 0.055 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 4 hours. Thereafter, the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (methanol:ethyl acetate=1:9), and then the solvent was distilled off under reduced pressure to obtain 0.011 g of (3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53 (dd, J = 4.4, 1.2 Hz, 1H), 7.81 (s, 1H), 7.63 (dd, J = 8.4, 1.2 Hz, 1H), 7.31 (t, J = 8.0 Hz, 1H), 7.21-7.14 (m, 4H), 4.16-4.11 (m, 2H), 3.80-3.44 (m, 16H), 2.69-2.65 (m, 2H), 1.95-1.88 (m, 2H), 1.75-1.68 (m, 2H)

[0207] Example 38 (3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)(piperidin-1-yl)methanone To a solution of 0.053 g of 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid in 1 mL of N,N-dimethylformamide, 0.013 g of piperidine, 0.036 mL of N,N-diisopropylethylamine, and 0.059 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 4 hours. Thereafter, the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (methanol:ethyl acetate=1:9), and then the solvent was distilled off under reduced pressure to obtain 0.011 g of (3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)phenyl)(piperidin-1-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.52 (dd, J = 4.4, 1.2 Hz, 1H), 7.81 (s, 1H), 7.62 (dd, J = 8.4, 1.2 Hz, 1H), 7.29 (t, J = 7.6 Hz, 1H), 7.20-7.14 (m, 4H), 4.13 (t, J = 7.6 Hz, 2H), 3.80 (s, 8H), 3.70 (s, 2H), 3.31 (s, 2H), 2.66 (t, J = 7.6 Hz, 2H), 1.94-1.87 (m, 2H), 1.72-1.64 (m, 6H), 1.48 (s, 2H)

[0208] Example 39 N-Cyclohexyl-3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzamide To a solution of 0.053 g of 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoic acid in 1 mL of N,N-dimethylformamide, 0.021 g of cyclohexylamine hydrochloride, 0.037 mL of N,N-diisopropylethylamine, and 0.06 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 4 hours. Thereafter, the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (methanol:ethyl acetate=1:9), and then the solvent was distilled off under reduced pressure to obtain 0.030 g of N-cyclohexyl-3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzamide. obtained. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53-8.51 (m, 1H), 7.80 (s, 1H), 7.63-7.58 (m, 2H), 7.53-7.52 (m, 1H), 7.33-7.29 (m, 1H), 7.24-7.22 (m, 1H), 7.17-7.14 (m, 1H), 6.02-6.00 (m, 1H), 4.14 (t, J = 7.6 Hz, 2H), 4.01-3.93 (m, 1H), 3.80 (s, 8H), 2.66 (t, J = 7.6 Hz, 2H), 2.05-2.01 (m, 2H), 1.94-1.86 (m, 2H), 1.78-1.73 (m, 2H), 1.71-1.67 (m, 3H), 1.48-1.38 (m, 2H), 1.29-1.19 (m, 3H)

[0209] Example 40 N-Cyclohexyl-trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexanecarboxamide (1) To a solution of 0.5 g of methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate in 1 mL of dichloromethane, 1.155 g of carbon tetrabromide and 0.99 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 16 hours. The solvent was then removed by distillation under reduced pressure to obtain a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then removed by distillation under reduced pressure to obtain 0.574 g of methyl trans-4-(bromomethyl)cyclohexane-1-carboxylate. (2) To a solution of 0.434 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.09 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. Further, 0.574 g of methyl trans-4-(bromomethyl)cyclohexane-1-carboxylate and 0.156 g of potassium iodide were added, and the mixture was stirred at room temperature for 15 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and then the solvent was distilled off under reduced pressure to obtain 0.165 g of methyl trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexanecarboxylate. (3) To a solution of 0.154 g of methyl trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexanecarboxylate in 3 mL of tetrahydrofuran and 3 mL of water, 0.029 g of lithium hydroxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 1 hour. Then, 5% aqueous potassium hydrogen sulfate solution was added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 0.106 g of trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexanecarboxylic acid. (4) To a solution of 0.026 g of trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexanecarboxylic acid in 1 mL of N,N-dimethylformamide, 0.011 g of cyclohexylamine hydrochloride, 0.02 mL of N,N-diisopropylethylamine, and 0.032 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=5:1), and then the solvent was distilled off under reduced pressure to obtain 0.007 g of N-cyclohexyl-trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexanecarboxamide. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54-8.52 (m, 1H), 7.78 (s, 1H), 7.65-7.63 (m, 1H), 7.18-7.15 (m, 1H), 5.23 (d, J = 7.8 Hz, 1H), 3.98 (d, J = 6.8 Hz, 2H), 3.81-3.68 (m, 9H), 2.00-1.89 (m, 6H), 1.77-1.66 (m, 5H), 1.49-1.26 (m, 4H), 1.19-1.03 (m, 5H)

[0210] Example 41 (trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexyl)(piperidin-1-yl)methanone To a solution of 0.024 g of trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexanecarboxylic acid in 1 mL of N,N-dimethylformamide, 0.007 g of piperidine, 0.018 mL of N,N-diisopropylethylamine, and 0.029 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel chromatography (ethyl acetate:methanol=9:1), and then the solvent was distilled off under reduced pressure to obtain 0.027 g of (trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexyl)(piperidin-1-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54-8.52 (m, 1H), 7.78 (s, 1H), 7.66-7.64 (m, 1H), 7.19-7.15 (m, 1H), 4.00 (d, J = 6.8 Hz, 2H), 3.81 (s, 8H), 3.53 (t, J = 5.6 Hz, 2H), 3.40 (t, J = 5.0 Hz, 2H), 2.48-2.40 (m, 1H), 1.97-1.86 (m, 1H), 1.79-1.49 (m, 12H), 1.15-1.04 (m, 2H)

[0211] Example 42 (morpholin-4-yl)(1-(4-(oxan-4-yl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 1 g of benzyl 3-bromopropyl ether in 9 mL of acetonitrile, 1.145 g of triphenylphosphine was added at room temperature under a nitrogen atmosphere, and the mixture was stirred under reflux for 16 hours. After that, the solvent was distilled off under reduced pressure, and the residue was purified by recrystallization (hexane-diethyl ether). After that, the solvent was distilled off under reduced pressure to obtain 1.638 g of (3-(benzyloxy)propyl)triphenylphosphonium bromide. (2) To a solution of 0.5 g of (3-(benzyloxy)propyl)triphenylphosphonium bromide in 4 mL of tetrahydrofuran, 2.015 mL of potassium bis(trimethylsilyl)amide (0.5 mol / L toluene solution) was added under a nitrogen atmosphere at −20°C, and the mixture was stirred at −20°C for 5 minutes. Further, 0.139 g of tetrahydro-2H-pyran-4-carboxaldehyde was added, and the mixture was stirred at −78°C for 2 hours. Saturated aqueous ammonium chloride solution was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.125 g of 4-(4-(benzyloxy)but-1-en-1-yl)oxane. (3) To 0.125 g of 4-(4-(benzyloxy)but-1-en-1-yl)oxane, 0.027 g of palladium-carbon was added under a nitrogen atmosphere, followed by the addition of 2 mL of ethanol, and the mixture was stirred at room temperature for 22 hours under a hydrogen atmosphere. The mixture was then filtered through Celite, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then distilled off under reduced pressure to obtain 0.06 g of 4-(oxan-4-yl)butan-1-ol. (4) To a solution of 0.06 g of 4-(oxan-4-yl)butan-1-ol in 1 mL of dichloromethane, 0.151 g of carbon tetrabromide and 0.129 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. The crude product obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was then distilled off under reduced pressure to give 0.084 g of 4-(4-bromobutyl)oxane. (5) To a solution of 0.06 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.037 g of sodium tert-butoxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 15 minutes. 0.063 g of 4-(4-bromobutyl)oxane and 0.022 g of potassium iodide were then added, and the mixture was stirred at room temperature for 3 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=9:1), and the solvent was evaporated under reduced pressure to obtain 0.026 g of (morpholin-4-yl)(1-(4-(oxan-4-yl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53 (dd, J = 4.8, 1.2 Hz, 1H), 7.83 (s, 1H), 7.66 (dd, J = 8.4, 1.2 Hz, 1H), 7.17 (dd, J = 8.4, 4.8 Hz, 1H), 4.14 (t, J = 7.2 Hz, 2H), 3.93 (dd, J = 11.2, 3.6 Hz, 2H), 3.80 (s, 8H), 3.34 (t, J = 11.6 Hz, 2H), 1.91-1.84 (m, 2H), 1.54 (d, J = 14.2 Hz, 2H), 1.47-1.40 (m, 1H), 1.38-1.32 (m, 2H), 1.30-1.18 (m, 4H)

