KR880003954A - Tricyclic Compounds, Methods for Making and Uses thereof - Google Patents

Tricyclic Compounds, Methods for Making and Uses thereof Download PDF

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KR880003954A
KR880003954A KR1019870010082A KR870010082A KR880003954A KR 880003954 A KR880003954 A KR 880003954A KR 1019870010082 A KR1019870010082 A KR 1019870010082A KR 870010082 A KR870010082 A KR 870010082A KR 880003954 A KR880003954 A KR 880003954A
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methyl
fluoro
oxo
pyrido
dihydro
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마사히로 아오끼
미야꼬 가마따
다쯔오 오쯔까
노부오 시마
가주떼루 요꼬세
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에프. 호프만-라 롯슈 앤드 캄파니 아크티엔게젤샤프트
쟝-쟈크 오가이, 프리돌린 클라우스너
에프·호프만-라 롯슈 앤드 캄파니 아크티엔게젤샤프트
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    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
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    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles

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트리사이클릭 화합물, 그의 제조방법 및 용도Tricyclic Compounds, Methods for Making and Uses thereof

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

Claims (43)

일반식(I)의 트리사이클릭 화합물, 그의 약제학적으로 허용되는 염, 및 일반식(I)의 화합물 또는 그의 염의 수화물 또는 용매 화합물.Tricyclic compounds of formula (I), pharmaceutically acceptable salts thereof, and hydrates or solvent compounds of compounds of formula (I) or salts thereof. 상기식에서, R1은 수소원자 또는 카복시-보호 라디칼이고; R2는 수소원자이거나, 할로겐 원자로 치환될 수 있는 저급 알킬 라디칼이며; R3및 R4는 독립적으로 수소원자나 하이드록시 라디칼 또는 치환되거나 비치환된 아미노 라디칼로 치환될 수 있는 저급 알킬 라디칼이고; X는 할로겐 원자이며; R5및 R6은 독립적으로 수소원자이거나 하이드록시 라디칼, 저급 알콕시 라디칼 또는 치환되거나 비치환된 아미노 라디칼로 치환될 수 있는 저급 알킬 라디칼이거나; R5및 R6이 인접한 질소원자와 함께, 탄소원자(들)상에 하나 이상의 치환체로 치환될 수 있는 5내지 7원 헤테로 사이클릭 환을 형성할 수 있으며, 이러한 헤테로 사이클릭 환은 추가로 -NR7-, -O-, -S-, -SO-, -SO2- 또는 -NR7-CO-[여기서, R7은 수소원자, 저급알케닐 라디칼, 치환될 수 있는 저급 알킬 또는 아르알킬 라디칼이거나, 일반식(Ⅱ)로 표시되는 라디칼이다.Wherein R 1 is a hydrogen atom or a carboxy-protecting radical; R 2 is a hydrogen atom or a lower alkyl radical which may be substituted with a halogen atom; R 3 and R 4 are independently lower alkyl radicals which may be substituted with a hydrogen atom or a hydroxy radical or a substituted or unsubstituted amino radical; X is a halogen atom; R 5 and R 6 are independently hydrogen atoms or lower alkyl radicals which may be substituted by hydroxy radicals, lower alkoxy radicals or substituted or unsubstituted amino radicals; R 5 and R 6 together with adjacent nitrogen atoms may form a 5 to 7 membered heterocyclic ring which may be substituted with one or more substituents on the carbon atom (s), which heterocyclic ring may further comprise -NR 7- , -O-, -S-, -SO-, -SO 2 -or -NR 7 -CO- [where R 7 is a hydrogen atom, a lower alkenyl radical, a lower alkyl or aralkyl radical which may be substituted Or a radical represented by the general formula (II). -(CH2)nCOR8(Ⅱ)-(CH 2 ) nCOR 8 (II) (여기서, n은 0내지 4이고, R8은 수소원자, 저급알콕시 라디칼이거나, 치환될 수 있는 아미노, 저급 알킬 또는 아릴 라디칼이다)]를 함유할 수 있다.Wherein n is 0 to 4 and R 8 is a hydrogen atom, a lower alkoxy radical or an amino, lower alkyl or aryl radical which may be substituted. 제1항에 있어서, R3및/또는 R4가 치환된 아미노-저급 알킬 라디칼인 경우에, 디-저급 알킬아미노-저급 알킬, 저급 알킬아미노-저급알킬 또는 저급 사이클로알킬아미노-저급 알킬인 화합물.The compound of claim 1, wherein when R 3 and / or R 4 is a substituted amino-lower alkyl radical, it is di-lower alkylamino-lower alkyl, lower alkylamino-lower alkyl or lower cycloalkylamino-lower alkyl. . 