KR900018036A

KR900018036A - 4 (1H) -quinolone derivative

Info

Publication number: KR900018036A
Application number: KR1019890006934A
Authority: KR
Inventors: 다츠시 오사와; 히데오 오타; 코지 아키모토; 가츠히코 하라다; 히로시 소가; 야스히로 진노
Original assignee: 모토야마 히데요; 기린비루 가부시키가이샤
Priority date: 1988-05-24
Filing date: 1989-05-24
Publication date: 1990-12-20

Abstract

내용 없음No content

Description

4(1H)-퀴놀론 유도체4 (1H) -quinolone derivative

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음Since this is an open matter, no full text was included.

Claims

다음 일반식(I)로 표시되는 퀴놀론 유도체와 약제학적으로 허용가능한 그의 염.Quinolone derivatives represented by the following general formula (I) and pharmaceutically acceptable salts thereof.

상기식에서, A는 수소원자이고, Y는 산소원자 또는 황원자이고, R은 탄소원자수 1내지 4의 직쇄 또는 분쇄형 알콕시기 또는 알케닐옥시기, 벤질옥시기, 탄소원자수 1내지 4의 직쇄 또는 분쇄형 알킬기 또는 알케닐기, 탄소원자수 1내지 4의 디알킬아미노기 페닐기, 염소원자, 벤조일기, 탄소원자수 1내지4의 알킬슬페닐기, 알킬술피닐기 또는 알킬술포닐기, 또는 메틸렌디옥시기이고, n은 2이며, 두개의 R은 서로 같거나 다를 수도 있는 것으로 이들은 각각 퀴놀론모핵의 6-위치와 7-위치, 또는 6-위치와 8-위치에 치환되고, R¹은 수소원자, 탄소원자수 1내지 6의 직쇄 또는 분쇄형 알킬기 또는 알케닐기, 벤질기, 또는 탄소원자수 1내지 4의 저급알콕시기 및/또는 할로겐원자로 치환된 벤질기이며, Z는 수소원자, 사이클로프로필기, 2-또는 3-티에닐기, 2-또는 3-퓨릴기, 2-또는 3-피롤릴기, 또는 2-, 3- 또는 4-피리딜기이다.Wherein A is a hydrogen atom, Y is an oxygen atom or a sulfur atom, and R is a straight or pulverized alkoxy group or alkenyloxy group, benzyloxy group, or carbon atom of 1 to 4 carbon atoms of 1 to 4 carbon atoms An alkyl group or an alkenyl group, a dialkylamino group having 1 to 4 carbon atoms, a phenyl group, a chlorine atom, a benzoyl group, an alkylsulphenyl group having 1 to 4 carbon atoms, an alkylsulfinyl group or an alkylsulfonyl group, or a methylenedioxy group, n is 2 The two R's may be the same as or different from each other, and are substituted at the 6- and 7-positions, or the 6- and 8-positions of the quinolone nucleus, respectively, and R ¹ is a hydrogen atom and a straight chain having 1 to 6 carbon atoms. Or a branched alkyl group or alkenyl group, benzyl group, or a lower alkoxy group having 1 to 4 carbon atoms and / or a benzyl group substituted with a halogen atom, Z is a hydrogen atom, a cyclopropyl group, 2- or 3-thienyl group, 2 Or 3-furyl , 2-or 3-pyrrolyl group, or a 2-, 3- or 4-pyridyl group-.

다음 일반식(I')로 표시되는 다음의 화합물들 중에서 선택되는 퀴놀론 유도체와 약제학적으로 허용가능한 그의 염.Quinolone derivatives selected from the following compounds represented by the following general formula (I ') and pharmaceutically acceptable salts thereof.