[0212] Example 43 (4-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)phenyl)(piperidin-1-yl)methanone (1) 1.14 g of 2-propyn-1-ol, 0.039 g of copper(I) iodide, and 0.234 g of tetrakis(triphenylphosphine)palladium(0) were added to 30 mL of triethylamine and 5.31 g of 4-(methoxycarbonyl)-1-iodobenzene at room temperature under a nitrogen atmosphere and stirred at 50°C for 4 hours. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to obtain 3.60 g of methyl 4-(3-hydroxyprop-1-yn-1-yl)benzoate. (2) 0.883 g of palladium-fibroin was added to 2.00 g of methyl 4-(3-hydroxyprop-1-yn-1-yl)benzoate under a nitrogen atmosphere, followed by 40 mL of methanol and stirring at room temperature for 48 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then distilled off under reduced pressure to obtain 1.80 g of methyl 4-(3-hydroxypropyl)benzoate. (3) To a solution of 1.80 g of methyl 4-(3-hydroxypropyl)benzoate in 20 mL of dichloromethane, 3.38 g of carbon tetrabromide and 2.67 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 21 hours. The solvent was then removed by distillation under reduced pressure to obtain a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then removed by distillation under reduced pressure to obtain 2.10 g of methyl 4-(3-bromopropyl)benzoate. (4) To a solution of 0.250 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 2 mL of N,N-dimethylformamide, 0.126 g of sodium tert-butoxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.364 g of methyl 4-(3-bromopropyl)benzoate was then added, and the mixture was stirred at room temperature for 1 hour. The solvent was then distilled off under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (methanol:ethyl acetate=1:9), and the solvent was then distilled off under reduced pressure to obtain 0.321 g of methyl 4-(3-(3-(morpholin-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoate. (5) To a mixed solution of 0.321 g of methyl 4-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoate in 2 mL of tetrahydrofuran and 2 mL of water, 0.057 g of lithium hydroxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 1 hour. The solvent was then distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel chromatography (methanol:ethyl acetate=1:9), and the solvent was then distilled off under reduced pressure to obtain 0.223 g of 4-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoic acid. (6) To a solution of 0.049 g of 4-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoic acid in 1 mL of N,N-dimethylformamide, 0.014 g of piperidine, 0.038 mL of N,N-diisopropylethylamine, and 0.061 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 24 hours. Thereafter, the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (methanol:ethyl acetate=1:9), and then the solvent was distilled off under reduced pressure to obtain 0.056 g of (4-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)phenyl)(piperidin-1-yl)methanone. 1H-NMR (400 MHz, METHANOL-D4) δ 8.43-8.42 (m, 1H), 7.94-7.90 (m, 2H), 7.28-7.23 (m, 5H), 4.30 (t, J = 7.6 Hz, 2H), 3.71-3.67 (m, 12H), 2.67 (t, J = 7.6 Hz, 2H), 2.24-2.16 (m, 2H), 1.68-1.63 (m, 4H), 1.50 (s, 2H)

[0213] Example 44 N-Cyclohexyl-4-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzamide To a solution of 0.043 g of 4-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoic acid in 1 mL of N,N-dimethylformamide, 0.019 g of cyclohexylamine hydrochloride, 0.033 mL of N,N-diisopropylethylamine, and 0.053 g of 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 24 hours. Thereafter, the solvent was distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (methanol:ethyl acetate = 1:9), and then the solvent was distilled off under reduced pressure to obtain 0.014 g of N-cyclohexyl-4-(3-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzamide. 1H-NMR (400 MHz, METHANOL-D4) δ 8.41-8.40 (m, 1H), 7.92-7.90 (m, 2H), 7.67-7.65 (m, 2H), 7.27-7.21 (m, 3H), 4.29 (t, J = 7.6 Hz, 2H), 3.85-3.57 (m, 9H), 2.68 (t, J = 7.6 Hz, 2H), 2.24-2.17 (m, 2H), 1.92-1.87 (m, 2H), 1.79-1.76 (m, 2H), 1.67-1.64 (m, 1H), 1.39-1.27 (m, 5H)

[0214] Example 45 (1-(4-(3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) To a solution of 0.500 g of 3-bromobenzoylhydrazine in 5 mL of toluene, 0.371 g of triethyl orthoacetate and 0.061 g of ammonium chloride were added under a nitrogen atmosphere at 0°C, and the mixture was stirred under reflux for 6 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.483 g of 2-(3-bromophenyl)-5-methyl-1,3,4-oxadiazole. (2) 0.483 g of 2-(3-bromophenyl)-5-methyl-1,3,4-oxadiazole, 0.077 g of copper(I) iodide, 0.233 g of tetrakis(triphenylphosphine)palladium(0), and 5 mL of acetonitrile were added to 1.4 mL of triethylamine and 0.212 g of 3-butyn-1-ol at room temperature under a nitrogen atmosphere. The mixture was then filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.383 g of 4-(3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)but-3-yn-1-ol. (3) To 0.383 g of 4-(3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)but-3-yn-1-ol, 0.004 g of palladium-carbon was added under a nitrogen atmosphere, followed by the addition of 5 mL of ethanol. The mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. After filtration through Celite, 0.311 g of crude 4-(3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)butan-1-ol was obtained. To a solution of 0.311 g of crude 4-(3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)butan-1-ol in 3 mL of dichloromethane, 0.532 g of carbon tetrabromide and 0.456 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 24 hours. The crude product obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was then distilled off under reduced pressure to obtain 0.292 g of 2-(3-(4-bromobutyl)phenyl)-5-methyl-1,3,4-oxadiazole. (4) To a solution of 0.032 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.016 g of sodium tert-butoxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.053 g of 2-(3-(4-bromobutyl)phenyl)-5-methyl-1,3,4-oxadiazole was added, and the mixture was stirred at room temperature for 1 hour. Water was then added, and the mixture was separated using hexane:ethyl acetate = 1:1. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (methanol:ethyl acetate=1:9), and then the solvent was distilled off under reduced pressure to obtain 0.025 g of (1-(4-(3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)butyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.50 (dd, J = 4.4, 1.2 Hz, 1H), 7.83-7.79 (m, 3H), 7.60 (dd, J = 8.4, 1.2 Hz, 1H), 7.41-7.37 (m, 1H), 7.27 (d, J = 7.6 Hz, 1H), 7.15-7.11 (m, 1H), 4.13 (t, J = 7.6 Hz, 2H), 3.78 (s, 8H), 2.71 (t, J = 7.6 Hz, 2H), 2.61 (s, 3H), 1.93-1.87 (m, 2H), 1.75-1.67 (m, 2H)