제1항 또는 제2항에 있어서, R5및/또는 R6가 치환된 아미노-저급 알킬 라디칼인 경우에 디-저급 알킬아미노-저급 알킬, 저급 알킬아미노-저급알킬 또는 저급 사이클로알킬아미노-저급 알킬인 화합물.3. The di-lower alkylamino-lower alkyl, lower alkylamino-lower alkyl or lower cycloalkylamino-lower according to claim 1, wherein R 5 and / or R 6 are substituted amino-lower alkyl radicals. Compounds that are alkyl. 제1항 또는 제2항에 있어서, R5및/또는 R6가 인접한 질소원자와 함께 탄소원자(들)상에서 하나이상의 치환체로 치환된 5내지 7원 헤테로 사이클인 경우에, 이러한 탄소원자(들)상의 치환체가 하이드록시, 저급 알콕시, 아미노, 저급 알킬아미노, 저급 사이클로알킬아미노, 디-저급 알킬아미노, 저급 알카노일아미노, 벤질옥시카보닐 아미노, 할로겐, 저급 알킬, 아미노-저급 알킬, 저급 알킬아미노-저급 알킬, 저급 사이클로알킬아미노-저급 알킬, 디-저급-알킬아미노-저급 알킬, 저급 알카노일아미노-저급 알킬, 하이드록시-저급 알킬;(아미노, 할로겐, 하이드록시 및/또는 저급 알콕시로 임의 치환된)페닐 및 헤테로 사이클릭환 중에서 선택되는 화합물.3. The carbon atom (s) according to claim 1, wherein R 5 and / or R 6 together with adjacent nitrogen atoms are 5 to 7 membered heterocycles substituted with one or more substituents on the carbon atom (s). Substituents on hydroxy, lower alkoxy, amino, lower alkylamino, lower cycloalkylamino, di-lower alkylamino, lower alkanoylamino, benzyloxycarbonyl amino, halogen, lower alkyl, amino-lower alkyl, lower alkyl Amino-lower alkyl, lower cycloalkylamino-lower alkyl, di-lower-alkylamino-lower alkyl, lower alkanoylamino-lower alkyl, hydroxy-lower alkyl; (amino, halogen, hydroxy and / or lower alkoxy Optionally substituted) phenyl and heterocyclic ring. 제1항 또는 제2항에 있어서, R5및/또는 R6가 인접한 질소원자와 함께 탄소원자(들)상에서 하나이상의 치환체로 치환된 5내지 7원 헤테로 사이클인 경우에, 이러한 탄소원자(들)상의 치환체가 니트로, 아미노, 할로겐 하이드록시 및/또는 저급 알콕시로 임의 치환된 벤질아미노; 및 일반식의 그룹(여기서, R50및 R51은 저급 알킬이거나 질소원자와 함께 5 내지 8원의 포화 N-헤테로 사이클을 나타낸다)중에서 선택되는 화합물.3. The carbon atom (s) according to claim 1, wherein R 5 and / or R 6 together with adjacent nitrogen atoms are 5 to 7 membered heterocycles substituted with one or more substituents on the carbon atom (s). Benzylamino optionally substituted with nitro, amino, halogen hydroxy and / or lower alkoxy; And general formula Wherein R 50 and R 51 are lower alkyl or represent a 5-8 membered saturated N-hetero cycle with a nitrogen atom. 제1항 내지 제5항중 어느 한 항에 있어서, R7이 치환된 저급 알킬 라디칼인 경우에, 하이드록시, 저급 알콕시, 아미노, 저급 알킬아미노, 디-저급 알킬아미노, 할로겐, 카복시 및/또는 설포에 의해 치환된 화합물.6. The compound of claim 1, wherein when R 7 is a substituted lower alkyl radical, hydroxy, lower alkoxy, amino, lower alkylamino, di-lower alkylamino, halogen, carboxy and / or sulfo. Compound substituted by. 제1항 내지 제5항중 어느 한 항에 있어서, R7이 치환된 아르알킬 라디칼인 경우에, 하나 이상의 아미노, 니트로, 저급 알킬아미노, 디-저급 알킬아미노, 할로겐 및/또는 저급 알콕시 그룹(들)에 의해 치환된 화합물.6. The compound of claim 1, wherein when R 7 is a substituted aralkyl radical, one or more amino, nitro, lower alkylamino, di-lower alkylamino, halogen, and / or lower alkoxy group (s). Compound substituted by 제7항에 있어서, 아르알킬 라디칼이 제7항에서 정의환 바와 같이 임의 치환된 벤질인 화합물.8. Compounds according to claim 7, wherein the aralkyl radical is benzyl optionally substituted as defined in claim 7. 제1항 내지 제5항중 어느 한 항에 있어서, R7이 치환된 아미노 라디칼을 갖는 일반식(Ⅱ)의 라디칼인 경우에, R7이 저급 알킬 및/또는 저급 사이클로알킬로 치환된 아미노 라디칼을 갖는 라디칼인 화합물.Of claim 1 to claim 5, any one of, wherein when R 7 is a radical of formula (Ⅱ) having a substituted amino radical, R 7 is an amino radical substituted by lower alkyl and / or lower cycloalkyl, A compound having a radical. 