상기식에서, 각 치환기들은 다음에서 선택되는 화합물에 상응하는 각 치환기를 나타낸다: 5-히드록시-6-메톡시-4(1H)-퀴놀론;6-히드록시-5-메톡시-4(1H)-퀴놀론;8-히드록시-7-메톡시-4(1H)-퀴놀론;5-벤질옥시-6-메톡시-4(1H)-퀴놀론;3-에톡시카르보닐-5-메톡시-8-메톡시메톡기-4(1H)-퀴놀론;8-시아노-4(1H)-퀴놀론;5-시아노-4(1H)-퀴놀론;6-아세톡시-4(1H)-퀴놀론;6-아세톡시-1-아세틸-4(1H)-퀴놀론;8-메톡시-1-메틸-4(1H)-퀴놀론;5.8-디에톡시-4(1H)-퀴놀론;8-i-프로필-4(1H)-퀴놀론;8-메톡시-5-메틸-4(1H)-퀴놀론;5-메톡시-8-페닐-4(1H)-퀴놀론;7,8-디멕톡시-4(1H)-퀴놀론;5-메톡시-8-메틸슬페닐-4(1H)-퀴놀론;6,7,8-트리메톡시-4(1H)-퀴놀론;5-히드록시-7-메톡시-4(1H)-퀴놀론;8-시아노-3-에톡시카르보닐-4(1H)-퀴놀론;6,7-디메톡시-3-메톡시카르보닐-1-메틸-4(1H)-퀴놀론;3-에톡시카르보닐-1-에틸-6-메틸-(1H)-퀴놀론;7-에톡시-3-에톡시카르보닐-1-에틸-6-메톡시-4(1H)-퀴놀론;3-에톡시카르보닐-8-메톡시-4(1H)-퀴놀론;3-에톡시카르보닐-8-메톡시-5-페닐-(1H)-퀴놀론; 3-에톡시카르보닐-8-메톡시-5-페닐-(1H)퀴놀린;7,8-디메톡시-3-에톡시카르보닐-1-에틸-4(1H)-퀴놀론;3-에톡시카르보닐-1-에틸-8-메톡시-6-메틸술피닐-4(1H)-퀴놀론;3-에톡시카르보닐-1-에틸-8-메톡시-6-케닐술피닐-4(1H)-퀴놀론;6,7-디메톡시-3-히드록시메틸-4(1H)-퀴놀론;6,7-디메톡시-3-히드록시메틸-1-메틸-4(1H)-퀴놀론;3-카르복실-1-메틸-5,6,7-트리메톡시-4(1H)-퀴놀론;8-아세틸-4(1H)-퀴놀론;6-시아노메틸-4(1H)-퀴놀론;6-[2-트란스(2,5--디메톡시페닐)비닐]-4(1H)-퀴놀론;7,8-디메틸-1-에틸-4(1H)-퀴놀론;7-[(1,3-디옥솔란-2-일)메톡시]-6-메톡시-4(1H)-퀴놀론;6-메톡시-7-메톡시-메톡시-4(1H)-퀴놀론;6-메톡시-7-메틸-4(1H)-퀴놀론;1-에틸-7-메틸-4(1H)-퀴놀론;1-에틸-6-메틸-4(1H)-퀴놀론;1-에틸-5-히드록시-8-메틸-4(1H)-퀴놀론;6-(2-히드록시)에틸-4(1H)-퀴놀론;6-에톡시카르보닐-4(1H)-퀴놀론;1-에틸-8-메톡시-5-페닐-4(1H)-퀴놀론;7-피페리지닐-4(1H)-퀴놀론;8-(2-프로페닐)-4(1H)-퀴놀론;8-(2-트란스-부테닐)-7-히드록시-6-메톡시-4(1H)-퀴놀론;1-에틸-6-메톡시-4(1H)-퀴놀론;6-에톡시-1-에틸-4(1H)-퀴놀론;, 1,6-디에틸-4(1H)-퀴놀론;6-에톡시-3-에톡시카르보닐-8-메톡시-4(1H)-퀴놀론;6-에톡시-3-에톡시카르보닐-1-에틸-8-메톡시-4(1H)-퀴놀론;8-에톡시-3-에톡시카르보닐-1-에틸-6-메톡시-4(1H)-퀴놀론;5-에톡시-3-[(2-에톡시)에톡시카르보닐-8-메톡시-4(1H)-퀴놀론;3-에톡시카르보닐-8-메록시-4(1H)-티오퀴놀론;7,8-디메틸-3-에톡시카르보닐-1-에틸-4(1H)-퀴놀론;5-아세톡시-3-에톡시카르보닐-1-에틸-8-메틸-4(1H)-퀴놀론;3-에톡시카르보닐-8-페닐술포닐-4(1H)-퀴놀론;6-디에틸아미노-3-에톡시카르보닐-8-메틸-4(1H)-퀴놀론;1,6-디메틸-3-에톡시카르보닐-4(1H)-퀴놀론;3-카르복실-6-에톡시-1-에틸-7-메톡시-4(1H)-퀴놀론;3-카르복실-1-에틸-5-메틸-4(1H)-퀴놀론;3-카르복실-7,8-디메틸-6-에톡시-1-에틸-4(1H)-퀴놀론;3-카르복실-6-에톡시-1,7,8-트리메틸-4(1H)-퀴놀론;3-카르복실-1-에틸-6-메틸-4(1H)-퀴놀론:3-카르복실-8-메톡시5-페닐-4(1H)-퀴놀론:3-카르복실-7-에톡시-6-메톡시-1-메틸-4(1H)-퀴놀론:3-카르복실-7에톡시-6-메톡시-1-n-프로필-4(1H)-퀴놀론;2-사이클로프로필-4(1H)-퀴놀론;1-에틸-2-(2-티에닐)-4(1H)-퀴놀론;5-벤질옥시-6-메톡시-2-(3-피리딜)-4(1H)-퀴놀론;2-(2-티에닐)-4(1H)-퀴놀론;6,7-디메톡시-3-(4-페닐피페리디닐)카르보닐-4(1H)-퀴놀론;8-메톡시-5-메틸-3-(4-페닐리페리디닐)카르보닐-4(1H)-퀴놀론;8-메톡시-1-메틸-3-{1-[4-(3,4-메틸렌디옥시벤질)-피페라지닐]카르보닐-4(1H)-퀴놀론;1-에틸-3-{1-[4-(2-메톡시페닐)피페라지닐]카르보닐}-6-메틸-4(1H)-퀴놀론;3-{1-[4-(2-메톡시페닐)피페라지닐]카르보닐}-6-메틸-4(1H)-퀴놀론;6,7-디메톡시-1-에틸-3-{1-[4-(4-니트로페닐)피페라지닐]카르보닐}-4(1H)-퀴놀론;6-[2-트란스-(2,5-디메톡시페닐)비닐]-1-에틸-4(1H)-퀴놀론; 및 2-사이클로프로필-1-에틸-4(1H)-퀴놀론;Wherein each substituent represents each substituent corresponding to the compound selected from: 5-hydroxy-6-methoxy-4 (1H) -quinolone; 6-hydroxy-5-methoxy-4 (1H) -Quinolone; 8-hydroxy-7-methoxy-4 (1H) -quinolone; 5-benzyloxy-6-methoxy-4 (1H) -quinolone; 3-ethoxycarbonyl-5-methoxy-8 -Methoxymethoxy-4 (1H) -quinolone; 8-cyano-4 (1H) -quinolone; 5-cyano-4 (1H) -quinolone; 6-acetoxy-4 (1H) -quinolone; 6 -Acetoxy-1-acetyl-4 (1H) -quinolone; 8-methoxy-1-methyl-4 (1H) -quinolone; 5.8-diethoxy-4 (1H) -quinolone; 8-i-propyl-4 (1H) -quinolone; 8-methoxy-5-methyl-4 (1H) -quinolone; 5-methoxy-8-phenyl-4 (1H) -quinolone; 7,8-dimethoxy-4 (1H)- Quinolone; 5-methoxy-8-methylsulfen-4 (1H) -quinolone; 6,7,8-trimethoxy-4 (1H) -quinolone; 5-hydroxy-7-methoxy-4 (1H ) -Quinolone; 8-cyano-3-ethoxycarbonyl-4 (1H) -quinolone; 6,7-dimethoxy-3-methoxycarbonyl-1-methyl-4 (1H) -quinolone; 