Autophagy function-activating compound

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

Autophagy-activating compounds

[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.

[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 the like. 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 in which the 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 to prevent or treat diseases and symptoms caused in part by impaired autophagy, or diseases and symptoms whose pathology can be suppressed or improved by enhancing autophagy (Patent Documents 1 to 3). However, medical practice demands drugs that activate a wider variety of autophagy functions, and for this reason, the creation of compounds that activate autophagy with structures that are different from conventional compounds 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.

[0004] JP 2023-174643 A International Publication No. 2022 / 054926 International Publication No. 2022 / 054927 International Publication No. 2011 / 019060

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

[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]

[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]

[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 join together to form a heterocycloalkane or a cycloalkane together with the carbon atom to which they are attached; 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 １ and R ２ each independently represents an optionally substituted C 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 (Rａ１ and R ｂ１ is as described below), -OR ｃ１ (R ｃ１ represents an integer of 0 to 3; 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 substituted or unsubstituted divalent hydrocarbon ring group, a fused aromatic heterocyclic group, or a heterocycloalkylene group; g represents 0 or 1; Q represents 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 ｅis an optionally substituted C １－６ M may be substituted with an alkyl group; １ is an optionally substituted C 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 are 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(1) M represents an alkyl group, or an aryl group which may be substituted. 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):

[0012]

[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 taken together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C ３－８ Rz is a hydrogen atom or an optionally substituted C １－６ 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 alkyl group; f R ３ are each independently C １－６ Alkyl group, C ２－６ Alkenyl group, —COR ｇ (R ｇ is C１－６ 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 an integer of 0 to 3; ３ａ is a hydrogen atom or C １－６ A represents 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; 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 R represents an alkyl group; ａ１ ~R ａ３ , and Rｂ１ ~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 [3] The compound according to the above-mentioned [1], or a pharmaceutically acceptable salt thereof, wherein R is an aryl group. １ and R ２ together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe):

[0014]

[0015] (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 Rz may form a cycloalkane; １－６ 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 C１－６ C optionally substituted with an alkoxy group １－６ 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 an integer of 0 to 3; ３ａ is a hydrogen atom or C １－６ A represents 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; 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 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 heterobridged ring group), or —COR ｅ (R ｅ is C １－６ M may be substituted with an alkyl group; 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 The compound according to the above-mentioned [1] or [2], wherein R is an aryl group, or a pharmaceutically acceptable salt thereof.

[0016] [4] (1) 1) g represents 1; 2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; 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)-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q represents 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 may have 1 to 3 R ４ (where R ４ may be substituted with (as described in [1] above); or (2) 1) g represents 0; 2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; 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 is optionally substituted with (as described in [1] above); or (iii) M １ But -(CH ２ )-, 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 C１－６ R may be substituted with an alkyl group; 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 The compound according to the above-mentioned [1], or a pharmaceutically acceptable salt thereof, wherein R represents an alkyl group, an optionally substituted aryl group, or an optionally substituted aryl group.

[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] The following formula (I):

[0018]

[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]

[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 join together to form a heterocycloalkane or a cycloalkane together with the carbon atom to which they are attached; Rz is a hydrogen atom or an optionally substituted C１－６ 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 １ and R ２ each independently represents an optionally substituted C 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 an integer of 0 to 3; 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, as described below; (1) 1) g represents 1; 2) (i) M １ is an optionally substituted C ２－４ 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 represents a hydroxyl group or an aryl group, R ａ４ ~R ａ６ are as defined 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 is the same or different and has 1 to 3 R ４ (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 (ii) M １ is -(CH ２ )- and M２ is as defined above; 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 represents 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 (R ４ is as defined above); or (iii) M １ But -(CH ２ )- and M ２ is as defined above; A represents an optionally substituted divalent aromatic hydrocarbon ring group; and Q represents 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 may have 1 to 3 R ４ (R ４ is as defined above); or (2) 1) g represents 0; 2) (i) M １ is an optionally substituted C ２－４ represents an alkylene group; M ２ is as defined above; 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 is the same or different and has 1 to 3 R ４ (R ４ (ii) M １ is -(CH ２ )- and M ２ is as defined above; 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 (R ４ is as defined above); or (iii) M １ But -(CH ２ )- and M ２is as defined above; and Q represents an aromatic hydrocarbon ring group, which 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 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 R may be substituted with an alkyl group; 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 １－６or a pharmaceutically acceptable salt thereof.

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

[0023]

[0024] (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 The compound according to any one of the above [1], [2], [3], [4], and [4A], or a pharmaceutically acceptable salt thereof, wherein n1 represents an integer of 0 to 3, and n2 represents an integer of 0 to 3; and n3 represents an integer of 0 to 3, and n4 represents an integer of 0 to 3;

[0025] [6] (1) g represents 1; (2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; 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 )-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q represents 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 may have 1 to 3 R ４ (where R ４ [7] The compound according to any one of the above [1], [4], [4A] or [5], or a pharmaceutically acceptable salt thereof. [7] g is 1; f R ３ are each independently -ORｃ１ (R ｃ１ is as described below); f represents an integer of 0 to 3; R ３ａ is a hydrogen atom or C １－６ A represents an alkyl group; ３－８ Cycloalkylene group, C ３－８ Cycloalkenylene group, C ６－１４ Q is an arylene group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; 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 substituted with 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 --, --CONRａ４ -, -NR ａ５ CO-, or -(CH ２ ) ｊ４ -CO-(CH ２ ) ｊ５ - (wherein, 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 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 [8] R is a phenyl group, or a phenyl group, or a pharmaceutically acceptable salt thereof. １ and R ２ together with the nitrogen atom to which they are attached form the following formula (IIa):

[0026]

[0027] (wherein n1 represents 0) or a pharmaceutically acceptable salt thereof. [9] (1) g represents 0; (2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; １ But -(CH ２ )- and Q is C １－６represents 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 is optionally substituted with (as described in [1] above); or (iii) M １ But -(CH ２ )-, 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 R may be substituted with an alkyl group; 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 Rｃ2 ~R ｃ３ are each independently a hydrogen atom, an optionally substituted C １－６ Alkyl group, -COR ｈ (R ｈ is C １－６

[10] The compound according to any one of the above [1], [4], [4A], or [5], or a pharmaceutically acceptable salt thereof, wherein g is 0; f R ３ But, -OR ｃ１ (R ｃ１ is as defined below); f is an integer of 0 to 3; Q is C １－６ Alkyl group, C ３－１４ Cycloalkyl group, C ６－１４ aryl group or 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), 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 M may be substituted with an alkyl group; 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

[11] The compound according to any one of the above [1], [2], [3], [4], [4A], [5] or [9], or a pharmaceutically acceptable salt thereof, wherein R is an alkyl group. １ and R ２ together with the nitrogen atom to which they are attached form the following formula (IIa):

[0028]

[0029] (wherein n1 represents 0)

[12] The compound according to the above-mentioned

[10] or a pharmaceutically acceptable salt thereof, wherein g is 1; 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 A is an alkyl group; ３－８ Q is a cycloalkylene group; 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 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; —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 ｆis C １－６ Alkyl group, C ３－８ a hydrocarbon ring group, or C ３－８ heterocycloalkyl group); 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 C ３－８ heterocycloalkyl group, where R ａ３ and R ｂ３ may be joined 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 may be substituted with 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 - (wherein j1 to j3 each independently represent an integer of 0 to 4), or a pharmaceutically acceptable salt thereof according to the above-mentioned [8].

[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 is an alkylene group; M ２ But -(CH ２ ) ｊ１- (wherein j1 represents 0), or a pharmaceutically acceptable salt thereof.

[14] The compound according to any of the above [1] to

[13] , wherein the compound represented by formula (I) is one or more compounds selected from the group of compounds represented by the following structural formulas:

[0030]

[0031]

[0032]

[0033]

[0034]

[0035]

[0036]

[0037]

[0038]

[15] g is 1; f is 0; R ３ａ is a hydrogen atom; ３－８ Q is a cycloalkylene group; 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 are optionally substituted with a 3- to 8-membered heterocycloalkyl group together with the nitrogen atom to which they are attached; 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), 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 -(CH ２ ) ｊ１ - (wherein j1 represents 0) or a pharmaceutically acceptable salt thereof.

[0039]

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

[16] above or a pharmaceutically acceptable salt thereof.

[18] The pharmaceutical according to

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

[19] The pharmaceutical according to

[17] above, which is a preventive or therapeutic agent for diseases caused by decreased autophagy function or diseases whose pathology is suppressed or ameliorated by increased autophagy function.

[20] The pharmaceutical according to

[17] above, which is a preventive or therapeutic agent for neurodegenerative diseases; cardiovascular diseases; musculoskeletal diseases; skeletal diseases; pulmonary 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 function 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 can be suppressed or ameliorated by enhancing autophagy function, comprising administering an effective amount of the compound according to any one of [1] to

[16] above or a pharmaceutically acceptable salt thereof to the mammal in need thereof.

[23] The method for preventing or treating the disease caused by a decrease in autophagy function or whose pathology can be suppressed or ameliorated by enhancing autophagy function is neurodegenerative disease; cardiovascular disease; musculoskeletal disease; skeletal disease; pulmonary 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 the above-mentioned [1] to

[16] or a pharmaceutically acceptable salt thereof, which is used for the prevention or treatment of a disease caused by a decrease in autophagy function or a disease whose pathology can be suppressed or ameliorated by an increase in autophagy function.

[26] The compound according to

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

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

[16] above, or a pharmaceutically acceptable salt thereof, for producing an autophagy function activator.

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

[16] above, or a pharmaceutically acceptable salt thereof, for producing an agent for preventing or treating a disease caused by a decrease in autophagy function or a disease whose pathology can be suppressed or ameliorated by enhancing autophagy function.

[29] The use described in

[28] above, wherein the disease caused by a decrease in autophagy function or the disease whose pathology is 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.

[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 enhanced autophagy function.