[0215] Example 46 Morpholino(1-((cis-4-phenoxycyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) 5.2 mL of an ethanol-concentrated sulfuric acid mixed solution was added to 0.5 g of trans-4-hydroxycyclohexane-1-carboxylic acid at room temperature under a nitrogen atmosphere, and the mixture was stirred under reflux for 19 hours. Saturated aqueous sodium bicarbonate was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was removed under reduced pressure to obtain 0.538 g of ethyl trans-4-hydroxycyclohexane-1-carboxylate. (2) To a solution of 0.2 g of ethyl trans-4-hydroxycyclohexane-1-carboxylate in 3 mL of toluene, 0.131 g of phenol, 0.366 g of triphenylphosphine, and 0.326 g of bis(2-methoxyethyl) azodicarboxylate were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 22 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:4), and the solvent was evaporated under reduced pressure to obtain 0.125 g of ethyl cis-4-phenoxycyclohexane-1-carboxylate. (3) To a solution of 0.12 g of ethyl cis-4-phenoxycyclohexane-1-carboxylate in 1 mL of toluene, 0.268 mL of sodium bis(2-methoxyethoxy)aluminum hydride (70% toluene solution, approximately 3.6 mol / L) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 2 hours. A saturated aqueous solution of potassium sodium tartrate was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.08 g of (cis-4-phenoxycyclohexyl)methanol. (4) To a solution of 0.077 g of (cis-4-phenoxycyclohexyl)methanol in 1 mL of dichloromethane, 0.149 g of carbon tetrabromide and 0.127 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 2 hours. The solvent was then removed by distillation under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=1:4). The solvent was then removed by distillation under reduced pressure to obtain 0.095 g of ((cis-4-(bromomethyl)cyclohexyl)oxy)benzene. (5) To a solution of 0.055 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.049 g of potassium carbonate, 0.064 g of ((cis-4-(bromomethyl)cyclohexyl)oxy)benzene, and 0.02 g of potassium iodide were added at room temperature under a nitrogen atmosphere, and the mixture was stirred at 90°C for 20 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was then distilled off under reduced pressure to obtain 0.004 g of morpholino(1-((cis-4-phenoxycyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54 (dd, J = 4.8, 1.2 Hz, 1H), 7.82 (s, 1H), 7.69 (dd, J = 8.4, 1.2 Hz, 1H), 7.31-7.28 (m, 2H), 7.18 (dd, J = 8.4, 4.8 Hz, 1H), 6.97-6.91 (m, 3H), 4.56-4.56 (m, 1H), 4.04 (d, J = 7.2 Hz, 2H), 3.82 (s, 8H), 2.09-2.07 (m, 2H), 1.60-1.46 (m, 7H)

[0216] Example 47 Morpholino(1-((trans-4-phenoxycyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.2 g of ethyl cis-4-hydroxycyclohexane-1-carboxylate in 3 mL of toluene, 0.131 g of phenol, 0.366 g of triphenylphosphine, and 0.326 g of bis(2-methoxyethyl) azodicarboxylate were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 22 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.126 g of ethyl trans-4-phenoxycyclohexane-1-carboxylate. (2) To a solution of 0.12 g of ethyl trans-4-phenoxycyclohexane-1-carboxylate in 1 mL of toluene, 0.268 mL of sodium bis(2-methoxyethoxy)aluminum hydride (70% toluene solution, approximately 3.6 mol / L) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. Saturated aqueous potassium sodium tartrate was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to obtain 0.077 g of (trans-4-phenoxycyclohexyl)methanol. (3) To a solution of 0.08 g of (trans-4-phenoxycyclohexyl)methanol in 1 mL of dichloromethane, 0.154 g of carbon tetrabromide and 0.132 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 2 hours. The crude product obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=9:1), and the solvent was then distilled off under reduced pressure. As a result, 0.096 g of ((trans-4-(bromomethyl)cyclohexyl)oxy)benzene was obtained. (4) To a solution of 0.055 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.049 g of potassium carbonate, 0.064 g of ((trans-4-(bromomethyl)cyclohexyl)oxy)benzene, and 0.02 g of potassium iodide were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at 90°C for 20 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to obtain 0.005 g of morpholino(1-((trans-4-phenoxycyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.53 (dd, J = 4.8, 1.2 Hz, 1H), 7.80 (s, 1H), 7.65 (dd, J = 8.0, 1.2 Hz, 1H), 7.27-7.23 (m, 2H), 7.17 (dd, J = 8.0, 4.8 Hz, 1H), 6.92 (t, J = 7.2 Hz, 1H), 6.86 (d, J = 8.0 Hz, 2H), 4.17-4.12 (m, 1H), 4.01 (d, J = 6.8 Hz, 2H), 3.81 (s, 8H), 2.19-2.17 (m, 2H), 1.93-1.91 (m, 1H), 1.79-1.76 (m, 2H), 1.45-1.35 (m, 2H), 1.24-1.17 (m, 2H)

[0217] Example 48 (1-((4-hydroxy-4-phenylcyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) To a solution of 0.5 g of 4-(hydroxymethyl)cyclohexanone in 5 mL of pyridine, 0.892 g of p-toluenesulfonyl chloride was added at 0°C under a nitrogen atmosphere and stirred at room temperature for 26 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.849 g of (4-oxocyclohexyl)methyl 4-methylbenzene-1-sulfonate. (2) To a solution of 0.535 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.48 g of potassium carbonate was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 10 minutes. 0.954 g of (4-oxocyclohexyl)methyl 4-methylbenzene-1-sulfonate was then added, and the mixture was stirred at room temperature for 21 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by silica gel chromatography (ethyl acetate:methanol=9:1), and then the solvent was distilled off under reduced pressure to obtain 0.435 g of 4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexan-1-one. (3) To a solution of 0.05 g of 4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexan-1-one in 3 mL of tetrahydrofuran, 0.19 mL of phenylmagnesium bromide (1.0 mol / L tetrahydrofuran solution) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 20 hours. Saturated aqueous ammonium chloride solution was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a crude product. The crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=9:1), and the solvent was evaporated under reduced pressure to give 0.019 g of (1-((4-hydroxy-4-phenylcyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (dr 1:0.7). 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54-8.52 (m, 1.7H), 7.84 (s, 1H), 7.77 (s, 0.7H), 7.71-7.69 (m, 1H), 7.63-7.61 (m, 0.7H), 7.55-7.52 (m, 1.4H), 7.47-7.43 (m, 2.4H), 7.42-7.40 (m, 1H), 7.36-7.31 (m, 2.7H), 7.27-7.23 (m, 1H), 7.19-7.14 (m, 1.7H), 4.07 (d, J = 7.6 Hz, 2H), 4.00 (d, J = 7.2 Hz, 1.4H), 3.81 (s, 13.6H), 2.42-2.37 (m, 1.7H), 2.19-2.08 (m, 0.7H), 2.02-1.90 (m, 1H), 1.87-1.57 (m, 10.9H), 1.49 (s, 1H), 1.27-1.14 (m, 1.7H)