3- Ethoxycarbonyl-1-ethyl-6-methyl- (1H) -quinol Ron; 7-ethoxy-3-ethoxycarbonyl-1-ethyl-6-methoxy-4 (1H) -quinolone; 3-ethoxycarbonyl-8-methoxy-4 (1H) -quinolone; 3 Ethoxycarbonyl-8-methoxy-5-phenyl- (1H) -quinolone; 3-ethoxycarbonyl-8-methoxy-5-phenyl- (1H) quinoline; 7,8-dimethoxy-3-ethoxycarbonyl-1-ethyl-4 (1H) -quinolone; 3-ethoxy Carbonyl-1-ethyl-8-methoxy-6-methylsulfinyl-4 (1H) -quinolone; 3-ethoxycarbonyl-1-ethyl-8-methoxy-6-kenylsulfinyl-4 (1H ) -Quinolone; 6,7-dimethoxy-3-hydroxymethyl-4 (1H) -quinolone; 6,7-dimethoxy-3-hydroxymethyl-1-methyl-4 (1H) -quinolone; 3- Carboxyl-1-methyl-5,6,7-trimethoxy-4 (1H) -quinolone; 8-acetyl-4 (1H) -quinolone; 6-cyanomethyl-4 (1H) -quinolone; 6- [2-trans (2,5--dimethoxyphenyl) vinyl] -4 (1H) -quinolone; 7,8-dimethyl-1-ethyl-4 (1H) -quinolone; 7-[(1,3-diox Solan-2-yl) methoxy] -6-methoxy-4 (1H) -quinolone; 6-methoxy-7-methoxy-methoxy-4 (1H) -quinolone; 6-methoxy-7-methyl -4 (1H) -quinolone; 1-ethyl-7-methyl-4 (1H) -quinolone; 1-ethyl-6-methyl-4 (1H) -quinolone; 1-ethyl-5-hydroxy-8-methyl -4 (1H) -quinolone; 6- (2-hydroxy) ethyl-4 (1H) -quinolone; 6-ethoxycarbonyl-4 (1H) -quinolone; 1-ethyl-8-methoxy-5- Phenyl-4 (1H) -quinolone; 7-piperidinyl-4 (1H) -quinolone; 8- (2-propenyl) -4 (1H) -quinolone; 8- (2-trans-butenyl) -7 -Hydroxy-6-methoxy-4 (1H) -quinolone; 1-ethyl-6-methoxy-4 (1H) -quinolone; 6-ethoxy-1-ethyl-4 (1H) -quinolone ;, 1 , 6-diethyl-4 (1H) -quinolone; 6-ethoxy-3-ethoxycarbonyl-8-methoxy-4 (1H) -quinolone; 6-ethoxy-3-ethoxycarbonyl-1 -Ethyl-8-methoxy-4 (1H) -quinolone; 8-ethoxy-3-ethoxycarbonyl-1-ethyl-6-methoxy-4 (1H) -quinolone; 5-ethoxy-3- [(2-Ethoxy) ethoxycarbonyl-8-methoxy-4 (1H) -quinolone; 3-ethoxycarbonyl-8-methoxy-4 (1H) -thioquinolone; 7,8-dimethyl- 3-ethoxycarbonyl-1-ethyl-4 (1H) -quinolone; 5-acetoxy-3-ethoxycarbonyl-1-ethyl-8-methyl-4 (1H) -quinolone; 3-ethoxycar Bonyl-8-phenylsulfonyl-4 (1H) -quinolone; 6-diethylamino-3-ethoxycarbonyl-8-methyl-4 (1H) -quinolone; 1,6-dimethyl-3-ethoxycar Bonyl-4 (1H) -quinolone; 3-carboxy-6-ethoxy-1-ethyl-7-methoxy-4 (1H) -quinolone; 3-car Reboxyl-1-ethyl-5-methyl-4 (1H) -quinolone; 3-carboxy-7,8-dimethyl-6-ethoxy-1-ethyl-4 (1H) -quinolone; 3-carboxyl- 6-ethoxy-1,7,8-trimethyl-4 (1H) -quinolone; 3-carboxyl-1-ethyl-6-methyl-4 (1H) -quinolone: 3-carboxy-8-methoxy5 -Phenyl-4 (1H) -quinolone: 3-carboxyl-7-ethoxy-6-methoxy-1-methyl-4 (1H) -quinolone: 3-carboxyl-7ethoxy-6-methoxy- 1-n-propyl-4 (1H) -quinolone; 2-cyclopropyl-4 (1H) -quinolone; 1-ethyl-2- (2-thienyl) -4 (1H) -quinolone; 5-benzyloxy- 6-methoxy-2- (3-pyridyl) -4 (1H) -quinolone; 2- (2-thienyl) -4 (1H) -quinolone; 6,7-dimethoxy-3- (4-phenyl Piperidinyl) carbonyl-4 (1H) -quinolone; 8-methoxy-5-methyl-3- (4-phenyllipridinyl) carbonyl-4 (1H) -quinolone; 8-methoxy-1- Methyl-3- {1- [4- (3,4-methylenedioxybenzyl) -piperazinyl] carbonyl-4 (1H) -quinolone; 1-ethyl-3- {1- [4- (2- Methoxyphenyl) piperazinyl] carbonyl} -6-methyl-4 (1H) -quinolone; 3- {1- [4- (2-methoxyphenyl) piperazinyl] carbonyl} -6-methyl- 4 (1H) -quinol Ron; 6,7-dimethoxy-1-ethyl-3- {1- [4- (4-nitrophenyl) piperazinyl] carbonyl} -4 (1H) -quinolone; 6- [2-trans- ( 2,5-dimethoxyphenyl) vinyl] -1-ethyl-4 (1H) -quinolone; And 2-cyclopropyl-1-ethyl-4 (1H) -quinolone;