[0041] The present invention will be described in detail below based on the following embodiments, but the present invention is not limited thereto. 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 encompassed within the scope of the present invention. Unless otherwise specified in the context, all technical and scientific terms used herein have the same meaning as commonly understood by those skilled in the art to which the present 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, 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 methodologies described in the publications that may 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 "C ａ -C ｂ ” (e.g., C １ -C ６ ) indicates that the group has a to b carbon atoms (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 ２－６Examples 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] In the present specification, 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, 1 to 4 heteroatoms selected from a nitrogen atom, a sulfur atom, and an oxygen atom as ring-constituting atoms. 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 "cycloalkyl (group)" is preferably "C ３－１４ Cycloalkyl (group)" and examples thereof include 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 ３－１４ and cycloalkenyl (group)" such as cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, and the like.

[0058] In the present specification, the "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 the present 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 (group) and cycloalkenylene (group), and divalent aromatic hydrocarbon ring groups such as arylene (group). In the present specification, the term "cycloalkylene (group)" preferably refers to "C ３－１４ Examples of the "cycloalkenylene (group)" include cyclopropylene, cyclobutylene, cyclopentylene, cyclohexylene, cycloheptylene, cyclooctylene, bicyclo[2.2.1]heptylene, bicyclo[2.2.2]octylene, bicyclo[3.2.1]octylene, and adamantylene. In the present specification, the "cycloalkenylene (group)" is preferably "C ３－１４The "arylene (group)" is preferably a cycloalkenylene (group) such as cyclopropenylene, cyclobutenylene, cyclopentenylene, cyclohexenylene, cycloheptenylene, cyclooctenylene, etc. 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 arylene (group).

[0060] In the present specification, examples of the "heterocycle" include aromatic heterocycles and non-aromatic heterocycles each containing, in addition to carbon atoms, 1 to 4 heteroatoms selected from nitrogen atoms, sulfur atoms, and oxygen atoms as ring-constituting atoms. In the present specification, "non-aromatic" includes both non-aromatic and anti-aromatic rings according to Hückel's rule.

[0061] In the present specification, 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, triazine, etc.; 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 quinidine, 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]

[0023] In the present specification, 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 include 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 "nitrogen-containing heterocycle" includes, among "heterocycles", those containing at least one nitrogen atom as a ring-constituting atom.

[0063]

[0023] 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, triazinyl, etc.; benzothiophenyl, benzofuranyl, benzimidazolyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzisothiazolyl, benzotriazolyl, imidazopyridinyl, thienopyridinyl, furopyridinyl, pyrrolopyridinyl, pyrazolopyridinyl, oxazolopyridinyl, thiazolopyridinyl, imidazopyrazinyl, imidazopyrimidinyl, thienopyrimidinyl, furopyrimidinyl, pyrrolopyrimidinyl, pyrazolopyrimidinyl, oxazolopyrimidinyl, thiazolopyrimidinyl, fused aromatic heterocyclic groups such as 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, more specifically 8- to 14-membered fused polycyclic (preferably bi- 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 ... 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, oxazepanyl, and the like; 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 a divalent group having two bonds derived from a fused polycyclic (preferably bicyclic or tricyclic) aromatic heterocycle, and preferably a divalent group 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]

[0033] 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] As used herein, the term "heterocycloalkylene (group)" refers to a divalent group having two bonds derived from a saturated "heterocycloalkane" among the above-mentioned monocyclic non-aromatic heterocyclic groups. Preferred examples include 3- to 8-membered groups. Examples include nitrogen-containing groups such as piperidine-diyl and piperazine-diyl.

[0071] In the present specification, "optionally substituted C １－６Examples of the "substituent" in the "optionally substituted group or ring" in the definitions of the compound represented by formula (I) (hereinafter referred to as compound (I)), such as "alkyl group" and "optionally substituted aromatic heterocyclic group", include substituents selected from the following [Substituent Group A]. One to five (preferably one to three) of the "substituents" may be present at substitutable positions, and when the number of substituents is two or more, the respective substituents may be the same or different. When a special explanation is given for the "substituent" in each group or ring, etc., that explanation shall be followed.

[0072] [Substituent Group A] (1) halogen atom, (2) nitro group, (3) cyano group, (4) oxo group, (5) hydroxy group, (6) optionally halogenated C １ -C ６ Alkoxy groups (e.g., methoxy, chloromethoxy, trifluoroethoxy), (7) C ６ -C １４ Aryloxy groups (e.g., phenoxy, naphthoxy), (8) C ７ -C １６ an aralkyloxy group (e.g., benzyloxy), (9) C １ -C ６ Alkyl-carbonyloxy groups (e.g., acetoxy, propanoyloxy), (10) C ６ -C １４ Aryl-carbonyloxy groups (e.g., benzoyloxy, 1-naphthoyloxy, 2-naphthoyloxy), (11) C １ -C ６alkoxy-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 a 5- to 6-membered monocyclic aromatic heterocyclic group is preferred, and a 5- to 6-membered monocyclic nitrogen-containing aromatic heterocyclic group is 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 (13) 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 C １ -C ６ Alkyl-carbonyl groups (e.g., acetyl, chloroacetyl, trifluoroacetyl), (17) C ６ -C １４ Aryl-carbonyl groups (e.g., benzoyl, 1-naphthoyl, 2-naphthoyl), (18) C １ -C ６ (19) an alkoxycarbonyl group (e.g., methoxycarbonyl, ethoxycarbonyl), (20) a carbamoyl group, (21) an amino group, (22) a mono- or di-C１ -C ６ alkylamino groups (e.g., methylamino, ethylamino, propylamino, isopropylamino, butylamino, dimethylamino, diethylamino, dipropylamino, dibutylamino, N-ethyl-N-methylamino), (22) mono- or di-C ６ -C １４ (23) an arylamino group (e.g., phenylamino), (24) C １ -C ６ Alkyl-carbonylamino groups (e.g., acetylamino, propanoylamino, butanoylamino), (25) C １ -C ６ Alkoxy-carbonylamino groups (e.g., methoxycarbonylamino, ethoxycarbonylamino, propoxycarbonylamino, butoxycarbonylamino, tert-butoxycarbonylamino), (26) optionally halogenated C １ -C ６ Alkyl groups (e.g., methyl, chloromethyl, difluoromethyl, trifluoromethyl, ethyl, 2-bromoethyl, 2,2,2-trifluoroethyl), (27) C ２ -C ６ Alkenyl groups (e.g., ethenyl, 1-propenyl, 2-propenyl, 2-methyl-1-propenyl, 1-butenyl), (28) C ２ -C ６ Alkynyl groups (e.g., ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl), (29) C ３ -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) C ３ -C １０ Cycloalkenyl groups (e.g., cyclopropenyl, cyclobutenyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl), (31) C ６ -C １４aryl groups (e.g., phenyl, naphthyl), (32) (mono- or di-C １ -C ６ (alkylamino)carbonyl groups (e.g., methylamino-carbonyl groups), and (33) C １ -C ６ Alkyl-sulfonyl groups (for example, methylsulfonyl groups).

[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 are as defined above, but in one preferred embodiment, they are taken together with the nitrogen atom to which they are bonded to form the following formulae (IIa) to (IIe):

[0075]

[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 taken together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C ３－８ Rz is a hydrogen atom or an optionally substituted C １－６ and n1 and n2 each independently represent an integer of 0 to 3; or in a more preferred embodiment, Rx is an 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 Ry may form a cycloalkane; Ry may be an oxo group or an optionally substituted C ６－１４ an aryloxy group, and Rz is a hydrogen atom or an optionally substituted C １－６and n1 and n2 each independently represent an integer of 0 to 3; or a more preferred embodiment is a group represented by any one of the following formulae (IIa) to (IIe): (wherein Rx is a 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 Ry may form a cycloalkane; ６－１４ an aryloxy group; Rz is a hydrogen atom or C １－６ 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 a group represented by the following formula (IIa):

[0077]

[0078] (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 n1 is an integer of 0 to 3, and n1 is preferably an integer of 0 to 2, more preferably 0, or (2) another preferred embodiment is a group represented by R １ and R ２ are each independently C １－６ C optionally substituted with an alkoxy group １－６ An embodiment in which the group is an alkyl group is exemplified.

[0079] f R ３ are as defined above, but in a preferred embodiment, each independently represents C １－６ Alkyl group, C ２－６ Alkenyl group, —COR ｇ (R ｇ is C １－６ alkyl group), C６－１４ an aryl group, a 5- to 8-membered aromatic heterocyclic group, —OR ｃ１ (R ｃ１ is a hydrogen atom, C １－６ an alkyl group, or —COR ｈ (R ｈ is C １－６ alkyl group), or a halogen atom; ｃ１ (R ｃ１ is a hydrogen atom, C １－６ an alkyl group, or —COR ｈ (R ｈ is C １－６ In one embodiment, f is as defined above, and in another embodiment, f is 0 or 1.

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

[0081] A is as defined above, but in a preferred embodiment, it 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; and a more preferred embodiment is a divalent C ３－１４ a hydrocarbon ring group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; 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, it is C １－６ Alkyl group, C ３－１４a 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 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 f is C １－６ Alkyl group, C ２－８ Alkynyl group, optionally substituted C ３－８ a hydrocarbon ring group, or C ３－８ -OR is a heterocycloalkyl group; ｃ２ (R ｃ２ represents 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 an aryl group); a halogen atom; a cyano group; —CO ２ R ｃ３ (R ｃ３ represents 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 C ６－１４ an aryl group; 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 ３－８a 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), 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 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 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; 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 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 a hydrocarbon ring group, or C ３－８ -OR is a heterocycloalkyl group; ｃ２ (R ｃ２ is a hydrogen atom, C１－６ Alkyl group, -COR ｈ (R h is C １－６ alkyl group) or C ６－１４ an aryl group); a halogen atom; a cyano group; —CO ２ R ｃ３ (R ｃ３ 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); 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 a 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 is an optionally substituted C １－６ (2) Another preferred embodiment of Q is optionally substituted with C ３－８ Cycloalkyl group or C ６－１４ aryl groups, each of which may be the same or different and which may have 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 １－６Alkyl 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 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 a hydrocarbon ring group, or C ３－８ a heterocycloalkyl group); ｃ２ (R ｃ２ is a hydrogen atom, C １－６ an alkyl group or —COR ｈ (R ｈ is C １－６ an alkyl group); ２ R ｃ３ (R ｃ３ is a hydrogen atom, C １－６ an 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 a hydrocarbon ring group, or C ３－８ heterocycloalkyl), where R ａ３ and R ｂ３(3) Other preferred embodiments of Q include those optionally substituted with: C １－６ Alkyl group, C ３－１４ Cycloalkyl group, C ６－１４ aryl group or 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 an alkyl group, —OR ｃ２ (R ｃ２ is a hydrogen atom or C １－６ alkyl group), halogen atom, cyano group, —CO ２ R 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 In one embodiment, the alkyl group may be substituted with an alkyl group.

