KR930019625A - Condensed Heterocyclic Ketone Derivatives, Methods for Making and Uses - Google Patents

Abstract

Since the compound of formula [I] or a salt thereof shows excellent cholinesterase inhibitory activity and monoamine reuptake inhibitory activity, it is useful as a treatment / prevention agent of senile dementia

[Wherein, Is H or an optionally substituted hydrocarbon or acyl group; Ring A is an optionally further substituted benzene ring; n is an integer from 1 to 20; Is H or an optionally substituted hydrocarbon group; May combine with adjacent nitrogen atoms to form an optionally substituted heterocyclic group; k is an integer of 0 to 3; m is an integer from 1 to 8; Provided that k is an integer greater than or equal to 2 when k = 0 and m = 2]

Description

Condensed Heterocyclic Ketone Derivatives, Methods for Making and Uses

Since this is an open matter, no full text was included.

Claims (36)

A compound of formula [I] or a pharmaceutically acceptable salt; [Wherein, Is H or an optionally substituted hydrocarbon or acyl group; Ring A is an optionally further substituted benzene ring; n is an integer of 1 to 10; Is H or an optionally substituted hydrocarbon group; May combine with adjacent nitrogen atoms to form an optionally substituted heterocyclic group; k is an integer of 0 to 3; m is an integer from 1 to 8; Provided that k is an integer greater than or equal to 2 when k = 0 and m = 2] The method of claim 1, (1) hydrogen atoms, (2) halogen, nitro, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5- to 7-membered cyclic amino, Alkyl-carbonylamino, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, Straight or branched chain which may be substituted with 1 to 5 substituents selected from the group consisting of alkylenedioxy and heterocyclic groups Alkyl, Alkylyl or Alkynyl, (3) halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclicamino, Alkyl-carbonylamino, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, May be substituted with 1 to 5 substituents selected from the group consisting of alkylenedioxy and heterocyclic groups Monocyclic cycloalkyl groups, (4) halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclicamino, Alkyl-carbonylamino, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, May be substituted with 1 to 5 substituents selected from the group consisting of alkylenedioxy and heterocyclic groups Bridged cyclic saturated hydrocarbon groups (2006.01) Alkyl, halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-cyclic cyclic amino, Alkyl-carbonylamino, Aralkyloxy, aminocarbonyloxy, mono- or di- Alkyl-substituted aminocarboxyoxy, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, Cycloalkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted amino, nitro, Phenyl, naphthyl, mono- or di-phenyl- which may be substituted with 1 to 4 substituents in the group consisting of alkyl-carbonyl and benzoyl Alkyl, phenoxy, benzoyl, phenoxycarbonyl, benzylcarbonyl, phenyl Alkyl-carbamoyl, phenylcarbamoyl, phenyl- Alkyl-carbonyl amino, benzoylamino, phenyl- Alkylsulfonyl, phenylsulfonyl, phenyl- Alkylsulfinyl, phenyl- Phenyl or naphthyl groups which may be substituted by 1 to 5 substituents selected from the group consisting of alkylsulfonylamino alkylsulfonylamino or phenylsulfonylamino groups, (6) Alkyl, halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5- to 7-membered cyclic amino, Alkyl-carbonylamino, Aralkyloxy, aminocarbonyloxy, mono- or di- Alkyl-substituted aminocarboxyoxy, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, Cycloalkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, Cycloalkyl sulfonyl, and Alkyl, Alkoxy, halogen, hydroxy, benzyloxy, amino, mono or di- Alkyl-substituted amino, nitro, Phenyl, naphthyl, mono- or di- which may be substituted with 1 to 4 substituents selected from the group consisting of alkyl-carbonyl and benzoyl Alkyl, phenoxy, benzoyl, phenoxycarbonyl, benzylcarbonyl, fennel- Alkyl-carbamoyl, phenylcarbamoyl, phenyl- Alkylcarbonylamino, benzoylamino, phenyl- Alkylsulfonyl, phenylsulfonyl, phenyl- Alkylsulfinyl, panel- May