제1항 내지 제5항중 어느 한 항에 있어서, R7이 치환된 저급 알킬 라디칼을 갖는 일반식(Ⅱ)의 라디칼인 경우에, R7이 카복시 및/또는 저급 알콕시카보닐로 치환된 저급 알킬 라디칼을 갖는 라디칼인 화합물.Of claim 1 to claim 5, any one of wherein, R 7 is a case of radicals of the general formula (Ⅱ) having a lower alkyl radical optionally substituted, R 7 is carboxy and / or a lower alkoxycarbonyl lower alkyl substituted by A compound that is a radical having a radical. 제1항 내지 제5항중 어느 한 항에 있어서, R7이 치환된 아릴 라디칼을 갖는 일반식(Ⅱ)의 라디칼인 경우에, R7이 하나이상의 할로겐, 저급 알콕시, 하이드록시, 니트로 및/또는 아미노 그룹(들)으로 치환된 아릴 라디칼을 갖는 라디칼인 화합물.According to claim 1 to claim 5, any one of wherein, R 7 in the case where the radical of formula (Ⅱ) having a substituted aryl radical, R 7 is one or more halogen, lower alkoxy, hydroxy, nitro, and / or A compound that is a radical having an aryl radical substituted with amino group (s). 제11항에 있어서, 아릴 라디칼이 제11항에서 정의한 바와 같이 임의 치환된 페닐인 화합물.12. The compound of claim 11, wherein the aryl radical is optionally substituted phenyl as defined in claim 11. 제1항 내지 제12항중 어느 한 항에 있어서, X가 불소인 화합물.The compound of any one of claims 1-12 wherein X is fluorine. 제1항 내지 제13항중 어느 한 항에 있어서, R1이 수소인 화합물.The compound of any one of claims 1-13, wherein R 1 is hydrogen. 제1항 내지 제14항중 어느 한 항에 있어서, R2가 메틸인 화합물.The compound of any one of claims 1-14 wherein R 2 is methyl. 제1항 내지 제15항중 어느 한 항에 있어서, R3가 수소인 화합물.The compound of any one of claims 1-15, wherein R 3 is hydrogen. 제1항 및 제3항 내지 제16항중 어느 한 항에 있어서, R4가 수소인 화합물.17. The compound of any one of claims 1 and 3-16, wherein R 4 is hydrogen. 제1항, 제2항, 제4항, 및 제13항 내지 제17항중 어느 한 항에 있어서, 그룹 R5R6N-이인 화합물.18. The compound of any of claims 1, 2, 4, and 13-17, wherein group R 5 R 6 N- is Phosphorus compounds. 제1항, 제2항, 제4항, 및 제13항 내지 제17항중 어느 한 항에 있어서, 그룹 R5R6N-이인 화합물.18. The compound of any of claims 1, 2, 4, and 13-17, wherein group R 5 R 6 N- is Phosphorus compounds. 제1항에 있어서, 9-플루오로-3-메틸-10-(4-메틸-1-피페라지닐)-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 또는 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.The compound of claim 1, wherein 9-fluoro-3-methyl-10- (4-methyl-1-piperazinyl) -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1 -ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, or a hydrate or solvate of said compound or said salt. 제1항에 있어서, 9-플루오로-3-메틸-7-옥소-10-(1-피페라지닐)-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 또는 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.The compound of claim 1, wherein 9-fluoro-3-methyl-7-oxo-10- (1-piperazinyl) -2, 3-dihydro-7H-pyrido [3,2,1-ij]- A compound which is 1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, or a hydrate or solvate of said compound or said salt. 제1항에 있어서, 9-플루오로-3-메틸-10-(3-메틸-1-피페라지닐)-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 또는 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.The compound of claim 1, wherein 9-fluoro-3-methyl-10- (3-methyl-1-piperazinyl) -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1 -ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, or a hydrate or solvate of said compound or said salt. 제1항에 있어서, 9-플루오로-3-메틸-7-옥소-10-(3-페닐-1-피페라지닐)-2,3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 또는 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.The compound of claim 1, wherein 9-fluoro-3-methyl-7-oxo-10- (3-phenyl-1-piperazinyl) -2,3-dihydro-7H-pyrido [3,2,1 -ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, or a hydrate or solvate of said compound or said salt. 