[0084] M １ is as defined above, but in one preferred embodiment, １－６ Alkyl group or C ６－１４ C optionally substituted with an aryl group １－４ An embodiment in which M is an alkylene group is an example. ２ is as defined above, but in one preferred embodiment, -(CH ２ ) ｊ１ -, -(CH ２ ) ｊ２-O-(CH ２ ) ｊ３ --, --CONR ａ４ -, -NR ａ５ CO-, -(CH ２ ) ｊ４ -CO-(CH ２ ) ｊ５ - (wherein, R ａ４ ~R ａ５ each represents 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) are as follows:

[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]

[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 taken together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C ３－８ Rz is a hydrogen atom or an optionally substituted C １－６ 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 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 ６－１４Aryl 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 an integer of 0 to 3; ３ａ is a hydrogen atom or C １－６ A represents 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; 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 R represents an alkyl group; ａ１ ~R ａ３ , and R ｂ１ ~R ｂ３are 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 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 (1) M is an aryl group. 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.

[0089] [Compound A-2] In the 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]

[0091] (Wherein Rx and Ry are each independently an oxo group, C ６－１４C 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 Rz may form a cycloalkane; １－６ 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 C １－６ C optionally substituted with an alkoxy group １－６ 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 an integer of 0 to 3; ３ａ is a hydrogen atom or C １－６ A represents 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; 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 １－６Alkyl 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 M may be substituted with an alkyl group; １ 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 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 １－６alkyl group), or C ６－１４ (1) M is an aryl group. 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.

[0092] [Compound A-3] In the 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]

[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 join together to form a heterocycloalkane or a cycloalkane together with the carbon atom to which they are attached; 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 １ and R ２ each independently represents an optionally substituted C １－６ represents an alkyl group; f R ３ are each independently C１－６ 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 an integer of 0 to 3; 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, as described below; (1) 1) g represents 1; 2) (i) M １ is an optionally substituted C ２－４ 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(OH)-(CH ２ ) ｊ７ -, -(CH ２ ) ｊ８ -S-(CH ２ ) ｊ９ - or -NR ａ６ - (wherein, R ａ４ ~R ａ６are as defined 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 is the same or different and has 1 to 3 R ４ (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 (ii) M １ is -(CH ２ )- and M ２ is as defined above; 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 represents 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 (R ４ is as defined above); or (iii) M１ But -(CH ２ )- and M ２ is as defined above; A represents an optionally substituted divalent aromatic hydrocarbon ring group; and Q represents 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 may have 1 to 3 R ４ (R ４ is as defined above); or (2) 1) g represents 0; 2) (i) M １ is an optionally substituted C ２－４ represents an alkylene group; M ２ is as defined above; 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 is the same or different and has 1 to 3 R ４ (R ４ (ii) M １ is -(CH ２ )- and M ２ is as defined above; 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 (R ４ is as defined above); or (iii) M １ But -(CH ２ )- and M ２ is as defined above; and Q represents an aromatic hydrocarbon ring group, which 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 is as described below), -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ Rｃ３ (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 R may be substituted with an alkyl group; 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 The compound A-1 or A-2, or a pharmaceutically acceptable salt thereof, is selected from the group consisting of:

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

[0096]

[0097] (wherein Rx is a C 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 n1 represents an integer of 0 to 3. (wherein n1 is preferably an integer of 0 to 2, more preferably 0.) Any of the above-mentioned [Compounds A-1] to [Compounds A-3], or a pharmaceutically acceptable salt thereof, may form a cycloalkane; and n1 represents an integer of 0 to 3. (wherein n1 is preferably an integer of 0 to 2, more preferably 0.)

[0098] [Compound A-5] In the formula (I), (1) g represents 1, (2) (i) M １ is optionally substituted C ２－４ represents an alkylene group, or (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 )-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q represents 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 may have 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 ｂ３may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group), or —COR ｅ (R ｅ is an optionally substituted C １－６ R represents an alkyl group; ａ２ ~R ａ３ , and R ｂ２ ~R ｂ３ are each independently 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-mentioned [Compounds A-1] to [Compounds A-4], or pharmaceutically acceptable salts thereof.

[0099] [Compound A-6] In the formula (I), g is 1; f R ３ are each independently -OR ｃ１ (R ｃ１ is as described below); f represents an integer of 0 to 3; R ３ａ is a hydrogen atom or C １－６ A represents an alkyl group; ３－８ Cycloalkylene group, C ３－８ Cycloalkenylene group, C ６－１４ Q is an arylene group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; ３－８ Cycloalkyl group or C ６－１４ aryl groups, each of which may be the same or different and which 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 Rｂ２ (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 substituted with 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 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 a hydrocarbon ring group, or C ３－８heterocycloalkyl 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 above-mentioned [Compound A-5] or [Compound A-6], or a pharmaceutically acceptable salt thereof.

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

[0101]

[0102] (wherein n1 represents 0) The compound according to the above [Compound A-6] or a pharmaceutically acceptable salt thereof, which forms a group represented by the following formula:

[0103] [Compound A-8] (1) g is 0; (2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; 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 (iii) M １ But -(CH ２ )-, 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 ｃ２as 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 R may be substituted with an alkyl group; 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 １－６ 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 The above-mentioned [Compound A-5] or [Compound A-6], or a pharmaceutically acceptable salt thereof, wherein R represents an alkyl group, an optionally substituted aryl group, or an optionally substituted aryl group.

[0104] [Compound A-9] g is 0; f R ３ But, -OR ｃ１ (R ｃ１ is as defined below); f is an integer of 0 to 3; Q is C １－６ Alkyl group, C ３－１４ Cycloalkyl group, C ６－１４aryl group or 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), 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 M may be substituted with an alkyl group; 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 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 together with the nitrogen atom to which they are attached form the following formula (IIa):

[0106]

[0107] (wherein n1 represents 0) The compound according to the above [Compound A-9] or a pharmaceutically acceptable salt thereof, which forms a group represented by the following formula:

[0108] [Compound A-11] 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 A is an alkyl group; ３－８ Q is a cycloalkylene group; 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 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; —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 group); 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 ３－８a hydrocarbon ring group, or C ３－８ heterocycloalkyl group, where R ａ３ and R ｂ３ may be joined 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 may be substituted with 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 - (wherein j1 to j3 each independently represent an integer of 0 to 4), The compound according to the above [Compound A-7] or a pharmaceutically acceptable salt thereof.

[0109] [Compound A-11] 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), The compound according to the above [Compound A-10] or a pharmaceutically acceptable salt thereof.

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

[0111]

[0112]

[0113]

[0114]

[0115]

[0116]

[0117]

[0118]

[0119] In this embodiment, compound (I) can be used in either its free form or its pharmaceutically acceptable salt form. Those skilled in the art can carry out the present invention by appropriately selecting from either form, taking into account the properties of the individual compound (I) used. Examples of pharmaceutically acceptable salts include salts with acids such as salts with inorganic acids (e.g., hydrochloride, hydrobromide, sulfate, phosphate), salts with organic acids (e.g., acetate, fumarate, oxalate, citrate, methanesulfonate, benzenesulfonate, tosylate, maleate), salts with bases (e.g., alkali metal salts (e.g., sodium salt, potassium salt), alkaline earth metal salts (e.g., calcium salt), salts with amino acids (e.g., 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]

[0123] (In the formula, Rx and Ry each independently represent an oxo group, an optionally substituted aryloxy group, or an optionally substituted C １－６represents an alkyl group, wherein two Rx and two Ry may each independently join together to form a heterocycloalkane or a cycloalkane together with the carbon atom to which they are attached; 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 １ and R ２ each independently represents an optionally substituted C １－６ represents an alkyl group; f R ３ are each independently -NR ａ１ R ｂ１ (R ａ１ and R ｂ１ is as described below), -OR ｃ１ (R ｃ１ represents an integer of 0 to 3; ３ａ represents a hydrogen atom; A represents an optionally substituted divalent hydrocarbon ring group or an optionally substituted heterocycloalkylene group; g represents 0 or 1; Q represents 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 ｂ３may be taken together with the nitrogen atom to which they are attached to form a heterocycloalkyl group), or —COR ｅ (R ｅ is an optionally substituted C １－６ M may be substituted with an alkyl group; 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-, -(CH ２ ) ｊ４ -CO-(CH ２ ) ｊ５ -, -(CH ２ ) ｊ６ -CH(OH)-(CH ２ ) ｊ７ - or -NR ａ６ - (wherein, 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 are each independently 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 aryl group which may be substituted, provided that: (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 ４is 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.