제2항에 있어서, 상기 퀴놀린 유도체(I')는 다음 화합물들중에서 선택되는 것임을 특징으로 하는 퀴놀론 유도체와 약제학적으로 허용가능한 그의 염. 3-에톡시카르보닐-8-메톡시-5-페닐-4(1H)-퀴놀론;7-피페라지닐-4(1H)-퀴놀론; 8-(2-트란스-부테닐)-7-히드록시-6-메톡시-4(1H)-퀴놀론; 6-에톡시-3-에톡시카르보닐-8-메톡시-4(1H)-퀴놀론; 6-에톡시-3-에톡시카르보닐-1-에틸-8-메톡시-4(1H)-퀴놀론; 8-에톡시-3-에톡시카르보닐-1-에틸-6-메톡시-4(1H)-퀴놀론; 6-디에틸아미노-3-에톡시카르보닐-8-메틸-4(1H)-퀴놀론; 1,6-디에틸-3-에톡시카르보닐-4(1H)-퀴놀론; 3-카르복실-7-에톡시-6-메톡시-1-메틸-4(1H)-퀴놀론;1-에틸-2-(2-티에닐)-4(1H)-퀴놀린;2-(2-티에닐)-4(1H)-퀴놀론; 및 2-사이클로프로필-1-에틸-4(1H)-퀴놀론.The quinolone derivative and pharmaceutically acceptable salt thereof according to claim 2, wherein the quinoline derivative (I ') is selected from the following compounds. 3-ethoxycarbonyl-8-methoxy-5-phenyl-4 (1H) -quinolone; 7-piperazinyl-4 (1H) -quinolone; 8- (2-trans-butenyl) -7-hydroxy-6-methoxy-4 (1H) -quinolone; 6-ethoxy-3-ethoxycarbonyl-8-methoxy-4 (1H) -quinolone; 6-ethoxy-3-ethoxycarbonyl-1-ethyl-8-methoxy-4 (1H) -quinolone; 8-ethoxy-3-ethoxycarbonyl-1-ethyl-6-methoxy-4 (1H) -quinolone; 6-diethylamino-3-ethoxycarbonyl-8-methyl-4 (1H) -quinolone; 1,6-diethyl-3-ethoxycarbonyl-4 (1H) -quinolone; 3-carboxy-7-ethoxy-6-methoxy-1-methyl-4 (1H) -quinolone; 1-ethyl-2- (2-thienyl) -4 (1H) -quinoline; 2- (2 -Thienyl) -4 (1H) -quinolone; And 2-cyclopropyl-1-ethyl-4 (1H) -quinolone.