제1항에 있어서, 9-플루오로-3-메틸-10-모르폴리노-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 9-플루오로-3-메틸-10-[3-[(메틸아미노)메틸]-1-피롤리디닐]-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-(에틸아미노)-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(3, 4-디메틸-1-피페라지닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 9-플루오로-10-(3-메톡시-1-피롤리디닐)-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 9-플루오로-3-메틸-7-옥소-10-[4-(3-옥소-n-부틸)-1-피페라지닐]-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 디나트륨 9-플루오로-3-메틸-7-옥소-10-[4-(술포나토메틸)-1-피페라지닐]-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실레이트, 10-[3-(아미노메틸)-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-(1-이미다졸릴)-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(4-에틸-1-피페라지닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 9-플루오로-10-[4-(2-하이드록시에틸)-1-피페라지닐]-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 9-플루오로-3-메틸-10-(4-메틸-1-이미다졸릴)-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-10-[3-메틸-4-[(메틸아미노)메틸]-1-피롤리디닐]-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-(아미노메틸)-4-메틸-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-[(에틸아미노)메틸]-4-메틸-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-(아미노메틸)4-클로로-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-(아미노메틸)-4-플루오로-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-클로로-4-[(메틸아미노)메틸]-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-[3-플루오로-4-[(메틸아미노)메틸]-1-피롤리디닐]-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-클로로-4-[(에틸아미노)메틸]-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-[(에틸아미노)메틸]-4-플루오로-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(3-아미노-4-메톡시-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-[3-메톡시-4-(메틸아미노)-1-피롤리디닐]-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-(에틸아미노)-4-메톡시-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-(3-하이드록시-4-메톡시-1-피롤리디닐)-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(3-아미노-4-클로로-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(3-아미노-4-플루오로-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-클로로-4-(메틸아미노)-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-[3-플루오로-4-(메틸아미노)-1-피롤리디닐]-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[4-(아미노메틸)-1-피페리딜]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-(4-하이드록시-1-피페리딜)-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-7-옥소-10-[4-(1-피롤린)-1-피페리딜]-2, 3-디하이드로-7H-피리도[3, 2, 1-ij]-1, 3, 4-벤즈옥사디아진-6-카복실산, 9-플루오로-10-(1-호모피페라지닐)-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-(3-하이드록시-1-피롤리디닐)-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-7-옥소-10-(4-n-프로필-1-피페라지닐)-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-[4-(2-플루오로에틸)-1-피페라지닐]-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[4-(카복시메틸)-1-피페라지닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(4-알릴-1-피페라지닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(1-옥사이드-4-티오모르폴리닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-10-[1-옥사이드-4-티오모르폴리닐)-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(3-클로로-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-(2-플루오로에틸)-10-(4-메틸-1-피페라지닐)-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(4-아미노-1-피페리딜)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-10-[4-(메틸아미노)-1-피페리딜]-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[4-(에틸아미노-1-피페리딜]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-[(에틸메틸아미노)메틸]-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(3-아미노-4-하이드록시-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-[3-하이드록시-4-(메틸아미노)-1-피롤리디닐]-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-7-옥소-10-(4-티오모르폴리닐)-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(2, 