[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]

[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 taken together with the carbon atom to which they are attached to form a 3- to 8-membered heterocycloalkane or C ３－８ Rz is a hydrogen atom or an optionally substituted C １－６ 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 A is an optionally substituted divalent C ３－１４ Q is a hydrocarbon ring group or an optionally substituted 3- to 8-membered heterocycloalkylene group; 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 １－６an 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 —COR ｅ (R ｅ is an optionally substituted C １－６ R may be substituted with an alkyl group; 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 is an optionally substituted C ３－８ hydrocarbon ring group); R ｃ１ ~R ｃ３ are each independently a hydrogen atom, an optionally substituted C １－６ an alkyl group or an optionally substituted C ６－１４ The compound according to the above [Compound B-1], or a pharmaceutically acceptable salt thereof, wherein R is an aryl group.

[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]

[0129] (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 Rz may form a hydrogen atom or C １－６ 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 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; 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 a C optionally substituted with a group selected from 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 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 R represents an alkyl group; 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 The compound according to the above [Compound B-1] or [Compound B-2], or a pharmaceutically acceptable salt thereof, wherein R is an aryl group.

[0130] [Compound B-4] (1) 1) g represents 1; 2) (i) M １ But -(CH ２ ) ｉ - (wherein i is 2 to 4); (ii) M １ But -(CH ２ )-, and A represents an optionally substituted divalent non-aromatic hydrocarbon ring group or an optionally substituted heterocycloalkylene group; or (iii) M １ But -(CH ２ )-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q represents 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 may have 1 to 3 R ４ (where R ４ may be substituted with (as described in [Compound B-1] above); or (2) 1) g represents 0; 2) (i) M １ But -(CH ２ ) ｉ - (wherein i is 2 to 4); (ii) M １But -(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 described in [Compound B-1] above); or (iii) M １ But -(CH ２ )-, and Q is the same or different and is 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 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 —COR ｅ (R ｅ is an optionally substituted C １－６ alkyl group), R ａ2 ~R ａ3 , and R ｂ2 ~R ｂ３ are each independently 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 C１－６ The compound according to the above [Compound B-1], or a pharmaceutically acceptable salt thereof, wherein R represents an alkyl group or an optionally substituted aryl group.

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

[0132] [Compound B-4A] In the 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]

[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 join together to form a heterocycloalkane or a cycloalkane together with the carbon atom to which they are attached; Rz is a hydrogen atom or an optionally substituted C １－６ n1 and n2 each independently represent an integer of 0 to 3, or １ and R ２ each independently represents an optionally substituted C １－６ represents an alkyl group; f R ３ are each independently -NR ａ１ R ｂ１ (R ａ１ and R ｂ１ is as described below), -OR ｃ１ (R ｃ１ represents an integer of 0 to 3; ３ａ represents a hydrogen atom; (1) 1) g represents 1; 2) (i) M １ is -(CH ２ ) ｉ - (wherein i is 2 to 4); M ２ is -(CH２ ) ｊ１ -, -(CH ２ ) ｊ２ -O-(CH ２ ) ｊ３ --, --CONR ａ４ -, -NR ａ５ CO-, -(CH ２ ) ｊ４ -CO-(CH ２ ) ｊ５ -, -(CH ２ ) ｊ６ -CH(OH)-(CH ２ ) ｊ７ - or -NR ａ６ - (wherein, R ａ４ ~R ａ６ are as defined 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 represents 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 (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 —COR ｅ (R ｅ is an optionally substituted C １－６(ii) M １ is -(CH ２ )- and M ２ is as defined above; A represents an optionally substituted divalent non-aromatic hydrocarbon ring group or an optionally substituted heterocycloalkylene group; and Q represents 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 (R ４ is as defined above); or (iii) M １ But -(CH ２ )- and M ２ is as defined above; A represents an optionally substituted divalent aromatic hydrocarbon ring group; and Q represents 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 may have 1 to 3 R ４ (R ４ is as defined above); or (2) 1) g represents 0; 2) (i) M １ is -(CH ２ ) ｉ - (wherein i is 2 to 4); M ２ is as defined above; 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 is the same or different and has 1 to 3 R ４ (R ４ (ii) M １ is -(CH ２ )- and M ２ is as defined above; 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 (R ４ is as defined above); or (iii) M １But -(CH ２ )- and M ２ is as defined above; and Q represents an aromatic hydrocarbon ring group, and 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 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 —COR ｅ (R ｅ is an optionally substituted C １－６ R may be substituted with an alkyl group; ａ１ ~R ａ６ , and R ｂ１ ~R ｂ３ are each independently 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 A compound represented by the formula: wherein R 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 together with the nitrogen atom to which they are attached form the following formula (IIa):

[0136]

[0137] (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 and n1 represents an integer of 0 to 3), forming a group represented by the following formula (1):

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

[0139] [Compound B-7] g is 1; f R ３ are each independently -OR ｃ１ (R ｃ１ is as described below); f represents an integer of 0 to 3; A is C ３－８ Cycloalkylene group, C ３－８ Cycloalkenylene group, C ６－１４an arylene group or a 3- to 8-membered heterocycloalkylene group; ３－８ Cycloalkyl group or C ６－１４ aryl groups, each of which may be the same or different and which may have 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 is as described below), -OR ｃ２ (R ｃ２ 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 substituted with a cyano group or a halogen atom), which may be taken together with the nitrogen atom to which they are attached to form a 3- to 8-membered heterocycloalkyl group; 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 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; ｃ1 ~R ｃ2 are each independently a hydrogen atom or C １－６the compound or a pharmaceutically acceptable salt thereof according to any one of [Compound B-1], [Compound B-2], [Compound B-3], [Compound B-4], [Compound B-4A], [Compound B-5], and [Compound B-6], wherein R is an alkyl group.

[0140] [Compound B-8] (1) g is 0; (2) (i) M １ But -(CH ２ ) ｉ - (wherein i is 2 to 4); (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 described in [Compound B-1] above); or (iii) M １ But -(CH ２ )-, and Q is the same or different and is 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 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 —COR ｅ (R ｅ is an optionally substituted C １－６ alkyl group), Rａ2 ~R ａ3 , and R ｂ2 ~R ｂ３ are each independently 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 according to any one of [Compound B-1], [Compound B-4], [Compound B-4A], and [Compound B-5] above, or a pharmaceutically acceptable salt thereof.

[0141] [Compound B-9] g is 0; f R ３ But, -OR ｃ１ (R ｃ１ is as defined below); f is an integer of 0 to 3; Q is C １－６ Alkyl group, C ３－８ a 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 alkyl group, -OR ｃ２ (R ｃ２ as described below), a halogen atom, a cyano group, —CO ２ R ｃ３ (R ｃ３ (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 M may be substituted with an alkyl group; １ But -(CH ２ )ｉ - (wherein i is 1 to 4); 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 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 compound is an alkyl group.

[0142] [Regarding the method for producing compound (I) or a pharmaceutically acceptable salt thereof] Representative embodiments 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]

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

[0146] Compound (I) or a pharmaceutically acceptable salt thereof can be produced by reacting compound (III) or a salt thereof with compound (IV) or a salt thereof. The leaving group represented by L includes a halogen atom, a sulfonyloxy group (e.g., C １－６ Examples of suitable solvents include alkylsulfonyloxy groups (e.g., methanesulfonyloxy groups). 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 appropriately select the solvent, temperature, and other conditions depending on the starting compounds to be subjected to the reaction. Any solvent that does not adversely affect the reaction can be used, and a suitable example is N,N-dimethylformamide. The reaction can be carried out in the presence of a suitable base. Suitable examples include sodium hydride, sodium tert-butoxide, potassium carbonate, and the like. The reaction can be carried out within a temperature range, for example, at room temperature, by warming, or by heating. The above provides an overview of the substitution reaction; for more details, please refer to the reaction conditions described in the various examples in the "Examples" section below.

[0147] (Manufacturing method 2)

[0148]

[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 produced 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 those skilled in the art can appropriately select the solvent, temperature, and other conditions depending on the starting compounds to be subjected to the reaction. Any solvent that does not adversely affect the reaction can be used, and a suitable example is N,N-dimethylformamide. The reaction can be carried out in the presence of a suitable base. A suitable example is N,N-diisopropylethylamine. The reaction can be carried out in the presence of a suitable condensing agent. A suitable example is 1-(bis(dimethylamino)methylene)-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxide hexafluorophosphate. The reaction can be carried out at room temperature or by heating. 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. The starting compounds used in each production method may be known compounds, or compounds obtained by starting from known compounds and then using the methods described in the various Examples in the Examples section below. For production methods other than the above-mentioned (Production Method 1) and (Production Method 2), reference may be made to the production methods described in the various Examples in the Examples section below.

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

[0153] (Regarding 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, hepatic fibrosis, fatty liver, metabolic syndrome, obesity, etc.); Liver disorders (e.g., cirrhosis, acute liver failure, hereditary liver disorders, alpha-1 antitrypsin deficiency, hyperammonemia, cholestasis, etc.); immune, inflammatory, and immune-related disorders (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 disorders (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, etc.);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, melanoma, pancreatic cancer, prostate cancer, kidney cancer, etc.);

[0154] (Regarding Modes 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 either 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) (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 this 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 suppressing 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 this 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, carboxymethylcellulose calcium, 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, etc.), and soothing agents (e.g., benzyl alcohol, etc.).

[0160] If necessary, formulation additives such as preservatives (e.g., paraoxybenzoic 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 may 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 may vary depending on the dosage form, administration method, carrier, etc. The pharmaceutical compositions may be prepared by conventional methods in the field of formulation technology depending on the form. The pharmaceutical compositions may also be formed into sustained-release preparations containing the active ingredient.

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

[0163] (Regarding Administration Route) Compound (I) of the present application may be administered alone or as a pharmaceutical composition orally or parenterally (e.g., intravenously, intramuscularly, subcutaneously, intraorganly, intranasally, intradermally, by instillation, intracerebral, intrarectally, intravaginally, intraperitoneally, and into a lesion).

[0164] 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 is 1 to 250 mg of Compound (I) per administration when administered orally, and 0.1 to 1000 mg when administered parenterally.