[0218] Example 49 (1-((trans-4-benzoylcyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) To a solution of 1 g of methyl trans-4-(hydroxymethyl)cyclohexanecarboxylate in 3 mL of N,N-dimethylformamide was added 0.791 g of imidazole at room temperature under a nitrogen atmosphere and stirred for 30 minutes. 0.963 g of tert-butyldimethylchlorosilane was then added and stirred at room temperature for 20 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane and ethyl acetate = 4:1), and the solvent was removed under reduced pressure to obtain 1.215 g of methyl trans-4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexanecarboxylate. (2) To a solution of 3.204 g of methyl trans-4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexanecarboxylate in 3 mL of tetrahydrofuran and 3 mL of water, 0.804 g of lithium hydroxide was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 20.5 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (ethyl acetate:methanol=9:1), and the solvent was evaporated under reduced pressure to obtain 2.55 g of trans-4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexanecarboxylic acid. (3) To a solution of 2.55 g of trans-4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexanecarboxylic acid in 3 mL of N,N-dimethylformamide, 1.096 g of N,O-dimethylhydroxylamine hydrochloride, 4.602 mL of N,N-diisopropylethylamine, 1.518 g of 1-hydroxybenzotriazole monohydrate, and 2.153 g of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 25 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then distilled off under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and then the solvent was distilled off under reduced pressure to obtain 2.236 g of trans-4-(((tert-butyldimethylsilyl)oxy)methyl)-N-methoxy-N-methylcyclohexanecarboxamide. (4) To a solution of 1 g of trans-4-(((tert-butyldimethylsilyl)oxy)methyl)-N-methoxy-N-methylcyclohexanecarboxamide in 5 mL of tetrahydrofuran, 9.508 mL of phenylmagnesium bromide (1.0 mol / L tetrahydrofuran solution) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 48 hours. Saturated aqueous ammonium chloride solution was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.987 g of (trans-4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexyl)(phenyl)methanone. (5) To a solution of 1.099 g of (trans-4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexyl)(phenyl)methanone in 3 mL of tetrahydrofuran, 1.296 mL of tetrabutylammonium fluoride (approximately 1 mol / L tetrahydrofuran solution) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 20 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.609 g of (trans-4-(hydroxymethyl)cyclohexyl)(phenyl)methanone. (6) To a solution of 0.609 g of (trans-4-(hydroxymethyl)cyclohexyl)(phenyl)methanone in 1 mL of dichloromethane, 1.11 g of carbon tetrabromide and 0.951 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 2 hours. The solvent was then removed by distillation under reduced pressure to obtain a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then removed by distillation under reduced pressure to obtain 0.68 g of (trans-4-(bromomethyl)cyclohexyl)(phenyl)methanone. (7) To a solution of 0.43 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.385 g of potassium carbonate was added at room temperature under a nitrogen atmosphere and stirred at room temperature for 30 minutes. 0.68 g of (trans-4-(bromomethyl)cyclohexyl)(phenyl)methanone was added and stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=9:1), and the solvent was then distilled off under reduced pressure to obtain 0.175 g of (1-((trans-4-benzoylcyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54-8.53 (m, 1H), 7.93-7.91 (m, 2H), 7.81 (s, 1H), 7.68-7.65 (m, 1H), 7.58-7.54 (m, 1H), 7.48-7.44 (m, 2H), 7.19-7.16 (m, 1H), 4.04 (d, J = 6.8 Hz, 2H), 3.81 (s, 8H), 3.28-3.20 (m, 1H), 1.99-1.89 (m, 3H), 1.84-1.80 (m, 2H), 1.56-1.46 (m, 2H), 1.28-1.17 (m, 2H)

[0219] Example 50 (1-((4-(hydroxy(phenyl)methyl)cyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone To a solution of 0.173 g of (1-((trans-4-benzoylcyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone in 2 mL of tetrahydrofuran and 1 mL of water, 0.023 g of sodium borohydride was added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=5:1), and the solvent was evaporated under reduced pressure to obtain 0.093 g of (1-((4-(hydroxy(phenyl)methyl)cyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (dr 1:0.1). 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.52-8.50 (m, 1.1H), 7.80 (s, 0.1H), 7.76 (s, 1H), 7.64-7.60 (m, 1.1H), 7.39-7.31 (m, 2.2H), 7.27-7.24 (m, 3.3H), 7.17-7.12 (m, 1.1H), 4.59-4.58 (m, 0.1H), 4.37-4.35 (m, 1H), 4.10-4.07 (m, 0.2H), 3.94 (d, J = 6.8 Hz, 2H), 3.79 (s, 8H), 3.76 (s, 0.8H), 2.63 (s, 0.1H), 2.16 (s, 1H), 2.08-2.02 (m, 1.1H), 1.90-1.69 (m, 3.3H), 1.62-1.62 (m, 1.1H), 1.44-1.42 (m, 1.1H), 1.26-1.26 (m, 1.1H), 1.10-0.90 (m, 3.3H)

[0220] Example 51 N-(trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexyl)benzamide (1) To a solution of 2 g of trans-4-aminocyclohexylmethanol in 15 mL of dichloromethane, 8.583 mL of triethylamine, 8.446 g of di-tert-butyl dicarbonate, and 0.095 g of 4-dimethylaminopyridine were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 5 hours. Water was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 1.578 g of tert-butyl (trans-4-(((tert-butoxycarbonyl)oxy)methyl)cyclohexyl)carbamate. (2) To a solution of 1.57 g of tert-butyl (trans-4-(((tert-butoxycarbonyl)oxy)methyl)cyclohexyl)carbamate in 10 mL of methanol was added 0.267 g of potassium hydroxide at room temperature under a nitrogen atmosphere, and the mixture was stirred at room temperature for 18 hours. Then, a 3 mol / L aqueous hydrochloric acid solution was added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.645 g of tert-butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate. (3) To a solution of 0.7 g of tert-butyl (trans-4-(hydroxymethyl)cyclohexyl)carbamate in 10 mL of dichloromethane, 1.215 g of carbon tetrabromide and 1.041 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 2 hours. The solvent was then distilled off under reduced pressure to obtain a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=4:1). The solvent was then distilled off under reduced pressure to obtain 0.437 g of tert-butyl (trans-4-(bromomethyl)cyclohexyl)carbamate. (4) To a solution of 0.25 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 3 mL of N,N-dimethylformamide, 0.146 g of sodium tert-butoxide, 0.316 g of tert-butyl (trans-4-(bromomethyl)cyclohexyl)carbamate, and 0.09 g of potassium iodide were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 19 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel chromatography (ethyl acetate:methanol=9:1), and then the solvent was distilled off under reduced pressure to obtain 0.163 g of tert-butyl (trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexyl)carbamate. (5) To a solution of 0.18 g of tert-butyl (trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexyl)carbamate in 2 mL of ethyl acetate, 2.119 mL of hydrogen chloride-ethyl acetate solution (approximately 4 mol / L) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 3 hours. The solvent was then removed under reduced pressure, and the residue was triturated with diethyl ether and filtered to obtain 0.075 g of (1-((trans-4-aminocyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone hydrochloride. (6) To a solution of 0.03 g of (1-((trans-4-aminocyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone hydrochloride in 1 mL of N,N-dimethylformamide, 0.111 mL of triethylamine and 0.019 mL of benzoyl chloride were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=9:1), and the solvent was evaporated under reduced pressure to obtain 0.011 g of N-(trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexyl)benzamide. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.56 (dd, J = 4.8, 1.2 Hz, 1H), 7.83 (s, 1H), 7.76-7.74 (m, 2H), 7.68 (dd, J = 8.4, 1.2 Hz, 1H), 7.53-7.49 (m, 1H), 7.46-7.42 (m, 2H), 7.20 (dd, J = 8.4, 4.8 Hz, 1H), 5.92 (d, J = 7.6 Hz, 1H), 4.03 (d, J = 7.6 Hz, 2H), 4.00-3.97 (m, 1H), 3.83 (s, 8H), 2.20-2.15 (m, 2H), 1.89-1.89 (m, 1H), 1.80-1.76 (m, 2H), 1.31-1.19 (m, 4H)

[0221] Example 52 N-(trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexyl)cyclohexanecarboxamide To a solution of 0.03 g of (1-((trans-4-aminocyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone hydrochloride in 1 mL of N,N-dimethylformamide, 0.111 mL of triethylamine and 0.022 mL of cyclohexanecarbonyl chloride were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=9:1), and the solvent was evaporated under reduced pressure to obtain 0.017 g of N-(trans-4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexyl)cyclohexanecarboxamide. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.55 (d, J = 4.4 Hz, 1H), 7.81 (s, 1H), 7.67 (dd, J = 8.4, 1.2 Hz, 1H), 7.20 (dd, J = 8.4, 4.4 Hz, 1H), 5.27 (s, 1H), 4.00 (d, J = 6.8 Hz, 2H), 3.81 (s, 8H), 3.78-3.74 (m, 1H), 2.05-2.00 (m, 3H), 1.86-1.78 (m, 5H), 1.74-1.70 (m, 3H), 1.47-1.38 (m, 2H), 1.28-1.17 (m, 5H), 1.12-1.05 (m, 2H)