다음 일반식(I) 또는 (I')로 표시되는 퀴놀론 유도체 하나이상을 유효성분으로 함유하는 것을 특징으로 하는 강심제.A cardiac agent comprising at least one quinolone derivative represented by the following general formula (I) or (I ') as an active ingredient.

상기식에서, A는 수소원자고, Y는 산소원자 또는 황원자이고, R은 탄소원자수 1내지 4의 직쇄 또는 분쇄형 알콕시기 또는 알케닐옥시기, 벤질옥시기, 탄소원자수 1 내지 4의 직쇄 또는 분쇄형 알킬기 또는 알케닐기, 탄소원자수 1 내지 4의 디알킬아미노기, 페닐기, 염소원자, 벤조일기, 탄소원자수 1 내지 4의 알킬술페닐기, 알킬술피닐기 또는 알킬술포닐기, 또는 메틸렌옥시기이고, n은 2이며, 두개의 R은 서로 같거나 다를 수도 있는 것으로 이들은 각각 퀴놀론모핵의 6-위치와 7-위치, 또는 6-위치와 8-위치에 치환되고, R¹은 수소원자, 탄소원자 수 1 내지 6의 직쇄 또는 분쇄형 알킬기 또는 알케닐기, 벤질기, 또는 탄소원자수 1 내지 4의 저급알콕시기 및/또는 할로겐원자로 치환된 벤질기이며, Z는 수소원자, 사이클로프로필기, 2-또는 3-티에닐기, 2- 또는 3-퓨릴기, 2- 또는 3-피롤릴기, 또는 2-, 3- 또는 4-피리딜기이다.Wherein A is a hydrogen atom, Y is an oxygen atom or a sulfur atom, and R is a straight or pulverized alkoxy group having 1 to 4 carbon atoms or an alkenyloxy group, benzyloxy group, or a straight or pulverized type having 1 to 4 carbon atoms Alkyl group or alkenyl group, dialkylamino group having 1 to 4 carbon atoms, phenyl group, chlorine atom, benzoyl group, alkylsulphenyl group having 1 to 4 carbon atoms, alkylsulfinyl group or alkylsulfonyl group, or methyleneoxy group, n is 2 Two R's may be the same as or different from each other, and are substituted at the 6- and 7-positions, or the 6- and 8-positions of the quinolone nucleus, respectively, and R ¹ is a hydrogen atom or a carbon number of 1 to 6 Is a straight-chain or crushed alkyl group or alkenyl group, benzyl group, or a lower alkoxy group having 1 to 4 carbon atoms and / or a benzyl group substituted with a halogen atom, Z is a hydrogen atom, a cyclopropyl group, 2- or 3-thienyl group , 2- or 3-pew A group, a 2- or 3-pyrrolyl group, or a 2-, 3- or 4-pyridyl group-.