be substituted with 1 to 5 substituents selected from the group consisting of alkylsulfinylamino or phenylsulfonylamino groups Aralkyl, Aryl Alkenyl, Aryl Alkylyl or Cycloalkyl- Alkyl groups, (7) halogen, amino, mono- or di- Alkyl-substituted amino and In the group consisting of alkoxy or Aryl-carbonyl group, (8) halogen, amino, mono- or di- Alkyl-substituted amino and May be substituted with 1 to 3 substituents selected from the group consisting of alkoxy Alkylphosphonyl or May be substituted with one to three substituents selected from the group consisting of an allylsulfonyl group, (9)-or C6-14 alkyl substituted amino and C1-14 alkoxy Alkoxy-carbonyl or Aralkyloxy-carbonyl groups, (1) halogen, amino, mono- or di- Alkyl-substituted amino and Heterocyclic-carbonyl groups which may be substituted with one to three substituents selected from the group consisting of alkoxy, (12) halogen, amino, mono- or di- Alkyl substituted amino and Carbamoyl groups which may be substituted with one to three substituents selected from the group consisting of alkoxy, (13) halogen, amino, mono- or di- Alkyl-substituted amino and Mono- or di- which may be substituted with 1 to 3 substituents selected from the group consisting of alkoxy Alkyl-carbamoyl group or (14) formyl; Independently represents (1 ') hydrogen atom, (2') halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Alkyl-carbonylamino, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carboxyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, Straight or branched chain which may be substituted with 1 to 5 substituents selected from the group consisting of alkylenedioxy and heterocyclic groups Alkyl, Alkynyl, (3 ') halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Alkyl-carbonylamino, Akylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted-carbamoyl, Alkylsulfonyl, May be substituted with 1 to 5 substituents selected from the group consisting of alkylin dioxy and heterocyclic groups Monocyclic cycloalkyl groups, (4 ') halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Alkyl-carbonylamino, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, May be substituted with 1 to 5 substituents selected from the group consisting of alkylenedioxy and heterocyclic groups Bridged saturated hydrocarbon groups, (5 ') Alkyl, halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Alkyl-carbonylamino, Aralkyloxy, aminocarbonyloxy, mono- or di- Alkyl-substituted amino carbamoyl, Alkylsulfonyl, Cycloalkylsulfonyl, and Alkyl, Alkoxy, halogen, hydroxy, benzyloxy, amino, mono- or di- Alkyl-substituted amino, nitro, Phenyl, naphthyl, mono- or di-phenyl- which may be substituted with 1 to 4 substituents selected from the group consisting of alkyl-carbonyl and benzoyl Alkyl, phenoxy, benzoyl, phenoxycarbonyl, benzylcarbonyl, phenyl- Alkyl-carbamoyl, phenylcarbamoyl, phenyl- Alkylcarbonylamino, benzoylamino, phenyl- Alkylsulfonyl, phenylsulfonyl, phenylsulfonyl, phenyl- Alkylsulfinyl, phenyl- Phenyl or naphthyl group (6 ') which may be substituted by 1 to 5 substituents selected from the group consisting of alkylsulfonyl amino or phenylsulfonylamino groups Alkyl, halogen, nitro, cyano, hydroxy, Coxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Alkylcarbonylamino, Aralkyloxy, aminocarbonyloxy, mono- or di- Alkyl-substituted aminocarboxyoxy, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, Cycloalkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, Cycloalkylsulfonyl, and Alkyl, Alkoxy, halogen, hydroxy, benzyloxy, amino mono- or di- Alkyl-substituted amino, nitro, Phenyl, naphthyl, mono- or di- which may be substituted with 1 to 4 substituents selected from the group consisting of alkyl-carbonyl and benzoyl Alkyl, phenoxy, benzoyl, phenoxycarbonyl, benzylcarbonyl, phenyl- Alkyl, phenoxy, benzoyl, phenoxycarbonyl, benzylcarbonyl, phenyl- Alkyl-carbamoyl, phenylcarbamoyl, phenyl- Alkyl-carbonylamino, benzoylamino, moyl, phenylcarbamoyl, phenyl- -Alkylcarbonylamino, benzoylamino, phenyl- Alkylsulfonyl, phenylsulfonyl, phenyl- -Alkylsulfinyl, phenyl- May