[0222] Example 53 (1-((1,1'-bi(cyclohexane))-4-ylmethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) To a solution of 2 g of 4-cyclohexylcyclohexanol in 10 mL of dichloromethane, 4.886 g of Dess-Martin periodinane was added at 0°C under a nitrogen atmosphere and stirred at room temperature for 5 hours. Saturated aqueous sodium thiosulfate was then added, and the mixture was separated using dichloromethane. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 1.634 g of (1,1'-bi(cyclohexane))-4-one. (2) To a solution of 1.046 g of (methoxymethyl)triphenylphosphonium chloride in 9 mL of tetrahydrofuran, 1.907 mL of n-butyllithium (1.6 mol / L hexane solution) was added under a nitrogen atmosphere at -78°C, and the mixture was stirred at -78°C for 30 minutes. Further, 0.5 g of (1,1'-bi(cyclohexane))-4-one dissolved in 3 mL of tetrahydrofuran was added, and the mixture was stirred at 0°C for 4 hours. Then, 3 mL of 6 mol / L aqueous hydrochloric acid was added, and the mixture was stirred at room temperature for 17 hours. Then, saturated aqueous sodium bicarbonate solution was added, and the mixture was separated with ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain a crude product. The obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and then the solvent was distilled off under reduced pressure to obtain 0.245 g (dr 1:0.3) of (1,1'-bi(cyclohexane))-4-carboxaldehyde. (3) To a solution of 0.4 g of (1,1'-bi(cyclohexane))-4-carboxaldehyde in 4 mL of ethanol, 0.093 g of sodium borohydride was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1.5 hours. Saturated aqueous ammonium chloride solution was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.356 g of ((1,1'-bi(cyclohexane))-4-yl)methanol (dr 1:0.3). (4) To a solution of 0.36 g of ((1,1'-bi(cyclohexane))-4-yl)methanol in 4 mL of dichloromethane, 0.73 g of carbon tetrabromide and 0.529 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 21 hours. The solvent was then removed by distillation under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate = 9:1). The solvent was then removed by distillation under reduced pressure to obtain 0.475 g of 4-(bromomethyl)-1,1'-bi(cyclohexane) (dr 1:0.3). (5) To a solution of 0.07 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.041 g of sodium tert-butoxide, 0.082 g of 4-(bromomethyl)-1,1'-bi(cyclohexane), and 0.025 g of potassium iodide were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to give 0.016 g (dr 1:0.1) of (1-((1,1'-bi(cyclohexane))-4-ylmethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.52-8.51 (m, 1.1H), 7.81 (s, 0.1H), 7.79 (s, 1H), 7.66-7.63 (m, 1.1H), 7.17-7.13 (m, 1.1H), 4.07 (d, J = 8.0 Hz, 0.2H), 3.95 (d, J = 6.8 Hz, 2H), 3.81 (s, 8.8H), 1.79-1.64 (m, 9.5H), 1.49-1.45 (m, 0.8H), 1.32-1.41 (m, 0.2H), 1.23-1.10 (m, 3.6H), 1.07-0.92 (m, 9H)

[0223] Example 54 (1-(2-((1,1'-bi(cyclohexane))-4-yl)ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone (1) To a solution of 0.622 g of ethyl diethylphosphonoacetate in 7 mL of tetrahydrofuran, 0.122 g of sodium hydride (60%, dispersed in liquid paraffin) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at 0°C for 30 minutes. 0.5 g of (1,1'-bi(cyclohexane))-4-one was then added, and the mixture was stirred at room temperature for 24 hours. Saturated aqueous ammonium chloride solution was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 0.385 g of ethyl ((1,1'-bi(cyclohexane))-4-ylidene)acetate. (2) 0.38 g of ethyl ((1,1'-bi(cyclohexane))-4-ylidene)acetate was added to 0.213 g of palladium-fibroin under a nitrogen atmosphere, followed by 4 mL of ethyl acetate. The mixture was stirred at room temperature under a hydrogen atmosphere for 24 hours. The crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 4:1). The solvent was then removed under reduced pressure to obtain 0.331 g of ethyl ((1,1'-bi(cyclohexane))-4-yl)acetate (dry 1:0:5). (3) To a solution of 0.35 g of ethyl ((1,1'-bi(cyclohexane))-4-yl)acetate in 3 mL of toluene, 0.77 mL of sodium bis(2-methoxyethoxy)aluminum hydride (70% toluene solution, approximately 3.6 mol / L) was added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1.5 hours. A saturated aqueous solution of potassium sodium tartrate was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain a crude product. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to obtain 0.292 g of 2-((1,1'-bi(cyclohexane))-4-yl)ethan-1-ol. (4) To a solution of 0.36 g of 2-((1,1'-bi(cyclohexane))-4-yl)ethan-1-ol in 4 mL of dichloromethane, 0.681 g of carbon tetrabromide and 0.494 g of triphenylphosphine were added under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 24 hours. The crude product obtained by distilling off the solvent under reduced pressure was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was then distilled off under reduced pressure to obtain 0.468 g of 4-(2-bromomethyl)-1,1'-bi(cyclohexane). (5) To a solution of 0.07 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone in 1 mL of N,N-dimethylformamide, 0.041 g of sodium tert-butoxide, 0.087 g of 4-(2-bromomethyl)-1,1'-bi(cyclohexane), and 0.025 g of potassium iodide were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using a 1:1 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain the crude product. The obtained crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to give 0.041 g (dr 1:0.7) of (1-(2-((1,1'-bi(cyclohexane))-4-yl)ethyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.55-8.54 (m, 1.7H), 7.86 (s, 0.7H), 7.85 (s, 1H), 7.69-7.66 (m, 1.7H), 7.20-7.16 (m, 1.7H), 4.19-4.13 (m, 3.4H), 3.83 (s, 13.6H), 1.90-1.67 (m, 16.1H), 1.54-1.39 (m, 5.4H), 1.26-0.92 (m, 17.6H)

[0224] Example 55 Morpholino(6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) To a solution of 0.700 g of 6-bromo-1H-pyrrolo[3,2-b]pyridine-3-carboxaldehyde in 10 mL of N,N-dimethylformamide, 0.149 g of sodium hydride (60%, dispersed in liquid paraffin) was added at 0°C under a nitrogen atmosphere and stirred at room temperature for 40 minutes. A solution of 0.862 g of 4-phenylbutyl bromide in 10 mL of N,N-dimethylformamide was then slowly added dropwise at 0°C, followed by the addition of 0.258 g of potassium iodide, and the mixture was stirred at room temperature for 24 hours. Water was then added, and the mixture was separated using a 1:4 mixture of hexane and ethyl acetate. The resulting organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to obtain the crude product. The obtained crude product was purified by silica gel chromatography (hexane:ethyl acetate=7:3), and then the solvent was distilled off under reduced pressure to obtain 0.965 g of 6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxaldehyde. (2) To a mixture of 0.965 g of 6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxaldehyde, 21 mL of tert-butanol, 7 mL of tetrahydrofuran, and 3.5 mL of 2-methyl-2-b...