[0165] (Use as a prodrug) Compound (I) can be used in the form of a prodrug. Use in the form of such a prodrug is also included 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 or succinylated, etc.]. Examples of suitable prodrugs include 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, prodrugs of compound (I) may be those that are converted to compound (I) under physiological conditions, as described in "Drug Development," Vol. 7, Molecular Design, pp. 163-198, Hirokawa Shoten, 1990. The prodrugs 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 an isotope (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 (PET tracer) used in positron emission tomography (PET), and can be useful in fields such as medical diagnosis. １ H ２ Compound (I) also encompasses deuterium conversion products converted to H(D). Tautomers are also encompassed by compound (I). Compound (I) may be a pharmaceutically acceptable co-crystal or co-crystal salt. Here, a co-crystal or a co-crystal salt refers to a crystalline substance composed of two or more unique solids at room temperature, each having different physical properties (e.g., structure, melting point, heat of fusion, hygroscopicity, solubility, stability, etc.). A co-crystal or a co-crystal salt can be produced by a co-crystallization method known per se.

[0167] (Regarding Combination with Other Drugs) Compound (I) of the present application may be used in combination with other active ingredients (hereinafter abbreviated as concomitant drugs). As concomitant drugs, compounds or salts thereof that may have preventive and / or therapeutic effects may be appropriately blended depending on the disease to be prevented or treated. By combining compound (I) of the present application with concomitant drugs, excellent effects can be obtained, such as: (1) the dosage can be reduced compared to when compound (I) of the present application or concomitant drugs are administered alone; (2) the drug to be used in combination with compound (I) of the present application can be selected depending on the patient's symptoms (mild, severe, etc.); (3) the treatment period can be extended by selecting a concomitant drug with a different mechanism of action from compound (I) of the present application; (4) the therapeutic effect can be sustained by selecting a concomitant drug with a different mechanism of action from compound (I) of the present application; and (5) a synergistic effect can be obtained by combining compound (I) of the present application with concomitant drugs.

[0168] Hereinafter, the combined use of compound (I) of the present application and a concomitant drug is referred to as "the present combination drug." When using the present combination drug, the administration timing of compound (I) of the present application and the concomitant drug is not limited, and compound (I) of the present application or a pharmaceutical composition thereof and the concomitant drug or a pharmaceutical composition thereof may be administered to a subject simultaneously or at staggered times. The dose of the concomitant drug may be similar to 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 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 compound (I) of the present application and a concomitant drug, (2) simultaneous administration of two preparations obtained by separately formulating compound (I) of the present application and a concomitant drug via the same administration route, (3) administration of two preparations obtained by separately formulating compound (I) of the present application and a concomitant drug via the same administration route with a time lag, (4) simultaneous administration of two preparations obtained by separately formulating compound (I) of the present application and a concomitant drug via different administration routes, and (5) administration of two preparations obtained by separately formulating compound (I) of the present application and a concomitant drug via different administration routes with a time lag (e.g., administration of compound (I) of the present application followed by the concomitant drug, or administration in the reverse order), etc. The blending ratio of compound (I) of the present application 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 Compound (I) of the present application in the combination agent varies depending on 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 formulation. The content of the concomitant drug in the combination agent varies depending on 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 formulation. The content of additives such as carriers in the combination agent varies depending on the formulation, but is usually about 1 to 99.99% by weight, preferably about 10 to 90% by weight, based on the total formulation. Furthermore, similar contents may be used when Compound (I) of the present application and the concomitant drug are formulated separately.