be substituted with 1 to 5 substituents selected from the group consisting of alkylsulfonylamino or phenylsulfonyl amino groups Cycloalkyl- An alkyl group; May be combined with adjacent nitrogen atoms to form 3- to 13-membered heterocyclic groups having from 1 to 3 nitrogen, oxygen and / or sulfur atoms as hetero atoms in addition to carbon and 2 nitrogen atoms; ) Halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5- to 7-membered cyclic amino, Alkyl-carbonylamino, Alkylsulfonyl amino, Alkoxy-carboxyl, Alkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, Straight or branched chain which may be substituted with 1 to 4 substituents selected from the group consisting of alkylenedioxy and heterocyclic groups Alkyl, Alkenyl or Alkynyl (halogen), nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Alkyl-carbonylamino, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, May be substituted with 1 to 5 substituents selected from the group consisting of alkylenedioxy and heterocyclyl groups Monocyclic cycloalkyl groups (3) halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Alkyl-carbonylamino, Alkylsulfonyl amino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, May be substituted with 1 to 5 substituents selected from the group consisting of alkylenedioxy and heterocyclic groups Bridged saturated hydrocarbons (4) Alkyl, halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino C1-4 alkylcarbonylamino, C7-16 aralkyloxy, aminocarbonyloxy, mono or di-C1-4 alkyl substituted aminone carboxyoxy, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkylsulfonyl, Cycloalkylsulfonyl, Alkylenedioxy, and Alkyl, Alkoxy, halogen, hydroxy, benzyloxy, amino, mono- or di- Alkyl-substituted amino, nitro, Phenyl, naphthyl, mono- or di-phenyl- which may be substituted with 1 to 4 substituents selected from the group consisting of alkyl-carbonyl and benzoyl Alkyl, phenoxy, benzoyl, phenoxycarbonyl, benzylcarbonyl, phenyl- Alkyl-carbamoyl, phenylcarbamoyl, phenyl- Alkyl-carbonylamino, benzoylamino, phenyl- Phenyl or naphthyl groups which may be substituted with 1 to 5 substituents selected from the group consisting of alkylsulfonylamino or phenylsulfonylamino groups (2006.01) Alkyl, halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Alkylcarbonylamino, Aralkyloxy, aminocarbonyloxy, mono- or di- Alkyl-substituted aminocarboxyoxy, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, Cycloalkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, Cycloalkylsulfonyl, Alkylenedioxy, and Alkyl, Alkoxy, halogen, hydroxy, benzyloxy, amino, mono- or di- Alkyl-substituted amino, nitro, Phenyl, naphthyl, mono- or di- which may be substituted with 1 to 4 substituents selected from the group consisting of alkyl-carbonyl and benzoyl Alkyl-carbamoyl, phenylcarbamoyl, pe Alkyl-carbonylamino, benzoylamino, phenyl- Alkylsulfonyl, phenylsulfonyl, phenyl- Alkylsulfinyl, phenyl- May be substituted with 1 to 5 substituents selected from the group consisting of alkylsulfonyl amino or phenylsulfonylamino groups Aralkyl, Aryl Alkenyl, Aryl Alkynyl or Cycloalkyl- Alkyl group, (6) halogen atom, (7) nitro group, (8) cyano group, (9) hydroxyl group, (10) Alkoxy Groups (11) Alkylthio group, (12) amino group, (13) mono or di- Alkylamino Groups (14) Alkyl-carbonylamino groups, (15) Alkyl-sulfonylamino groups, (16) Alkoxy-carbonyl group, (17) Carboxyl group, (18) Formyl group, (19) Alkyl-carbonyl groups, (20) Alkyl-carbonyloxy group, (21) ω-oxo-ω- (tetrahydratebenzoazinyl) Alkyl groups, (22) Alkyl, halogen, Alkoxy, mono- or di- A benzoyl group, (23) carbamoyl group, (24) mono-or di Alkylcarbamoyl groups, (25) Alkylsulfonyl groups, (26) oxo groups and (27) pyridinyl, pyrazinyl, pyrimidinyl, quinolinyl, isoquinolinyl, naphthyridinyl, benzothiazolyl, benzo oxazolyl, furanyl and thiophenyl It may be substituted with 1 to 5 substituents selected from the group consisting of heterocyclic group selected from; Ring A is Alkyl, halogen, nitro, cyano, hydroxy, Alkoxy, Alkylthio, amino, mono- or di- Alkyl-substituted amino, 5 to 7-membered cyclic