Claims

1. Formula (I): 【Chemistry 1】 [In the formula, R １ and R ２ are taken together with the nitrogen atom to which they are attached to form the following formulae (IIa) to (IIe): 【Chemistry 2】 (In the formula, Rx and Ry each independently represent an oxo group, an optionally substituted aryloxy group, or an optionally substituted C １－６ an alkyl group, wherein two Rx and two Ry may each independently be joined together with the carbon atom to which they are attached to form a heterocycloalkane or a cycloalkane; Rz is a hydrogen atom or an optionally substituted C １－６ represents an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R １ and R ２ are each independently C １－６ C optionally substituted with an alkoxy group １－６ represents an alkyl group; f R ３ are each independently C １－６ Alkyl group, C ２－６ Alkenyl group, —COR ｇ (R ｇ is C １－６ alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR ａ１ R ｂ１ (R ａ１ and R ｂ１ is as described below), -OR ｃ１ (R ｃ１ represents a halogen atom; f represents an integer of 0 to 3; R ３ａ is a hydrogen atom, C １－６ Alkyl group, C ２－６ Alkenyl group, —COR ｇ (R ｇ is C １－６ alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR ａ１ R ｂ１ (R ａ１ and R ｂ１ is as described below), -OR ｃ１ (R ｃ１ represents a halogen atom; A represents an optionally substituted divalent hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; g represents 0 or 1; Q is C １－６ represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group is the same or different and has 1 to 3 R ４ (where R ４ each independently represents an optionally substituted C １－６ an alkyl group, an optionally substituted aromatic heterocyclic group, a nitro group, —NR ａ２ R ｂ２ (R ａ２ and R ｂ２ is as described below), -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ R ｃ３ (R ｃ３ is as described below), -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ is as defined below, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or —COR ｅ (R ｅ is an optionally substituted C １－６ (Alkyl group) optionally substituted with; M １ is C １－６ Alkyl group or C ６－１４ C optionally substituted with an aryl group １－４ represents an alkylene group; M ２ is -(CH ２ ) ｊ１ -, -(CH ２ ) ｊ２ -O-(CH ２ ) ｊ３ --, --CONR ａ４ -, -NR ａ５ CO-, -(CH ２ ) ｊ４ -CO-(CH ２ ) ｊ５ -, -(CH ２ ) ｊ６ -CH(R)-(CH ２ ) ｊ７ -, -(CH ２ ) ｊ８ -S-(CH ２ ) ｊ９ - or -NR ａ６ - (wherein, R ａ４ ~R ａ６ is as described below, and j1 to j9 each independently represent an integer of 0 to 4; R represents a hydroxyl group or an aryl group; R ａ１ ~R ａ６ , and R ｂ１ ~R ｂ３ are each independently a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ２－８ an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or —COR f (R f is C １－６ an alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group; R ｃ１ ~R ｃ３ are each independently a hydrogen atom, an optionally substituted C １－６ Alkyl group, -COR ｈ (R h is C １－６ alkyl group), or an optionally substituted aryl group. however, (1) M １ Ga-(CH ２ )-, g is 0, and M ２ Ga-(CH ２ ) ｊ１ -, and when j1 is 0 and Q is benzene, R ４ is not a pyrazolyl group substituted with a methyl group. (2) M １ Ga-(CH ２ )-, g is 1, A is benzene, and M ２ But -(CH ２ ) ｊ１ -, and when j1 is 0 and Q is pyrazole, R ４ is not a methyl group. or a pharmaceutically acceptable salt thereof.

2. R １ and R ２ together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe): 【Transformation 3】 (wherein Rx and Ry each independently represent an oxo group, an optionally substituted C ６－１４ an aryloxy group or an optionally substituted C １－６ alkyl group, wherein two Rx and two Ry are each independently taken together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C ３－８ may form a cycloalkane; Rz is a hydrogen atom or an optionally substituted C １－６ is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R １ and R ２ are each independently C １－６ C optionally substituted with an alkoxy group １－６ is an alkyl group; f R ３ are each independently C １－６ Alkyl group, C ２－６ Alkenyl group, —COR ｇ (R ｇ is C １－６ alkyl group), C ６－１４ Aryl group, 5- to 8-membered aromatic heterocyclic group, —NR ａ１ R ｂ１ (R ａ１ and R ｂ１ is as described below), -OR ｃ１ (R ｃ１ represents a halogen atom; f represents an integer of 0 to 3; R ３ａ is a hydrogen atom or C １－６ represents an alkyl group; A is an optionally substituted divalent C ３－１４ a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or an optionally substituted 3- to 8-membered heterocycloalkylene group; Q is C １－６ Alkyl group, C ３－１４ a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R ４ (where R ４ each independently represents an optionally substituted C １－６ an alkyl group, an optionally substituted 5- to 8-membered aromatic heterocyclic group, a nitro group, —NR ａ２ R ｂ２ (R ａ２ and R ｂ２ is as described below), -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ R ｃ３ (R ｃ３ is as described below), -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ is as defined below, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterobridged ring group), or —COR ｅ (R ｅ is an optionally substituted C １－６ (Alkyl group) optionally substituted with; R ａ１ ~R ａ３ , and R ｂ１ ~R ｂ３ are each independently a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ２－８ Alkynyl group, optionally substituted C ３－14 a hydrocarbon ring group, an optionally substituted 3- to 8-membered heterocycloalkyl group, or —COR f (R f is C １－６ alkyl group, optionally substituted C ３－８ a hydrocarbon ring group, or C ３－８ heterocycloalkyl group); R ｃ１ ~R ｃ３ are each independently a hydrogen atom, an optionally substituted C １－６ Alkyl group, -COR ｈ (R h is C １－６ alkyl group), or optionally substituted C ６－１４ is an aryl group, 2. The compound of claim 1 or a pharmaceutically acceptable salt thereof.

3. R １ and R ２ together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe): 【Chemistry 4】 (Wherein Rx and Ry are each independently an oxo group, C ６－１４ C optionally substituted with an aryloxy group or a hydroxyl group １－６ alkyl group, wherein two Rx and two Ry are each independently taken together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C ３－８ may form a cycloalkane; Rz is a hydrogen atom or C １－６ is an alkyl group; n1 and n2 each independently represent an integer of 0 to 3; or R １ and R ２ are each independently C １－６ C optionally substituted with an alkoxy group １－６ is an alkyl group; f R ３ are each independently C １－６ Alkyl group, C ２－６ Alkenyl group, —COR ｇ (R ｇ is C １－６ alkyl group), C ６－１４ an aryl group, a 5- to 8-membered aromatic heterocyclic group, —OR ｃ１ (R ｃ１ represents a halogen atom; f represents an integer of 0 to 3; R ３ａ is a hydrogen atom or C １－６ represents an alkyl group; A is a divalent C optionally substituted with a hydroxyl group ３－１４ a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; Q is C １－６ Alkyl group, C ３－１４ a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or a 5- to 8-membered aromatic heterocyclic group, each of which may be the same or different and which is represented by 1 to 3 R ４ (where R ４ are each independently C １－６ Alkoxy group, C ６－１４ Aryl-C １－６ C optionally substituted with a group selected from an alkoxy group, a hydroxyl group, and a halogen atom １－６ Alkyl group, C １－６ a 5- to 8-membered aromatic heterocyclic group optionally substituted with an alkyl group, a nitro group, —NR ａ２ R ｂ２ (R ａ２ and R ｂ２ is as described below), -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ R ｃ３ (R ｃ３ is as described below), -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ is as defined below, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterobridged ring group), or —COR ｅ (R ｅ is C １－６ (Alkyl group) optionally substituted with; M １ is C １－６ Alkyl group or C ６－１４ C optionally substituted with an aryl group １－４ Alkylene group R ａ１ ~R ａ３ , and R ｂ１ ~R ｂ３ are each independently a hydrogen atom, C １－６ C optionally substituted with an alkoxy group １－６ Alkyl group, C ２－８ Alkynyl group, C ３－１４ a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or —COR ｆ (R ｆ is C １－６ Alkyl group, C ３－８ a hydrocarbon ring group, or C ３－８ heterocycloalkyl group); R ｃ１ ~R ｃ３ are each independently a hydrogen atom, C １－６ Alkyl group, -COR ｈ (R h is C １－６ alkyl group), or C ６－１４ is an aryl group, 2. The compound of claim 1 or a pharmaceutically acceptable salt thereof.