[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 at 0°C under a nitrogen atmosphere, 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. Thereafter, water 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:methanol=5:15:2), and the solvent was removed under reduced pressure to yield 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 stirred for 30 minutes. 0.054 g of 4-phenylbutyl bromide and 0.019 g of potassium iodide were then added and stirred for 19 hours at room temperature. Water was then added, and the mixture was separated using hexane:ethyl acetate=1:1. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to give a crude product, which was purified by preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was evaporated under reduced pressure to give 0.022 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 Methyl 3-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoate (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) were added 1.5 mL of triethylamine and 5.31 g of 3-(methoxycarbonyl)-1-iodobenzene at room temperature under a nitrogen atmosphere, and the mixture was stirred at 50°C for 24 hours. Thereafter, the mixture was filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with 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 yield 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 evaporated under reduced pressure to yield a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to yield 3.56 g of methyl 3-(4-bromobut-1-yn-1-yl)benzoate. (3) To 3.60 g of methyl 3-(4-bromobut-1-yn-1-yl)benzoate, 2.27 g of palladium fibroin was added under a nitrogen atmosphere, followed by 40 mL of methanol. The mixture was stirred at room temperature under a hydrogen atmosphere for 24 hours. The crude product was then filtered through Celite, and the resulting mixture was purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to yield 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 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 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 0.023 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, 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 preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed 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 was added 0.010 g of sodium hydride (60%, dispersed in liquid paraffin) 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 then evaporated 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 0.016 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 dimethylsulfide 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 (dr 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. Further, 0.021 g of crude (3-phenylcyclobutyl)methyl methanesulfonate was added, 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, dried over anhydrous sodium sulfate, and the solvent was 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 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 with 7 mL of triethylamine and 0.250 g of 3-butyn-1-ol at room temperature under a nitrogen atmosphere, and the mixture was 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, 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 0.610 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 removed under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1). The solvent was then removed under reduced pressure to obtain 0.844 g of 3-(4-bromobut-1-yn-1-yl)benzonitrile. (3) To 0.440 g of 3-(4-bromobut-1-yn-1-yl)benzonitrile, 0.158 g of palladium fibroin was added under a nitrogen atmosphere, followed by the addition of 4 mL of ethanol, and the mixture was stirred at room temperature for 26 hours under a hydrogen atmosphere. The crude product was then 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.Further, 0.041 g of 3-(4-bromobutyl)benzonitrile and 0.007 g of potassium iodide were added, and the mixture was stirred at room temperature for 17 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 (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 was added 2.795 mL of diethylzinc (1 mol / L toluene solution) 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 under a nitrogen atmosphere at 0°C. After stirring at 0°C for 30 minutes, the mixture was added dropwise to the original flask and stirred at room temperature for 23 hours. Saturated aqueous ammonium chloride solution 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 yield 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 yield 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 was added 0.697 g of sulfuryl chloride under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 3 hours. Saturated aqueous sodium bicarbonate 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=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. Then, saturated aqueous potassium sodium tartrate was 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 0.057 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. Further, 0.044 g of crude (3-phenylcyclopentyl)methyl methanesulfonate was 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 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 0.009 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 with 20 mL of triethylamine and 2.12 g of 1-chloro-2-iodobenzene at room temperature under a nitrogen atmosphere, and the mixture was 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, 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: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 stirred at room temperature for 3 hours. The solvent was then removed under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to obtain 1.87 g of 1-(4-bromobut-1-yn-1-yl)-2-chlorobenzene. (3) To 0.200 g of 1-(4-bromobut-1-yn-1-yl)-2-chlorobenzene, 0.069 g of palladium fibroin was added under a nitrogen atmosphere, followed by the addition of 10 mL of methanol. The mixture was stirred at room temperature for 24 hours under a hydrogen atmosphere. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was removed under reduced pressure to give 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, 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 0.005 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 iodide (I), and 0.297 g of tetrakis(triphenylphosphine)palladium (0) were added with 30 mL of triethylamine and 3.80 g of 1-fluoro-2-iodobenzene at room temperature under a nitrogen atmosphere, and the mixture was stirred at 50 ° C. for 24 hours. Thereafter, the mixture was 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 distilled off 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 removed under reduced pressure to yield 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 solvent was then removed under reduced pressure to yield a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to yield 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 30 mL of methanol. The mixture was stirred at room temperature under a hydrogen atmosphere for 46 hours. The crude product was then filtered through Celite, and the resulting mixture was 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) 0.020 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone was dissolved in 3 mL of N,N-dimethylformamide under a nitrogen atmosphere at room temperature. 0.005 g of sodium hydride (60%, dispersed in liquid paraffin) was added and the mixture was stirred at room temperature for 30 minutes.Further, 0.040 g of 1-(4-bromobutyl)-2-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 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 0.006 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 the mixture was stirred at 50 ° C. for 3 hours. Thereafter, the mixture was 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 solvent was then removed under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), after which the solvent was removed under reduced pressure to obtain 2.45 g of 1-(4-bromobut-1-yn-yl)-3-fluorobenzene. (3) To 1.00 g of 1-(4-bromobut-1-yn-yl)-3-fluorobenzene, 0.740 g of palladium fibroin was added under a nitrogen atmosphere, followed by the addition of 30 mL of methanol, and the mixture was stirred at room temperature for 46 hours under a hydrogen atmosphere. The crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1) and the solvent was removed under reduced pressure to give 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 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 0.014 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 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. Further, 0.09 g of crude 6-methylheptane methanesulfonate was 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 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 0.032 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. Saturated aqueous potassium sodium tartrate 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 0.06 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 evaporated under reduced pressure to obtain 0.052 g of crude (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. Further, 0.058 g of crude (trans-4-phenylcyclohexyl)methyl methanesulfonate was added, and the mixture was stirred at room temperature for 16 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 distilled off 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, 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 preparative thin-layer chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed 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) 3-butyn-1-ol 1.00 g, copper(I) iodide 0.082 g, tetrakis(triphenylphosphine)palladium(0) 0.247 g, triethylamine 30 mL, 1-fluoro-4-iodobenzene 3.17 g were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at 50 ° C. for 27 hours. Thereafter, the mixture was 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 distilled off 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 removed under reduced pressure to yield 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 removed under reduced pressure to yield a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate:methanol=5:5:1), and the solvent was removed under reduced pressure to yield 1.87 g of 1-(4-bromobut-1-yn-1-yl)-4-fluorobenzene. (3) 0.666 g of palladium fibroin was added to 0.900 g of 1-(4-bromobut-1-yn-1-yl)-4-fluorobenzene under a nitrogen atmosphere, followed by 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 0.910 g of 1-(4-bromobutyl)-4-fluorobenzene. (4) 0.025 g of (morpholin-4-yl)(1H-pyrrolo[3,2-b]pyridin-3-yl)methanone was added to 3 mL of N,N-dimethylformamide under a nitrogen atmosphere at room temperature, and 0.006 g of sodium hydride (60%, dispersed in liquid paraffin) was added and stirred at room temperature for 30 minutes.Further, 0.050 g of 1-(4-bromobutyl)-4-fluorobenzene and 0.009 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 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 the mixture was 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, 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 0.520 g of 4-(3-chlorophenyl)-3-butyn-1-ol. (2) 0.234 g of palladium fibroin was added to 0.504 g of 4-(3-chlorophenyl)-3-butyn-1-ol under a nitrogen atmosphere, followed by the addition of 10 mL of methanol and stirring under a hydrogen atmosphere at room temperature for 24 hours. 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 0.489 g of 1-(4-hydroxybutyl)-3-chlorobenzene. (3) 0.113 g of methanesulfonic anhydride, 0.188 mL of triethylamine, and 0.007 g of 4-dimethylaminopyridine were added to a solution of 0.100 g of 1-(4-hydroxybutyl)-3-chlorobenzene in 5 mL of dichloromethane 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 give 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.Further, 0.051 g of crude 4-(3-chlorophenyl)butyl methanesulfonate and 0.016 g of potassium iodide were added, and the mixture was stirred at room temperature for 20 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 0.052 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 with 20 mL of triethylamine and 1.34 g of 2-iodoanisole at room temperature under a nitrogen atmosphere, and the mixture was 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, 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 0.625 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 under a hydrogen atmosphere at room temperature for 24 hours. 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 0.460 g of 4-(2-methoxyphenyl)butan-1-ol. (3) 0.116 g of methanesulfonic anhydride, 0.192 mL of triethylamine, and 0.007 g of 4-dimethylaminopyridine were added to a solution of 0.100 g of 4-(2-methoxyphenyl)butan-1-ol in 3 mL of dichloromethane 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 give 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 at room temperature under a nitrogen atmosphere, and the mixture was stirred at room temperature for 30 minutes.Further, 0.051 g of crude 4-(2-methoxyphenyl)butyl methanesulfonate and 0.017 g of potassium iodide were added, and the mixture was stirred at room temperature for 20 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 0.050 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) To 0.400 g of 3-butyn-1-ol, 0.054 g of copper(I) iodide, and 0.200 g of dichlorobis(triphenylphosphine)palladium(II), 20 mL of triethylamine and 1.34 g of 3-iodoanisole were added under a nitrogen atmosphere at room temperature, and the mixture was 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, 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 0.625 g of 4-(3-methoxyphenyl)-3-butyn-1-ol. (2) 0.993 g of palladium fibroin was added to 0.625 g of 4-(3-methoxyphenyl)-3-butyn-1-ol 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, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to yield 0.505 g of 1-(4-hydroxybutyl)-3-methoxybenzene. (3) 0.116 g of methanesulfonic anhydride, 0.192 mL of triethylamine, and 0.007 g of 4-dimethylaminopyridine were added to a solution of 0.100 g of 1-(4-hydroxybutyl)-3-methoxybenzene in 3 mL of dichloromethane 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 give 0.080 g of crude 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.Further, 0.051 g of crude 4-(3-methoxyphenyl)butyl methanesulfonate and 0.017 g of potassium iodide were 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 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 0.049 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) To 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 20 mL of triethylamine and 1.34 g of 4-iodoanisole under a nitrogen atmosphere at room temperature, and the mixture was 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, 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 0.158 g of 4-(4-methoxyphenyl)-3-butyn-1-ol. (2) 0.075 g of palladium fibroin was added to 0.158 g of 4-(4-methoxyphenyl)-3-butyn-1-ol under a nitrogen atmosphere, followed by the addition of 10 mL of methanol and stirring under a hydrogen atmosphere at room temperature for 48 hours. 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 yield 0.138 g of 1-(4-hydroxybutyl)-4-methoxybenzene. (3) 0.116 g of methanesulfonic anhydride, 0.192 mL of triethylamine, and 0.007 g of 4-dimethylaminopyridine were added to a solution of 0.100 g of 1-(4-hydroxybutyl)-4-methoxybenzene in 10 mL of dichloromethane 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 give 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.Further, 0.050 g of crude 4-(4-methoxyphenyl)butyl methanesulfonate and 0.016 g of potassium iodide were 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 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 0.054 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 was added 0.051 g of sodium hydride (60%, dispersed in liquid paraffin) under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature 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 hexane:ethyl acetate solution. 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=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, 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 0.196 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 distilled off under reduced pressure to obtain 0.221 g of a crude product of 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 the mixture was stirred at room temperature for 6 hours to prepare a Grignard reagent. Subsequently, the prepared 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 the mixture was stirred at room temperature for 16 hours. Thereafter, a saturated aqueous solution of ammonium chloride was added, and the mixture was separated with 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 yield 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, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to yield the 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 0.152 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 the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The mixture was then filtered through Celite, and 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 0.108 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, and dried over anhydrous sodium sulfate. The solvent was then 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 the mixture was stirred at room temperature for 6 hours to prepare a Grignard reagent. Subsequently, the prepared 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 the mixture was stirred at room temperature for 16 hours. Thereafter, a saturated aqueous solution of ammonium chloride was added, and the mixture was separated with 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 yield 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, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to yield the 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 give 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. 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), and the solvent was evaporated under reduced pressure to give 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 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 0.015 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) To 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 20 mL of triethylamine and 2.63 g of 4-iodoacetophenone at room temperature under a nitrogen atmosphere, and the mixture was stirred at 50°C for 19 hours. Thereafter, the mixture was filtered through Celite, neutralized with a saturated aqueous ammonium chloride solution, and separated with 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 distilled off under reduced pressure to obtain 1.25 g of 1-(4-(4-hydroxy-1-butyn-1-yl)phenyl)ethan-1-one. (2) To 1.25 g of 1-(4-(4-hydroxybut-1-yn-1-yl)phenyl)ethan-1-one, 0.558 g of palladium-fibroin was added under a nitrogen atmosphere, followed by addition of 30 mL of methanol and stirring under a hydrogen atmosphere at room temperature for 48 hours. The resulting crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was distilled off 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) To 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 30 mL of triethylamine and 2.63 g of 3-iodoacetophenone at room temperature under a nitrogen atmosphere, and the mixture was stirred at 50°C for 19 hours. Thereafter, the mixture was filtered through Celite, neutralized with a saturated aqueous ammonium chloride solution, and separated with 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 distilled off 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 addition of 30 mL of methanol and stirring under a hydrogen atmosphere at room temperature for 30 hours. The resulting crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was distilled off 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 Methyl 2-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoate (1) To 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 20 mL of triethylamine and 5.31 g of 2-(methoxycarbonyl)-1-iodobenzene at room temperature under a nitrogen atmosphere, and the mixture was 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, 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 yield 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 evaporated under reduced pressure to yield a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to yield 4.03 g of methyl 2-(4-bromobut-1-yn-1-yl)benzoate. (3) To 3.30 g of methyl 2-(4-bromobut-1-yn-1-yl)benzoate, 2.08 g of palladium fibroin was added under a nitrogen atmosphere, followed by 10 mL of methanol. The mixture was stirred at room temperature under a hydrogen atmosphere for 48 hours. The crude product was then filtered through Celite, and the resulting mixture was purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to yield 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 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 0.010 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 Methyl 4-(4-(3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)butyl)benzoate (1) To 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 30 mL of triethylamine and 3.54 g of 4-(methoxycarbonyl)-1-iodobenzene at room temperature under a nitrogen atmosphere, and the mixture was 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, 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 yield 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 evaporated under reduced pressure to yield a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was evaporated under reduced pressure to yield 1.72 g of methyl 4-(4-bromobut-1-yn-1-yl)benzoate. (3) To 1.25 g of methyl 4-(4-bromobut-1-yn-1-yl)benzoate, 0.786 g of palladium fibroin was added under a nitrogen atmosphere, followed by 30 mL of methanol. The mixture was stirred at room temperature for 19 hours under a hydrogen atmosphere. The crude product was then filtered through Celite, and the resulting mixture was purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to yield 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 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 0.010 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 was added 0.811 g of Dess-Martin periodinane under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 1.5 hours. Saturated aqueous sodium thiosulfate 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 0.223 g of 2-phenylcyclopropane-1-carboxaldehyde (dr 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, 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 yield 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 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 yield 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-(morpholin-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, 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 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 under a nitrogen atmosphere at 0°C, 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, followed by the addition of 4 mL of ethanol, and the mixture was stirred at room temperature under a hydrogen atmosphere for 18 hours. The mixture was then filtered through Celite, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), after which the solvent was 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 under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1). The solvent was then removed under reduced pressure to yield 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. Further, 0.052 g of ((3-(bromomethyl)cyclobutyl)oxy)benzene and 0.018 g of potassium iodide were 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 hexane:ethyl acetate solution. The resulting organic layer was separated, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was then removed under reduced pressure to yield 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. Thereafter, a 5% aqueous potassium hydrogen sulfate solution was added, and the mixture was separated with 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 obtained crude product was purified by silica gel chromatography (methanol:ethyl acetate=5:1), and then the solvent was distilled off 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 hexane:ethyl acetate=1:1. 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. Thereafter, water was added, and the mixture was separated using hexane:ethyl acetate=1:1. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give a crude product. The crude product was purified by preparative thin-layer chromatography (hexane:ethyl acetate=1:1), and the solvent was removed under reduced pressure to give 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) To 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 30 mL of triethylamine and 4.21 g of 3-(methoxycarbonyl)-1-iodobenzene at room temperature under a nitrogen atmosphere, and the mixture was stirred at 50°C for 6 hours. Thereafter, the mixture was filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with 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 yield 2.76 g of methyl 3-(3-hydroxyprop-1-yn-1-yl)benzoate. (2) To 2.00 g of methyl 3-(3-hydroxyprop-1-yn-1-yl)benzoate, 0.883 g of palladium fibroin was added under a nitrogen atmosphere, followed by 40 mL of methanol and stirring at room temperature for 42 hours under a hydrogen atmosphere. The resulting crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to yield 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 removed under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure, yielding 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.Further, 0.778 g of methyl 3-(3-bromopropyl)benzoate was added, and the mixture was stirred at room temperature for 17 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 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 0.232 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 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, 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=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 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=1:5), 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. Thereafter, a saturated aqueous ammonium chloride solution was added, and the mixture was separated with ethyl acetate. The obtained 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:methanol=5:5:1), and the solvent was removed 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. Thereafter, a saturated aqueous ammonium chloride solution was added, and the mixture was separated with ethyl acetate. The obtained 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:methanol=5:5:1), and the solvent was then distilled off 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. Thereafter, a 5% aqueous solution of potassium hydrogen sulfate was added, and the mixture was separated with 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 removed under reduced pressure to give 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. The solvent was then distilled off under reduced pressure to give a crude product, which was purified by preparative thin-layer chromatography (methanol:ethyl acetate=1:9), and the solvent was then distilled off under reduced pressure to give 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. 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 were added 1.155 g of carbon tetrabromide and 0.99 g of triphenylphosphine under a nitrogen atmosphere at 0°C, and the mixture was stirred at room temperature for 16 hours. The solvent was then evaporated under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1). The solvent was then evaporated under reduced pressure to give 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 hexane:ethyl acetate solution. 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 then 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 at room temperature under a nitrogen atmosphere, and the mixture was stirred at room temperature for 1 hour. Thereafter, a 5% aqueous solution of potassium hydrogen sulfate was added, and the mixture was separated using ethyl acetate.The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give a crude product. The 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 0.106 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 hexane:ethyl acetate=1:1. 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. Thereafter, water was added, and the mixture was separated using hexane:ethyl acetate=1:1. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give a crude product. The crude product was purified by silica gel chromatography (ethyl acetate:methanol=9:1), and the solvent was removed under reduced pressure to give 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. The solvent was then distilled off under reduced pressure, and the mixture was purified by recrystallization (hexane-diethyl ether). The solvent was then distilled off under reduced pressure to give 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 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) 0.027 g of palladium-carbon was added to 0.125 g of 4-(4-(benzyloxy)but-1-en-1-yl)oxane under a nitrogen atmosphere, followed by the addition of 2 mL of ethanol. The mixture was stirred at room temperature under a hydrogen atmosphere for 22 hours. The crude product was then purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was removed under reduced pressure to give 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 solvent was then removed under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure to yield 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 for 15 minutes at room temperature. 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 hexane:ethyl acetate solution. The resulting organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to yield 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) To 1.14 g of 2-propyn-1-ol, 0.039 g of copper(I) iodide, and 0.234 g of tetrakis(triphenylphosphine)palladium(0), 30 mL of triethylamine and 5.31 g of 4-(methoxycarbonyl)-1-iodobenzene were added under a nitrogen atmosphere at room temperature, and the mixture was stirred at 50°C for 4 hours. Thereafter, the mixture was filtered through Celite, neutralized with saturated aqueous ammonium chloride, and separated with 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 yield 3.60 g of methyl 4-(3-hydroxyprop-1-yn-1-yl)benzoate. (2) To 2.00 g of methyl 4-(3-hydroxyprop-1-yn-1-yl)benzoate, 0.883 g of palladium fibroin was added under a nitrogen atmosphere, followed by 40 mL of methanol and stirring at room temperature for 48 hours under a hydrogen atmosphere. The resulting crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate = 1:1), and the solvent was evaporated under reduced pressure to yield 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 under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure, yielding 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.Further, 0.364 g of methyl 4-(3-bromopropyl)benzoate was 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-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)propyl)benzoate. (5) To a 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 then the solvent was 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, 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 0.483 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, and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. After that, the mixture was filtered through Celite to obtain 0.311 g of crude 4-(3-(5-methyl-1,3,4-oxadiazol-2-yl)phenyl)butan-1-ol.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 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 (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) To 0.5 g of trans-4-hydroxycyclohexane-1-carboxylic acid, 5.2 mL of an ethanol-concentrated sulfuric acid mixed solution was added at room temperature under a nitrogen atmosphere, and the mixture was stirred under reflux for 19 hours. Saturated aqueous sodium bicarbonate 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=1:1), and the solvent was evaporated 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 hexane:ethyl acetate = 1:1. 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. 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 0.077 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 solvent was then removed under reduced pressure to give a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=9:1). The solvent was then removed under reduced pressure to give 0.096 g of ((trans-4-(bromomethyl)cyclohexyl)oxy)benzene.(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 hexane:ethyl acetate = 1:1. 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 was added 0.892 g of p-toluenesulfonyl chloride 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 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 0.849 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 resulting crude product was purified by silica gel chromatography (ethyl acetate:methanol=9:1), and the solvent was evaporated under reduced pressure to give 0.435 g of 4-((3-(morpholine-4-carbonyl)-1H-pyrrolo[3,2-b]pyridin-1-yl)methyl)cyclohexane-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)cyclohexane-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 with 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 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 give 0.019 g (dr 1:0.7) of (1-((4-hydroxy-4-phenylcyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 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 under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. 0.963 g of tert-butyldimethylchlorosilane was 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, 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 and ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to obtain 1.215 g of methyl trans-4-(((tert-butyldimethylsilyl)oxy)methyl)cyclohexanecarboxylate. (2) To a mixed 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 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 resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate (4:1)), and the solvent was evaporated 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 resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to obtain 0.987 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 at 0°C under a nitrogen atmosphere, 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 the crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and the solvent was then distilled off 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 under reduced pressure, and the resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 1:1). The solvent was then removed under reduced pressure, yielding 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 under a nitrogen atmosphere at room temperature, and the mixture was stirred at room temperature for 30 minutes. Further, 0.68 g of (trans-4-(bromomethyl)cyclohexyl)(phenyl)methanone was added, and the mixture was stirred at room temperature for 16 hours. Water was then added, and the mixture was separated using hexane:ethyl acetate=1:1. The obtained 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 (ethyl acetate:methanol=9:1), and the solvent was evaporated 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 with 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 obtained crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=5:1), and the solvent was then distilled off under reduced pressure to give 0.093 g (dr 1:0.1) of (1-((4-(hydroxy(phenyl)methyl)cyclohexyl)methyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)(morpholino)methanone. 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 were added 8.583 mL of triethylamine, 8.446 g of di-tert-butyl dicarbonate, and 0.095 g of 4-dimethylaminopyridine 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 then distilled off under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate=1:1), and then the solvent was distilled off 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 distilled off 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 yield 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 evaporated under reduced pressure to yield a crude product, which was then purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to yield 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, and dried over anhydrous sodium sulfate. The solvent was then evaporated under reduced pressure to obtain the crude product. The resulting crude product was purified by silica gel chromatography (ethyl acetate:methanol=9:1), and the solvent was removed under reduced pressure to give 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 at 0°C under a nitrogen atmosphere, and the mixture was stirred at room temperature for 3 hours. The solvent was then removed under reduced pressure, and the mixture 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 with ethyl acetate. 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 a crude product.The obtained crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=9:1), and then the solvent was distilled off 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 at room temperature under a nitrogen atmosphere, and the mixture was stirred at room temperature for 17 hours. Water was then added, and the mixture was separated with 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 obtained crude product was purified by preparative thin-layer chromatography (ethyl acetate:methanol=9:1), and then the solvent was distilled off 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 was added 4.886 g of Dess-Martin periodinane at 0°C under a nitrogen atmosphere, and the mixture was stirred at room temperature for 5 hours. Saturated aqueous sodium thiosulfate 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=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 resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 4:1), and the solvent was evaporated under reduced pressure to yield 0.245 g (1,1'-bi(cyclohexane))-4-carboxaldehyde (1:0.3). (3) To a solution of 0.4 g of (1,1'-bi(cyclohexane))-4-carboxaldehyde (4 mL) in 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, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to yield the 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 yield 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 evaporated under reduced pressure to yield a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=9:1), and the solvent was evaporated under reduced pressure to yield 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 was added 0.122 g of sodium hydride (60%, dispersed in liquid paraffin) under a nitrogen atmosphere at 0°C, and the mixture was stirred at 0°C for 30 minutes. Further, 0.5 g of (1,1'-bi(cyclohexane))-4-one was added, and the mixture was stirred at room temperature for 24 hours. Thereafter, a saturated aqueous solution of ammonium chloride was added, and the mixture was separated with 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 yield 0.385 g of ethyl ((1,1'-bi(cyclohexane))-4-ylidene)acetate. (2) To 0.38 g of ethyl ((1,1'-bi(cyclohexane))-4-ylidene)acetate, 0.213 g of palladium-fibroin was added under a nitrogen atmosphere, followed by 4 mL of ethyl acetate. The mixture was stirred at room temperature for 24 hours under a hydrogen atmosphere. The resulting crude product was then filtered through Celite, and purified by silica gel chromatography (hexane:ethyl acetate=4:1), and the solvent was evaporated under reduced pressure to yield 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 solvent was then removed by distillation under reduced pressure to obtain a crude product, which was purified by silica gel chromatography (hexane:ethyl acetate=4:1). The solvent was then removed by distillation 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 was added 0.149 g of sodium hydride (60%, dispersed in liquid paraffin) at 0°C under a nitrogen atmosphere, and the mixture was 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, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to obtain a crude product. The resulting crude product was purified by silica gel chromatography (hexane:ethyl acetate = 7:3), and the solvent was removed under reduced pressure to yield 0.965 g of 6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxaldehyde. (2) To a solution of 0.965 g of 6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxaldehyde in 21 mL of tert-butanol, 7 mL of tetrahydrofuran, and 3.5 mL of 2-methyl-2-butene, a solution of 3.24 g of anhydrous sodium dihydrogen phosphate in 5.5 mL of water was slowly added dropwise at room temperature under a nitrogen atmosphere. A solution of 3.24 g of sodium chlorite in 5.5 mL of water was then slowly added dropwise and stirred at room temperature for 45 minutes. Saturated saline was then added, and the mixture was separated using ethyl acetate. The resulting organic layer was separated and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to obtain 1.07 g of 6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid.(3) To a solution of 1.01 g of 6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridine-3-carboxylic acid in 30 mL of N,N-dimethylformamide, 0.283 g of morpholine, 0.760 mL of N,N-diisopropylethylamine, and 1.23 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 40 minutes. Water was then added, and the mixture was separated using a 1:4 mixture of hexane and ethyl acetate. The resulting organic layer was washed with water, 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 1.18 g of morpholino(6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.54 (d, J = 2.0 Hz, 1H), 7.76 (s, 1H), 7.75 (d, J = 2.0 Hz, 1H), 7.29 (t, J = 7.2 Hz, 2H), 7.22-7.21 (m, 1H), 7.15-7.13 (m, 2H), 4.07 (t, J = 7.2 Hz, 2H), 3.78 (s, 8H), 2.66 (t, J = 7.6 Hz, 2H), 1.91-1.87 (m, 2H), 1.70-1.66 (m, 2H).