amino, Carbonylamino, Aralkyloxy, aminocarbonyloxy, mono- or di-alkyl-substituted aminocarboxyoxy, Alkylsulfonylamino, Alkoxy-carbonyl, carboxyl, Alkyl-carbonyl, Cycloalkyl-carbonyl, carbamoyl, mono- or di- Alkyl-substituted carbamoyl, Alkylsulfonyl, Cycloalkylsulfonyl, and Alkyl, Alkoxy, halogen, hydroxy, benzyloxy, amino, mono- or di- Alkyl-substituted amino, nitro, Phenyl, naphthyl, mono- or di- which may be substituted with 1 to 4 substituents selected from the group consisting of alkyl-carbonyl and benzoyl Alkyl, phenoxy, benzoyl, phenoxycarbonyl, benzylcarbonyl, phenyl- Alkyl-carbamoyl, phenylcarbamoyl, phenyl- Alkyl-carbonylamino, benzoylamino, phenyl- Alkylsulfonyl, phenylsulfonyl, phenyl- Alkylsulfonyl, phenyl- A compound which is a benzene ring which may be further substituted by 1-3 substituents selected from the group consisting of alkylsulfonylamino or phenylsulfonylamino. The method of claim 1, (I) a hydrogen atom, or (ii) a hydroxy group Alkyl groups, (iii) Alkynyl, (hal) halogen, nitro, cyano, C1-9, Phenyl which may be substituted with 1 to 3 substituents selected from the group consisting of alkoxy, hydroxy and phenylmethoxy groups Alkyl group, (iii) formyl group, (iii) Alkyl-carbonyl groups, (iii) An alkoxy-carbonyl group, (iii) pyridylcarbonyl group, or (iii) mono- or di- A compound which is an alkyl carbamoyl group. The method of claim 1, (I) H, (ii) straight or branched chain Alkalescence, (ⅲ) Alkyl, halogen, nitro, cyano, hydroxy, Alkoxy and Phenyl which may be substituted with 1 to 3 substituents selected from the group consisting of aralkyloxy Alkyl group, (iii) naphthyl- Alkyl-carbonyl, (iii) Alkyl-carbonyl, (iii) phenyloxycarbonyl or (iii) Alkoxycarbonyl. The method of claim 1, (I) H, (ii) straight or branched chain Alkyl groups, (iii) Alkyl-carbonyl groups, or (iii) Phenyl, which may be substituted by alkoxy Compound which is an alkyl group. The compound of claim 1, wherein k + m is an integer from 2 to 6. 6. The compound of claim 1, wherein k is an integer of 0 to 2 and m is an integer of 2 to 5. The following formula of Claim 1 in Formula [I]. Part of And according to claim 1, (I) H, (ii) straight or branched chain Alkyl groups, (iii) Alkyl-carbonyl groups, or (iii) Phenyl, which may be substituted by alkoxy Compound which is an alkyl group. The compound of claim 1, wherein ring A is a benzene ring. 2. Compounds according to claim 1, wherein n is an integer from 1 to 6. The method of claim 1, Is a hydrogen atom or a phenyl group. The method of claim 1, Is H. The method of claim 1, May independently be substituted with (i) a hydroxy group Phenyl which may be substituted by alkyl group, (ii) phenyl group or (iii) halogen atom An alkyl group, Is bonded together with an adjacent nitrogen atom to form (i ') phenyl- A piperidinyl group which may be substituted with an alkyl group, a hydroxy group or oxo, (ii ') 4-oxo-1-phenyl-1,3,8-triazaspiro [4,5] decan-8-yl, (iii') 1,2,3,4-tetrahydroisoquinolin-2-yl, (iv ') pyrrolidinyl, (v') morpholinyl, (vi ') phenyl- Homopepyrazinyl groups which may be substituted by alkyl groups, or (vii ') (1) halogen atoms, Alkoxy group or Phenyl which may be substituted by alkyldioxy group Alkyl group, (2) pyridyl group, (3) benzoyl group which may be substituted by halogen atom, (4) hydroxy group, 3-oxo-3 [3- (phenylmethyl) -2,3,4,5-tetrahydro-1H May be substituted with a 3-benzazin-7-yl] propyl, pyridyl, furyl or 2-methyl-thiazol-4-yl group Alkyl groups, (5) promil groups, (6) An alkyl-carbonyl group, (7) a phenyl group which may be substituted with a halogen atom, (8) a hydroxyl group, or (9) diphenyl A compound which forms a piperazinyl group which may be substituted with an alkyl group. The method of claim 1, Are bonded together with adjacent nitrogen atoms, (1) formyl, (2) Alkyl-carbonyl, (3) hydroxy, (4) oxo, (5) pyridyl, (6) benzoyl, which may be substituted with 1 to 3 halogen atoms, (7) hydroxy, pyridyl, furyl, thiazole Straight or branched chain which may be substituted with 1 to 3 substituents selected from the group consisting of -4-yl and 2-methyl-thiazol-4-yl Alkyl, (8) halogen, hydroxy and Phenyl which may be substituted with one to three substituents selected from the group consisting of alkylenedioxy, (9) halogen, hydroxy and May be substituted with 1 to 3 substituents selected from the group consisting of alkylenedioxy Aralkyl and (10) Oxo (Tetrahydrobenzazinyl) Pyrrolidinyl, piperidinyl, piperidinyl, piperazinyl, morpholinyl or 1,2,3,4-tetrahydroquinolinyl, which may be substituted with one or two substituents selected from the group consisting of alkyl Compounds that form groups. 