4. (1) 1) g represents 1; 2) (i) M １ C optionally substituted by a C 1-6 alkyl group or a C 6-14 aryl group ２－４ Indicates an alkylene group; (ii) M １ But -(CH ２ )—and A represents an optionally substituted divalent non-aromatic hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; or (iii) M １ But -(CH ２ ) - and A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q is C １－６ represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and which is represented by 1 to 3 R ４ (where R ４ may be substituted with as defined in claim 1 ); or (2) 1) g is 0; 2) (i) M １ C optionally substituted by a C 1-6 alkyl group or a C 6-14 aryl group ２－４ Indicates an alkylene group; (ii) M １ But -(CH ２ )—and Q is C １－６ represents an alkyl group, a non-aromatic hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group is the same or different and has 1 to 3 R ４ (where R ４ may be substituted with as defined in claim 1 ); or (iii) M １ But -(CH ２ ) - and Q represents an aromatic hydrocarbon ring group, and the group is composed of 1 to 3 R ４ Here, R ４ each independently represents an optionally substituted C １－６ Alkyl group, nitro group, —NR ａ２ R ｂ２ (R ａ２ and R ｂ２ is as described below), -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ R ｃ３ (R ｃ３ is as described below), -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ is as defined below, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or —COR ｅ (R ｅ is an optionally substituted C １－６ It may be substituted with an alkyl group; R ａ2 ~R ａ3 , and R ｂ2 ~R ｂ３ are each independently a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ２－８ an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or —COR f (R f is C １－６ an alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group; R ｃ２ ~R ｃ３ are each independently a hydrogen atom, an optionally substituted C １－６ Alkyl group, -COR ｈ (R ｈ is C １－６ an alkyl group), or an optionally substituted aryl group; 2. The compound of claim 1 or a pharmaceutically acceptable salt thereof.

5. R １ and R ２ together with the nitrogen atom to which they are attached form the following formula (IIa): 【Transformation 5】 (wherein Rx is a C １－６ alkyl group, where two Rx together with the carbon atom to which they are attached form a 3- to 8-membered heterocycloalkane or C ３－８ may form a cycloalkane; n1 represents an integer of 0 to 3; forming a group represented by The compound according to any one of claims 1 to 4 or a pharmaceutically acceptable salt thereof.

6. (1) g represents 1; (2) (i) M １ C optionally substituted by a C 1-6 alkyl group or a C 6-14 aryl group ２－４ Indicates an alkylene group; (ii) M １ But -(CH ２ )—and A represents an optionally substituted divalent non-aromatic hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; or (iii) M １ But -(CH ２ ) - and A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q is C １－６ represents an alkyl group, a hydrocarbon ring group, or a heterocycloalkyl group, each of which may be the same or different and which is represented by 1 to 3 R ４ (where R ４ is optionally substituted with as defined in claim 1 ); 10. The compound of claim 1 or 4, or a pharmaceutically acceptable salt thereof.

7. g is 1; f R ３ are each independently -OR ｃ１ (R ｃ１ as described below); f represents an integer of 0 to 3; R ３ａ is a hydrogen atom or C １－６ represents an alkyl group; A is C ３－８ Cycloalkylene group, C ３－８ Cycloalkenylene group, C ６－１４ an arylene group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; Q is C ３－８ Cycloalkyl group or C ６－１４ aryl groups, each of which may be the same or different and may have 1 to 3 R ４ (where R ４ are each independently C １－６ Alkoxy group, C ６－１４ Aryl-C １－６ C optionally substituted with an alkoxy group, a hydroxyl group, or a halogen atom １－６ Alkyl group; Nitro group; —NR ａ２ R ｂ２ (R ａ２ and R ｂ２ is as described below); -OR ｃ２ (R ｃ２ is as described below); -CO ２ R ｃ３ (R ｃ３ is as described below); -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ is as defined below, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterobridged ring group; a cyano group; or a halogen atom); M １ is -(CH ２ ) ｉ - (wherein i is 1 to 4); M ２ is -(CH ２ ) ｊ１ -, -(CH ２ ) ｊ２ -O-(CH ２ ) ｊ３ --, --CONR ａ４ -, -NR ａ５ CO-, or -(CH ２ ) ｊ４ -CO-(CH ２ ) ｊ５ - (wherein, R ａ４ ~R ａ５ is as defined below, and j1 to j5 each independently represent an integer of 0 to 4; R ａ２ ~R ａ5 , and R ｂ２ ~R ｂ３ are each independently a hydrogen atom, C １－６ C optionally substituted with an alkoxy group １－６ Alkyl group, C ２－８ Alkynyl group, C ３－１４ a hydrocarbon ring group, a 3- to 8-membered heterocycloalkyl group, or —COR ｆ (R ｆ is C １－６ Alkyl group, C ３－８ a hydrocarbon ring group, or C ３－８ heterocycloalkyl group); R ｃ1 ~R ｃ3 are each independently a hydrogen atom, C １－６ an alkyl group or —COR ｈ (R ｈ is C １－６ alkyl group), The compound according to any one of claims 1 to 4 or a pharmaceutically acceptable salt thereof.

8. R １ and R ２ together with the nitrogen atom to which they are attached form the following formula (IIa): 【Transformation 6】 (wherein n1 represents 0) forming a group represented by 8. The compound of claim 7 or a pharmaceutically acceptable salt thereof.

9. (1) g is 0; (2) (i) M １ C optionally substituted by a C 1-6 alkyl group or a C 6-14 aryl group ２－４ Indicates an alkylene group; (ii) M １ But -(CH ２ )—and Q is C １－６ alkyl groups, non-aromatic hydrocarbon ring groups, heterocycloalkyl groups, or an aromatic heterocyclic group, each of which may be the same or different and may have 1 to 3 R ４ (where R ４ may be substituted with as defined in claim 1 ); or (iii) M １ But -(CH ２ ) - and Q represents an aromatic hydrocarbon ring group, and the group is composed of 1 to 3 R ４ (where R ４ each independently represents an optionally substituted C １－６ Alkyl group, nitro group, —NR ａ２ R ｂ２ (R ａ２ and R ｂ２ is as described below), -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ R ｃ３ (R ｃ３ is as described below), -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ is as defined below, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or —COR ｅ (R ｅ is an optionally substituted C １－６ It may be substituted with an alkyl group; R ａ2 ~R ａ3 , and R ｂ2 ~R ｂ３ are each independently a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ２－８ an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or —COR f (R f is C １－６ an alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group; R ｃ2 ~R ｃ３ are each independently a hydrogen atom, an optionally substituted C １－６ Alkyl group, -COR ｈ (R ｈ is C １－６ an alkyl group), or an optionally substituted aryl group; 10. The compound of claim 1 or 4, or a pharmaceutically acceptable salt thereof.

10. g is 0; f R ３ But, -OR ｃ１ (R ｃ１ is as described below); f is an integer from 0 to 3; Q is C １－６ Alkyl group, C ３－１４ Cycloalkyl group, C ６－１４ an aryl group or a 5- to 14-membered spirocyclic group, each of which may be the same or different and which has 1 to 3 R ４ (where R ４ are each independently C １－６ alkyl group, -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ R ｃ３ (R ｃ３ is as described below), -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ is as defined below, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group), or —COR ｅ (R ｅ is C １－６ optionally substituted with alkyl groups); M １ But C １－６ C optionally substituted with an alkyl group １－４ represents an alkylene group; M ２ But -(CH ２ ) ｊ１ - or - (CH ２ ) ｊ２ -O-(CH ２ ) ｊ３ - (wherein j1 to j3 each independently represent an integer of 0 to 4); R ａ3 , and R ｂ３ are each independently a hydrogen atom or C ３－８ represents a cycloalkyl group, and R ｃ１ ~R ｃ３ are each independently a hydrogen atom or C １－６ The compound according to any one of claims 1 to 4, or a pharmaceutically acceptable salt thereof, which is an alkyl group.

11. R １ and R ２ together with the nitrogen atom to which they are attached form the following formula (IIa): 【Transformation 7】 (wherein n1 represents 0) forming a group represented by 11. The compound of claim 10 or a pharmaceutically acceptable salt thereof.