상기식에서, 각 치환기들은 다음에서 선택되는 화합물에 상응하는 각 치환기를 나타낸다; 5-히드록시-6-메톡시-4(1H)-퀴놀론;6-히드록시-5-메톡시-4(1H)-퀴놀론;8-히드록시-7-메톡시-4(1H)-퀴놀론;5-벤질옥시-6-메톡시-4(1H)-퀴놀론;3-에톡시카르보닐-5-메톡시-8-메톡시메톡기-4(1H)-퀴놀론;8-시아노-4(1H)-퀴놀론;5-시아노-4(1H)-퀴놀론;6-아세톡시-4(1H)-퀴놀론;6-아세톡시-1-아세틸-4(1H)-퀴놀론;8-메톡시-1-메틸-4(1H)-퀴놀론;5.8-디에톡시-4(1H)-퀴놀론;8-i-프로필-4(1H)-퀴놀론;8-메톡시-5-메틸-4(1H)-퀴놀론;5-메톡시-8-메틸-4(1H)-퀴놀론;7,8-디멕톡시-4(1H)-퀴놀론;5-메톡시-8-메틸슬페닐-4(1H)-퀴놀론;6,7,8-트리메톡시-4(1H)-퀴놀론;5-히드록시-7-메톡시-4(1H)-퀴놀론;8-시아노-3-에톡시카르보닐-4(1H)-퀴놀론;6,7-디메톡시-3-메톡시카르보닐-1-메틸-4(1H)-퀴놀론;3-에톡시카르보닐-1-에틸-6-메틸-4(1H)-퀴놀론;7-에톡시-3-에톡시카르보닐-1-에틸-6-메톡시-4(1H)-퀴놀론;3-에톡시카르보닐-8-메톡시-4(1H)-퀴놀론;3-에톡시카르보닐-8-메톡시-5-메틸-4(1H)-퀴놀론;3-에톡시카르보닐-8-메톡시-5-페닐-4(1H)-퀴놀론;7,8-디메톡시-3-에톡시카르보닐-1-에틸-4(1H)-퀴놀론;3-에톡시카르보닐-1-에틸-8-메톡시-6-메틸술피닐-4(1H)-퀴놀론;3-에톡시카르보닐-1-에틸-8-메톡시-6-메틸술포닐-4(1H)퀴놀론;6,7-디메톡시-3-히드록시메틸-4(1H)-퀴놀론;6,7-디메톡시-3-히드록시메틸-1-메틸-4(1H)-퀴놀론;3-카르복실-1-메틸-5,6,7-트리메톡시-4(1H)-퀴놀론;8-아세틸-4(1H)-퀴놀론;6-시아노메틸-4(1H)-퀴놀론;6-[2-트란스(2,5--디메톡시페닐)비닐]-4(1H)-퀴놀론;7,8-디메틸-1-에틸-4(1H)-퀴놀론;7-[(1,3-디옥솔란-2-일)메톡시]-6-메톡시-4(1H)-퀴놀론;6-메톡시-7-메톡시메톡시-4(1H)-퀴놀론;6-메톡시-7-메틸-4(1H)-퀴놀론;1-에틸-7-메틸-4(1H)-퀴놀론;1-에틸-6-메틸-4(1H)-퀴놀론;1-에틸-5-히드록시-8-메틸-4(1H)-퀴놀론;6-(2-히드록시)에틸-4(1H)-퀴놀론;6-에톡시카르보닐-4(1H)-퀴놀론;1-에틸-8-메톡시-5-페닐-4(1H)-퀴놀론;7-피페리지닐-4(1H)-퀴놀론;8-(2-프로페닐)-4(1H)-퀴놀론;8-(2-트란스-부테닐)-7-히들옥시-6-메톡시-4(1H)-퀴놀론;1-에틸-6-메톡시-4(1H)-퀴놀론;6-에톡시-1-에틸-4(1H)-퀴놀론;, 1,6-디에틸-4(1H)-퀴놀론;6-에톡시-3-에톡시카르보닐-8-메톡시-4(1H)-퀴놀론;6-에톡시-3-에톡시카르보닐-1-에틸-8-메톡시-4(1H)-퀴놀론;8-에톡시-3-에톡시카르보닐-1-에틸-8-메톡시-4(1H)-퀴놀론;5-에톡시-3-[(2-에톡시)에톡시카르보닐-8-메톡시-4(1H)-퀴놀론;3-에톡시카르보닐-8-메톡시-4(1H)-티오퀴놀론;7,8-디메틸-3-에톡시카르보닐-1-에틸-4(1H)-퀴놀론;5-아세톡시-3-에톡시카르보닐-1-8-메틸-4(1H)-퀴놀론;3-에톡시카르보닐-8-페닐술포닐-4(1H)-퀴놀론;6-디에틸아미노-3-에톡시카르보닐-8-메틸-4(1H)-퀴놀론;1,6-디메틸-3-에톡시카르보닐-4(1H)-퀴놀론;3-카르복실-6-에톡시-1-에틸-7-메톡시-4(1H)-퀴놀론;3-카르복실-1-에틸-5-메틸-4(1H)-퀴놀론;3-카르복실-7,8-디메틸-6-에톡시-1-에틸-4(1H)-퀴놀론;3-카르복실-6-에톡시-1,7,8-트리메틸-4(1H)-퀴놀론;3-카르복실-1-에틸-6-메틸-4(1H)-퀴놀론;3-카르복실-8-메톡시-5-페닐-4(1H)-퀴놀론;3-카르복실-7-에톡시-6-메톡시-1-메틸-4(1H)퀴놀론;3-카르복실-7-에톡시-6-메톡시-1-n-프로필-4(1H)-퀴놀론;2-사이클로프로필-4(1H)-퀴놀론;1-에틸-2-(2-티에닐)-4(1H)-퀴놀론;5-벤질옥시-6-메톡시-2-(3-피리딜)-4(1H)-퀴놀론;2-(2-티에닐)-4(1H)-퀴놀론;6,7-디메톡시-3-(4-페닐피페리디닐)카르보닐-4(1H)-퀴놀론;8-메톡시-5-메틸-3-(4-페닐리페리디닐)카르보닐-4(1H)-퀴놀론;8-메톡시-1-메틸-3-{1-[4-(3,4-메틸렌디옥시벤질)-피페라지닐]카르보닐-4(1H)-퀴놀론;1-에틸-3-{1-[4-(2메톡시페닐)피페라지닐]카르보닐}-6-메틸-4(1H)-퀴놀론;3-{1-[4-(2-메톡시페닐)피페라지닐]카르보닐}-6-메틸-4(1H)-퀴놀론;6,7-디메톡시-1-에틸-3-{1-[4-(4-니트로페닐)피페라지닐]카르보닐}-4(1H)-퀴놀론;6-[2-트란스-(2,5-디메톡시페닐)비닐]-1-에틸-4(1H)-퀴놀론; 