[0225] Example 56 Morpholino(6-amino-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone A mixture of 0.049 g of tris(dibenzylideneacetone)dipalladium(0), 0.066 g of (±)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 0.071 g of sodium tert-butoxide, 0.235 g of morpholino(6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone, 0.153 g of benzophenone imine, and 3 mL of toluene was stirred at 90°C for 19 hours under a nitrogen atmosphere. Thereafter, the mixture was filtered through Celite, and the filtrate was evaporated under reduced pressure. The resulting residue was dissolved in 20 mL of tetrahydrofuran, and 2 mL of 3 mol / L hydrochloric acid was slowly added dropwise. The mixture was stirred at room temperature for 1 hour under a nitrogen atmosphere. The reaction solution was then neutralized with saturated aqueous sodium bicarbonate and separated with ethyl acetate. The resulting organic layer was separated 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 (ethyl acetate:methanol = 9:1), and the solvent was evaporated under reduced pressure to obtain 0.18 g of morpholino(6-amino-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. 1H-NMR (400 MHz, CHLOROFORM-D) δ 8.09-8.08 (m, 1H), 7.57-7.56 (m, 1H), 7.30-7.28 (m, 2H), 7.22-7.18 (m, 1H), 7.15-7.13 (m, 2H), 6.83-6.82 (m, 1H), 4.01-3.97 (m, 2H), 3.73 (m, 10H), 2.64 (t, J = 7.6 Hz, 2H), 1.89-1.82 (m, 2H), 1.71-1.63 (m, 2H)