2. The compound of claim 1, bonded together with adjacent nitrogen atoms in R ³ and R ⁴ to form (1) formyl, (2) C _1-4 alkyl-carbonyl, (3) hydroxy, (4) oxo, ( 5) pyridyl, (6) benzoyl, which may be substituted with 1 to 3 halogen atoms, (7) hydroxy, pyridyl, furyl, thiazol-4-yl and 2-methyl-thiazol-4-yl 1 to 3 substituents selected from the group consisting of straight or branched C _1-4 alkyl, (8) halogen, hydroxy and C _1-4 alkylenedioxy which may be substituted with ₁ to 3 substituents selected from C _7-18 aralkyl which may be substituted with 1 to 3 substituents selected from the group consisting of phenyl which may be substituted, (9) halogen, hydroxy and C _1-4 alkylenedioxy and (10) ω-oxo -ω- (tetrahydro-benzamide oh Jaffe carbonyl) C _1~6 il kilo blood group which may be substituted one or two zero substitution is selected from the consisting of pyrrolidinyl, piperidinyl, piperazinyl, morpholinyl, Paul Needle or 1,2,3,4-tetrahydro-quinolinyl compound to form a carbonyl. The method of claim 1, Is combined with an adjacent nitrogen atom to form 4- (phenylmethyl) -pyrerazin-1-yl or 4-[(2-methylthiazol-4) methyl] piperazin-1-yl. A compound according to claim 1 wherein N is an integer of 3-8 when the group of does not form a heterocyclic group, and n is an integer of 2-5 when the group forms a heterocyclic group. A compound according to claim 1 which is a compound of the formula or a pharmaceutically acceptable salt thereof: [Wherein, Is (i) Alkyl groups or (ii) Phenyl which may be substituted with an alkoxy group Alkyl group] The compound of claim 1, wherein 1- [3- [4- (methoxyphenyl) methyl] -2,3,4,5-tetrahydro-1H-3-benzazin-7-yl] -3- [4 -(Phenylmethyl) piperazin-1-yl] -1-propanone or a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein 1- [3- [4- (phenylethyl)]-2,3,4,5-tetrahydro-1H-3-benzazin-7-yl] -3- [4- ( Phenylmethyl) piperazin-1-yl] -1-propanone or a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein 1- [3- [4- (methylpropyl)]-2,3,4,5-tetrahydro-1H-3-benzazin-7-yl] -3- [4- ( Phenylmethyl) piperazin-1-yl] -1-propanone or a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein 1- [3- [4- (phenylmethyl)]-2,3,4,5-tetrahydro-1H-3-benzazin-7-yl] -3- [4- ( Phenylmethyl) piperazin-1-yl] -1-propanone or a pharmaceutically acceptable salt thereof. The compound according to claim 1, wherein 1- [1- [4- (phenylmethyl)]-2,3-dihydro-1H-indol-5-yl] -3- [4- (phenylmethyl) piperazin-1- Il] -1-propanone or a pharmaceutically acceptable salt thereof. The compound according to claim 1, wherein 1- [2- (phenylmethyl) -2,3,4,5-dihydro-1H-indol-2-5-yl] -3- [4- (phenylmethyl) piperazine- 1-yl] -1-propanone or a pharmaceutically acceptable salt thereof. The compound of claim 1, wherein 3- [4-[(2-methylthiazol-4-yl) methyl] piperazin-1-yl] -1- [3- (phenylmethyl) -2,3,4,5 -Tetrahydro-1H-3-benzazin-7-yl] -1-propanone or a pharmaceutically acceptable salt thereof. A compound of formula (II) or a salt thereof: [Wherein, Y is a leaving group; , Ring A, , n, k and m have the same meanings as defined in claim 1. A process for preparing a compound of formula [I] or a pharmaceutically acceptable salt thereof, wherein the compound of formula (II) or a salt thereof is reacted with a compound of formula [III] or a salt thereof: [In the above formula, Is H, an optionally substituted hydrocarbon group or an optionally substituted acyl group; Ring A is a more substituted benzene ring; n is an integer of 1 to 10; Are independently H is an optionally substituted hydrocarbon group; May