및 2-사이클로프로필-1-에틸-4(1H)-퀴놀론;Wherein each substituent represents each substituent corresponding to the compound selected from: 5-hydroxy-6-methoxy-4 (1H) -quinolone; 6-hydroxy-5-methoxy-4 (1H) -quinolone; 8-hydroxy-7-methoxy-4 (1H) -quinolone 5-Benzyloxy-6-methoxy-4 (1H) -quinolone; 3-ethoxycarbonyl-5-methoxy-8-methoxymethoxy group-4 (1H) -quinolone; 8-cyano-4 (1H) -quinolone; 5-cyano-4 (1H) -quinolone; 6-acetoxy-4 (1H) -quinolone; 6-acetoxy-1-acetyl-4 (1H) -quinolone; 8-methoxy -1-Methyl-4 (1H) -quinolone; 5.8-diethoxy-4 (1H) -quinolone; 8-i-propyl-4 (1H) -quinolone; 8-methoxy-5-methyl-4 (1H) -Quinolone; 5-methoxy-8-methyl-4 (1H) -quinolone; 7,8-dimethoxy-4 (1H) -quinolone; 5-methoxy-8-methylsulfen-4 (1H) -quinolone ; 6,7,8-trimethoxy-4 (1H) -quinolone; 5-hydroxy-7-methoxy-4 (1H) -quinolone; 8-cyano-3-ethoxycarbonyl-4 (1H ) -Quinolone; 6,7-dimethoxy-3-methoxycarbonyl-1-methyl-4 (1H) -quinolone; 3-ethoxycarbonyl-1-ethyl-6-methyl-4 (1H) -quinolone ; 7-ethoxy-3-ethoxycarbonyl-1-ethyl-6-methoxy-4 (1H) -quinolone; 3-ethoxycarbonyl-8-methoxy-4 (1H)- Quinolone; 3-ethoxycarbonyl-8-methoxy-5-methyl-4 (1H) -quinolone; 3-ethoxycarbonyl-8-methoxy-5-phenyl-4 (1H) -quinolone; 8-dimethoxy-3-ethoxycarbonyl-1-ethyl-4 (1H) -quinolone; 3-ethoxycarbonyl-1-ethyl-8-methoxy-6-methylsulfinyl-4 (1H)- Quinolone; 3-ethoxycarbonyl-1-ethyl-8-methoxy-6-methylsulfonyl-4 (1H) quinolone; 6,7-dimethoxy-3-hydroxymethyl-4 (1H) -quinolone; 6,7-dimethoxy-3-hydroxymethyl-1-methyl-4 (1H) -quinolone; 3-carboxyl-1-methyl-5,6,7-trimethoxy-4 (1H) -quinolone; 8-acetyl-4 (1H) -quinolone; 6-cyanomethyl-4 (1H) -quinolone; 6- [2-trans (2,5--dimethoxyphenyl) vinyl] -4 (1H) -quinolone; 7,8-dimethyl-1-ethyl-4 (1H) -quinolone; 7-[(1,3-dioxolan-2-yl) methoxy] -6-methoxy-4 (1H) -quinolone; 6- Methoxy-7-methoxymethoxy-4 (1H) -quinolone; 6-methoxy-7-methyl-4 (1H) -quinolone; 1-ethyl-7-methyl-4 (1H) -quinolone; 1- Ethyl-6-methyl-4 (1H) -quinolone; 1-ethyl-5-hydroxy-8-methyl-4 (1H) -quinolone; 6- (2-hydroxy) ethyl-4 (1H)- Nolon; 6-ethoxycarbonyl-4 (1H) -quinolone; 