12. g is 1; f R ３ But, -OR ｃ１ (R ｃ１ represents a hydrogen atom or -COR ｈ (R ｈ is C １－６ alkyl group); f is 0 or 1; R ３ａ is a hydrogen atom or C １－６ is an alkyl group; A is C ３－８ is a cycloalkylene group; Q is C ６－１４ aryl groups, each of which may be the same or different and may have 1 to 3 R ４ (where R ４ are each independently C １－６ Alkoxy group, C ６－１４ Aryl-C １－６ C optionally substituted with an alkoxy group, a hydroxyl group, or a halogen atom １－６ alkyl groups; -NR ａ２ R ｂ２ (R ａ２ and R ｂ２ are each independently a hydrogen atom, C １－６ an alkyl group, or —COR ｆ (R ｆ is C １－６ Alkyl group, C ３－８ a hydrocarbon ring group, or C ３－８ heterocycloalkyl groups); -CO ２ R ｃ３ (R ｃ３ is C １－６ alkyl group); -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ are each independently a hydrogen atom, C １－６ C optionally substituted with an alkoxy group １－６ Alkyl group, C ２－８ Alkynyl group, C ３－８ a hydrocarbon ring group or a 3- to 8-membered heterocycloalkyl group, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group or a 6- to 10-membered heterobridged ring group; or (indicating halogen atoms) optionally substituted with; M １ is -(CH ２ ) ｉ - (wherein i is 1 to 4); M ２ は、-(CH ２ ) ｊ１ -、-(CH ２ ) ｊ２ -O-(CH ２ ) ｊ３ - (wherein j1 to j3 each independently represent an integer of 0 to 4).

9. The compound of claim 8 or a pharmaceutically acceptable salt thereof.

13. g is 0; f R ３ is a hydroxyl group; f is an integer of 0 or 1; R ３ａ is a hydrogen atom; Q is C ３－１４ Cycloalkyl group, C ６－１４ an aryl group or a 5- to 14-membered spirocyclic group; M １ But C １－６ C optionally substituted with an alkyl group １－４ an alkylene group; M ２ But -(CH ２ ) ｊ１ - (wherein j1 represents 0) 12. The compound of claim 11 or a pharmaceutically acceptable salt thereof.

14. The compound represented by formula (I) is one or more compounds selected from the group of compounds represented by the following structural formulas: The compound according to any one of claims 1 to 4 or a pharmaceutically acceptable salt thereof. 【Transformation 8】 【Chemistry 9】 【Chemistry 10】 【Chemistry 11】 【Chemistry 12】 【Chemistry 13】 【Chemistry 14】 【Chemistry 15】

15. g is 1; f is 0; R ３ａ is a hydrogen atom; A is C ３－８ is a cycloalkylene group; Q is C ６－１４ aryl groups, each of which may be the same or different and may have 1 to 3 R ４ (where R ４ is -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ taken together with the nitrogen atom to which they are attached form a 3- to 8-membered heterocycloalkyl group. optionally substituted with; M １ is -(CH ２ ) ｉ - (wherein i is 1 to 4); M ２ is -(CH ２ ) ｊ１ - or - (CH ２ ) ｊ２ -O-(CH ２ ) ｊ３ - (wherein j1 to j3 each independently represent an integer of 0 to 4).

13. The compound of claim 12 or a pharmaceutically acceptable salt thereof.

16. g is 0; f is 0; R ３ａ is a hydrogen atom; Q is a 5- to 14-membered spirocyclic group; M １ But C １－４ an alkylene group; M ２ But -(CH ２ ) ｊ１ - (wherein j1 represents 0) That is, 14. The compound of claim 13 or a pharmaceutically acceptable salt thereof.

17. Formula (I): 【Chemistry 16】 [In the formula, R １ and R ２ are taken together with the nitrogen atom to which they are attached to form the following formulae (IIa) to (IIe): 【Chemistry 17】 (In the formula, Rx and Ry each independently represent an oxo group, an optionally substituted aryloxy group, or an optionally substituted C １－６ an alkyl group, wherein two Rx and two Ry may each independently be joined together with the carbon atom to which they are attached to form a heterocycloalkane or a cycloalkane; Rz is a hydrogen atom or an optionally substituted C １－６ represents an alkyl group; n1 and n2 each independently represent an integer of 0 to 3. or R １ and R ２ each independently represents a C 1-6 optionally substituted by an alkoxy group; １－６ represents an alkyl group; f R ３ are each independently C １－６ Alkyl group, C ２－６ Alkenyl group, —COR ｇ (R ｇ is C １－６ alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR ａ１ R ｂ１ (R ａ１ and R ｂ１ is as described below), -OR ｃ１ (R ｃ１ represents a halogen atom; f represents an integer of 0 to 3; R ３ａ is a hydrogen atom, C １－６ Alkyl group, C ２－６ Alkenyl group, —COR ｇ (R ｇ is C １－６ alkyl group), hydrocarbon ring group, aromatic heterocyclic group, -NR ａ１ R ｂ１ (R ａ１ and R ｂ１ is as described below), -OR ｃ１ (R ｃ１ represents a halogen atom; A represents an optionally substituted divalent hydrocarbon ring group, a divalent fused aromatic heterocyclic group, or an optionally substituted heterocycloalkylene group; g represents 0 or 1; Q is C １－６ represents an alkyl group, a hydrocarbon ring group, a heterocycloalkyl group, or an aromatic heterocyclic group, and each group is the same or different and has 1 to 3 R ４ (where R ４ each independently represents an optionally substituted C １－６ an alkyl group, an optionally substituted aromatic heterocyclic group, a nitro group, —NR ａ２ R ｂ２ (R ａ２ and R ｂ２ is as described below), -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ R ｃ３ (R ｃ３ is as described below), -CONR ａ３ R ｂ３ (R ａ３ and R ｂ３ is as defined below, where R ａ３ and R ｂ３ may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group or a heterobridged ring group), or —COR ｅ (R ｅ is an optionally substituted C １－６ (Alkyl group) optionally substituted with; M １ is a C 1-6 alkyl group or a C 6-14 aryl group optionally substituted with １－４ represents an alkylene group; M ２ is -(CH ２ ) ｊ１ -, -(CH ２ ) ｊ２ -O-(CH ２ ) ｊ３ --, --CONR ａ４ -, -NR ａ５ CO-, -(CH ２ ) ｊ４ -CO-(CH ２ ) ｊ５ -, -(CH ２ ) ｊ６ -CH(R)-(CH ２ ) ｊ７ -, -(CH ２ ) ｊ８ -S-(CH ２ ) ｊ９ - or -NR ａ６ - (wherein, R ａ４ ~R ａ６ is as described below, and j1 to j9 each independently represent an integer of 0 to 4; R represents a hydroxyl group or an aryl group; R ａ１ ~R ａ６ , and R ｂ１ ~R ｂ３ are each independently a hydrogen atom, an optionally substituted C １－６ alkyl group, optionally substituted C ２－８ an alkynyl group, an optionally substituted hydrocarbon ring group, an optionally substituted heterocycloalkyl group, or —COR f (R f is C １－６ an alkyl group, an optionally substituted hydrocarbon ring group, or a heterocycloalkyl group; R ｃ１ ~R ｃ３ are each independently a hydrogen atom, an optionally substituted C １－６ Alkyl group, -COR ｈ (R h is C １－６ alkyl group), or an optionally substituted aryl group. however, (1) M １ Ga-(CH ２ )-, g is 0, and M ２ Ga-(CH ２ ) ｊ１ -, and when j1 is 0 and Q is benzene, R ４ is not a pyrazolyl group substituted with a methyl group. (2) M １ Ga-(CH ２ )-, g is 1, A is benzene, and M ２ But -(CH ２ ) ｊ１ -, and when j1 is 0 and Q is pyrazole, R ４ is not a methyl group. A pharmaceutical comprising, as an active ingredient, a compound represented by the formula:

18. The pharmaceutical agent according to claim 17, which is an autophagy function activator.

19. The pharmaceutical agent according to claim 17, which is a preventive or therapeutic agent for a disease caused by a decrease in autophagy function or a disease whose pathology is suppressed or ameliorated by an increase in autophagy function.

20. The pharmaceutical composition of claim 17, which is a preventive or therapeutic agent for neurodegenerative diseases; cardiovascular diseases; musculoskeletal diseases; skeletal diseases; lung diseases; kidney diseases; metabolic syndromes; liver lesions; immune, inflammatory and immune-related diseases; eye diseases; reproductive system dysfunction; congenital multisystem disorders; and / or cancer.

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