combine with an adjacent nitrogen atom to form an optionally substituted heterocyclic group; In the repetition of n, They may be different from each other; k is an integer of 0 to 3; m is an integer of 1-8; When k = 0 and m = 2, n is an integer greater than or equal to 2 and Y is a leaving group.] A compound of formula [IV] or a pharmaceutically acceptable compound thereof, characterized by reacting a compound of formula [IV] or a salt thereof and a compound of formula [V] with a compound of formula [III] Preparation of salts: [Wherein, Is H, an optionally substituted hydrocarbon group or an optionally substituted acyl group; Ring A is a more substituted benzene ring; Are independently H is an optionally substituted hydrocarbon group; May combine with adjacent nitrogen atoms to form an optionally substituted heterocyclic group; k is an integer of 0 to 3; m is an integer of 1-8; Provided that when k = 0 and m = 2, n is an integer of 2 or more, Is H or an optionally substituted hydrocarbon group; Is H or an optionally substituted hydrocarbon group] Cholinesterase inhibitors containing a compound of formula [VII] or a pharmaceutically acceptable salt thereof: [Wherein, silver -N ( Is H, an optionally substituted hydrocarbon group or an optionally substituted acyl group, O or S; Ring A is a more substituted benzene ring; n is an integer from 1 to 10; Are independently H is an optionally substituted hydrocarbon group; May combine with adjacent nitrogen atoms to form an optionally substituted heterocyclic group; in the repetition of n They may be different from each other; k is an integer of 1 to 3; m is an integer of 1 to 8] Induced by acetylcholinesterase activity characterized by containing an effective amount of cholinesterase inhibitory and a pharmacologically acceptable carrier of a compound of formula [I] or a pharmaceutically acceptable salt thereof according to claim 1 Pharmaceutical composition against the disease. A disease caused by acetyllin esterase activity characterized by containing an effective amount of cholinesterase inhibitory and a pharmacologically acceptable carrier of a compound of formula [VII] or a pharmaceutically acceptable salt thereof Pharmaceutical composition for. The pharmaceutical composition of claim 30, wherein the disease is senile dementia and / or Alzheimer's disease. The pharmaceutical composition of claim 31, wherein the disease is senile dementia and / or Alzheimer's disease. To a mammal suffering from a disease caused by therapase activity in acetylcholine with a therapeutically effective amount of a cholinesterase inhibitory effective amount of a compound of the formula or a pharmaceutically acceptable salt thereof and a pharmacologically acceptable carrier: Method of treatment for diseases caused by acetylcholinesterase activity, characterized by administering: [Wherein, silver -N ( Is H, an optionally substituted hydrocarbon group or an optionally substituted acyl group, O or S; Ring A is a more substituted benzene ring; n is an integer from 1 to 10; Are independently H is an optionally substituted hydrocarbon group; May combine with adjacent nitrogen atoms to form an optionally substituted heterocyclic group; in repetition of n They may be different from each other; k is an integer of 1-3; m is an integer of 1 to 8] The method of claim 34, wherein the disease is senile dementia and / or Alzheimer's disease. Use of a compound of the formula [VII] or a pharmaceutically acceptable salt thereof as a preparation component of a cholinesterase inhibitor: [Wherein, silver -N ( Is H, an optionally substituted hydrocarbon group or an optionally substituted acyl group, O or S; Ring A is a more substituted benzene ring; n is an integer from 1 to 10; Are independently H is an optionally substituted hydrocarbon group; May combine with adjacent nitrogen atoms to form an optionally substituted heterocyclic group; in the repetition of n They may be different from each other; k is an integer of 1-3; m is an integer of 1 to 8] ※ Note: The disclosure is based on the initial application.