1-ethyl-8-methoxy-5-phenyl-4 (1H) -quinolone; 7-piperidinyl-4 (1H) -quinolone; 8 -(2-propenyl) -4 (1H) -quinolone; 8- (2-trans-butenyl) -7-hydroxy-6-methoxy-4 (1H) -quinolone; 1-ethyl-6-meth Oxy-4 (1H) -quinolone; 6-ethoxy-1-ethyl-4 (1H) -quinolone ;, 1,6-diethyl-4 (1H) -quinolone; 6-ethoxy-3-ethoxycar Bonyl-8-methoxy-4 (1H) -quinolone; 6-ethoxy-3-ethoxycarbonyl-1-ethyl-8-methoxy-4 (1H) -quinolone; 8-ethoxy-3-e Methoxycarbonyl-1-ethyl-8-methoxy-4 (1H) -quinolone; 5-ethoxy-3-[(2-ethoxy) ethoxycarbonyl-8-methoxy-4 (1H) -quinolone ; 3-ethoxycarbonyl-8-methoxy-4 (1H) -thioquinolone; 7,8-dimethyl-3-ethoxycarbonyl-1-ethyl-4 (1H) -quinolone; 5-acetoxy- 3-ethoxycarbonyl-1-8-methyl-4 (1H) -quinolone; 3-ethoxycarbonyl-8-phenylsulfonyl-4 (1H) -quinolone; 6-diethylamino-3-ethoxy Carbonyl-8-methyl-4 (1H) -quinolone; 1,6-dimethyl-3-ethoxycarbonyl-4 (1H) -quinolone; 3-car Reboxyl-6-ethoxy-1-ethyl-7-methoxy-4 (1H) -quinolone; 3-carboxyl-1-ethyl-5-methyl-4 (1H) -quinolone; 3-carboxy-7 , 8-dimethyl-6-ethoxy-1-ethyl-4 (1H) -quinolone; 3-carboxyl-6-ethoxy-1,7,8-trimethyl-4 (1H) -quinolone; 3-carboxyl -1-ethyl-6-methyl-4 (1H) -quinolone; 3-carboxyl-8-methoxy-5-phenyl-4 (1H) -quinolone; 3-carboxy-7-ethoxy-6-meth Methoxy-1-methyl-4 (1H) quinolone; 3-carboxy-7-ethoxy-6-methoxy-1-n-propyl-4 (1H) -quinolone; 2-cyclopropyl-4 (1H)- Quinolone; 1-ethyl-2- (2-thienyl) -4 (1H) -quinolone; 5-benzyloxy-6-methoxy-2- (3-pyridyl) -4 (1H) -quinolone; 2- (2-thienyl) -4 (1H) -quinolone; 6,7-dimethoxy-3- (4-phenylpiperidinyl) carbonyl-4 (1H) -quinolone; 8-methoxy-5-methyl- 3- (4-phenyllipridinyl) carbonyl-4 (1H) -quinolone; 8-methoxy-1-methyl-3- {1- [4- (3,4-methylenedioxybenzyl) -pipera Genyl] carbonyl-4 (1H) -quinolone; 1-ethyl-3- {1- [4- (2methoxyphenyl) piperazinyl] carbonyl} -6-methyl-4 (1H) -quinolone; 3 -{1- [4- (2-meth Methoxyphenyl) piperazinyl] carbonyl} -6-methyl-4 (1H) -quinolone; 6,7-dimethoxy-1-ethyl-3- {1- [4- (4-nitrophenyl) piperazinyl ] Carbonyl} -4 (1H) -quinolone; 6- [2-trans- (2,5-dimethoxyphenyl) vinyl] -1-ethyl-4 (1H) -quinolone; And 2-cyclopropyl-1-ethyl-4 (1H) -quinolone;

※ 참고사항 : 최초출원내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.