[0226] Example 57 Morpholino(6-hydroxy-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone (1) 0.002 g of palladium(II) acetate, 0.071 g of potassium acetate, 0.107 g of morpholino(6-bromo-1-(4-phenylbutyl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone, 0.074 g of bis(pinacolato)diboron, and 3 mL of N,N-dimethylformamide were added sequentially, and the mixture was stirred at 85° C. for 19 hours under a nitrogen atmosphere. Thereafter, water was added to the reaction solution, and the mixture was separated using ethyl acetate. The resulting organic layer was separated, washed with water and saturated brine, dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure to yield 0.117 g of crude morpholino(1-(4-phenylbutyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone. (2) 0.117 g of crude morpholino(1-(4-phenylbutyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[3,2-b]pyridin-3-yl)methanone was dissolved in 3 mL of tetrahydrofuran and 3 mL of water, and 0.095 g of sodium perborate tetrahydrate was added at room temperature under a nitrogen atmosphere. The mixture was stirred at room temperature for 20 hours. Saturated aqueous ammonium chloride was then added, and the mixture was separated using ethyl acetate. The organic layer was separated, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure to give a crude product, which was purified by preparative thin-layer chromatography (chloroform:methanol=1:19), and the solvent was removed un...

Claims

1. A compound of the following formula (I): [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): (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 join together to form a heterocycloalkane or a cycloalkane together with the carbon atom to which they are attached; 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 １ and R ２ each independently represents an optionally substituted C 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 an integer of 0 to 3; 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 substituted or unsubstituted divalent hydrocarbon ring group, a fused aromatic heterocyclic group, or a heterocycloalkylene group; g represents 0 or 1; Q represents 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 M may be substituted with an alkyl group; １ is an optionally substituted C １－４ represents an alkylene group; 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 are 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 (1) M represents an alkyl group, or an aryl group which may be substituted. 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): (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 Rz is a hydrogen atom or an optionally substituted C １－６ 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 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 an integer of 0 to 3; ３ａ is a hydrogen atom or C １－６ A represents 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; 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 R represents an alkyl group; 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 2. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein: R is an aryl group.

3. R １ and R ２ together with the nitrogen atom to which they are attached, form the following formulae (IIa) to (IIe): (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 Rz may form a cycloalkane; １－６ 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 C １－６ C optionally substituted with an alkoxy group １－６ 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 an integer of 0 to 3; ３ａ is a hydrogen atom or C １－６ A represents 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; 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 M may be substituted with an alkyl group; 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 2. The compound of claim 1, or a pharmaceutically acceptable salt thereof, wherein: R is an aryl group.

4. (1) 1) g indicates 1; 2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; 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 )-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q represents 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 may have 1 to 3 R ４ (where R ４ is optionally substituted with (as defined in claim 1); or (2) 1) g represents 0; 2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; 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 is optionally substituted with as defined in claim 1 ; or (iii) M １ But -(CH ２ )-, 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 R may be substituted with an alkyl group; 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 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 2. The compound according to claim 1, or a pharmaceutically acceptable salt thereof, wherein R represents an alkyl group, an optionally substituted aryl group, or an optionally substituted aryl group.

5. R １ and R ２ together with the nitrogen atom to which they are attached form the following formula (IIa): (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 The compound according to any one of claims 1 to 4, or a pharmaceutically acceptable salt thereof, wherein n1 represents an integer of 0 to 3, and n2 represents an integer of 0 to 3, and n3 represents an integer of 0 to 3, and n4 represents an integer of 0 to 3, and n5 represents an integer of 0 to 3, and n6 represents an integer of 0 to 3, and n7 represents an integer of 0 to 3, and n8 represents an integer of 0 to 3, and 6. (1) g denotes 1; (2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; 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 )-, A represents an optionally substituted divalent aromatic hydrocarbon ring group, and Q represents 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 may have 1 to 3 R ４ (where R ４ is optionally substituted with as defined in claim 1; A compound according to claim 1 or 4, or a pharmaceutically acceptable salt thereof.

7. g is 1; f R ３ are each independently -OR ｃ１ (R ｃ１ is as described below); f represents an integer of 0 to 3; R ３ａ is a hydrogen atom or C １－６ A represents an alkyl group; ３－８ Cycloalkylene group, C ３－８ Cycloalkenylene group, C ６－１４ Q is an arylene group, a divalent 8- to 14-membered fused aromatic heterocyclic group, or a 3- to 8-membered heterocycloalkylene group; 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 substituted with 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 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 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 5. The compound according to claim 1, wherein R is an alkyl group, 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):

8. The compound according to claim 7, or a pharmaceutically acceptable salt thereof, which forms a group represented by the formula: (wherein n1 represents 0).

9. (1) g indicates 0; (2) (i) M １ is optionally substituted C ２－４ (ii) M represents an alkylene group; 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 is optionally substituted with as defined in claim 1 ; or (iii) M １ But -(CH ２ )-, 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 R may be substituted with an alkyl group; 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 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 5. The compound according to claim 1 or 4, or a pharmaceutically acceptable salt thereof, wherein:

10. g is 0; f R ３ But, -OR ｃ１ (R ｃ１ is as defined below); f is an integer of 0 to 3; Q is C １－６ Alkyl group, C ３－１４ Cycloalkyl group, C ６－１４ aryl group or 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), 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 M may be substituted with an alkyl group; １ But C １－６ C optionally substituted with an alkyl group １－４ represents an alkylene group; 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): The compound according to claim 10 or a pharmaceutically acceptable salt thereof, which forms a group represented by the formula: (wherein n1 represents 0).

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 A is an alkyl group; ３－８ Q is a cycloalkylene group; 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 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; —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 group); 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 C ３－８ heterocycloalkyl group, where R ａ３ and R ｂ３ may be joined 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 may be substituted with 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 9. The compound according to claim 8, wherein j1 to j3 each independently represent an integer of 0 to 4, 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 12. The compound according to claim 11, wherein j1 is 0, or a pharmaceutically acceptable salt thereof.

14. The compound according to any one of claims 1 to 4, or a pharmaceutically acceptable salt thereof, wherein the compound represented by formula (I) is one or more compounds selected from the group of compounds represented by the following structural formula:

15. g is 1; f is 0; R ３ａ is a hydrogen atom; ３－８ Q is a cycloalkylene group; 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 are optionally substituted with a 3- to 8-membered heterocycloalkyl group together with the nitrogen atom to which they are attached; 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 13. The compound according to claim 12, wherein j1 to j3 each independently represent an integer of 0 to 4, 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 The compound according to claim 13, wherein j1 is 0, or a pharmaceutically acceptable salt thereof.

17. A medicine containing the compound according to claim 1 or a pharmaceutically acceptable salt thereof as an active ingredient.

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 improved by an increase in autophagy function.

20. The pharmaceutical agent according to claim 17, which is an agent for preventing or treating neurodegenerative diseases; cardiovascular diseases; musculoskeletal diseases; skeletal diseases; lung diseases; kidney diseases; metabolic syndrome; liver lesions; immune, inflammatory and immune-related diseases; eye diseases; reproductive system dysfunction; congenital multisystem disorders; and / or cancer.

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