6-디메틸-4-모르폴리닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-(아세틸아미노메틸)-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[[2-(디메틸아미노)에틸]메틸아미노]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-7-옥소-10-(3-옥소-1-피페라지닐)-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-2-(하이드록시메틸)-3-메틸-10-(4-메틸-1-피페라지닐)-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 2-[(디메틸아미노)메틸]-9-플루오로-3-메틸-10-(4-메틸-1-피페라지닐)-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[3-(벤질옥시카보닐아미노)-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-7-옥소-10-(4-펜아실-1-피페라지닐)-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-3-메틸-10-[4-(4-니트로벤질)-1-피페라지닐]-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-[4-(3-카복시프로피오닐)-1-피페라지닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(4-아세틸-1-피페라지닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-10-(4-메톡시-1-피페리딜)-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-2, 3-디메틸-10-(4-메틸-1-피페라지닐)-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, -9-플루오로-2, 3-디메틸-7-옥소-10-(1-피페라지닐)-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산,The compound of claim 1, wherein 9-fluoro-3-methyl-10-morpholino-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3, 4-Benzoxadiazine-6-carboxylic acid, 9-fluoro-3-methyl-10- [3-[(methylamino) methyl] -1-pyrrolidinyl] -7-oxo-2, 3-dihydro -7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- [3- (ethylamino) -1-pyrrolidinyl] -9-fluor Rho-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- (3 , 4-dimethyl-1-piperazinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3, 4-Benzoxadiazine-6-carboxylic acid, 9-fluoro-10- (3-methoxy-1-pyrrolidinyl) -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-Benzoxadiazine-6-carboxylic acid, 9-fluoro-3-methyl-7-oxo-10- [4- (3-oxo-n- Butyl) -1-piperazinyl] -2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, disodium 9- Influenza Oro-3-methyl-7-oxo-10- [4- (sulfonatomethyl) -1-piperazinyl] -2,3-dihydro-7H-pyrido [3,2,1-ij] -1 , 3,4-benzoxadiazine-6-carboxylate, 10- [3- (aminomethyl) -1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-di Hydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-10- (1-imidazolyl) -3-methyl -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- (4-ethyl-1- Piperazinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin- 6-carboxylic acid, 9-fluoro-10- [4- (2-hydroxyethyl) -1-piperazinyl] -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3 , 2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 9-fluoro-3-methyl-10- (4-methyl-1-imidazolyl) -7-oxo- 2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-3-methyl-10- [3 -Methyl-4-[(methyl Amino) methyl] -1-pyrrolidinyl] -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6- Carboxylic acid, 10- [3- (aminomethyl) -4-methyl-1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3, 2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- [3-[(ethylamino) methyl] -4-methyl-1-pyrrolidinyl] -9-fluoro -3-methyl-7-oxo-2,3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, 10- [3- (Aminomethyl) 4-chloro-1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1 , 3,4-benzoxadiazine-6-carboxylic acid, 10- [3- (aminomethyl) -4-fluoro-1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2 , 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- [3-chloro-4-[(methylamino) methyl ] -1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benz Oksa Diazine-6-carboxylic acid, -9-fluoro-10- [3-fluoro-4-[(methylamino) methyl] -1-pyrrolidinyl] -3-methyl-7-oxo-2, 3- Dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- [3-chloro-4-[(ethylamino) methyl] -1 -Pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazazine -6-carboxylic acid, 10- [3-[(ethylamino) methyl] -4-fluoro-1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro- 7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- (3-amino-4-methoxy-1-pyrrolidinyl) -9- Fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, -9- Fluoro-10- [3-methoxy-4- (methylamino) -1-pyrrolidinyl] -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1 -ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- [3- (ethylamino) -4-methoxy-1-pyrrolidinyl] -9-fluoro- 3-Methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro- 10- (3-hydroxy-4-methoxy-1-pyrrolidinyl) -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1 , 3,4-benzoxadiazine-6-carboxylic acid, 10- (3-amino-4-chloro-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-di Hydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- (3-amino-4-fluoro-1-pyrrolidinyl)- 9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, 10 -[3-chloro-4- (methylamino) -1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1 -ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-10- [3-fluoro-4- (methylamino) -1-pyrrolidinyl] -3-methyl -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- [4- (aminomethyl) - 1-piperidyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadia Jin-6-carboxylic acid, -9-fluoro-10- (4-hydroxy-1-piperidyl) -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2 , 1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-3-methyl-7-oxo-10- [4- (1-pyrroline) -1-pi Ferridyl] -2, 3-dihydro-7H-pyrido [3, 2, 1-ij] -1, 3, 4-benzoxadiazin-6-carboxylic acid, 9-fluoro-10- (1- Homopiperazinyl) -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-10- (3-hydroxy-1-pyrrolidinyl) -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij]- 1,3,4-benzoxadiazin-6-carboxylic acid, -9-fluoro-3-methyl-7-oxo-10- (4-n-propyl-1-piperazinyl) -2, 3-di Hydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-10- [4- (2-fluoroethyl)- 1-piperazinyl] -3-meth Tyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- [4- (carboxymethyl ) -1-piperazinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benz Oxadiazine-6-carboxylic acid, 10- (4-allyl-1-piperazinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2 , 1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- (1-oxide-4-thiomorpholinyl) -9-fluoro-3-methyl-7-oxo-2 , 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-3-methyl-10- [1- Oxide-4-thiomorpholinyl) -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- (3-chloro-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1, 3,4-Benzoxadiazine-6-carboxylic acid, -9-fluoro-3- (2-fluoroethyl) -10- (4-methyl-1-piperazinyl) -7-oxo-2, 3 Diha Dro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, 10- (4-amino-1-piperidyl) -9-fluoro- 3-Methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro- 3-methyl-10- [4- (methylamino) -1-piperidyl] -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3, 4-Benzoxadiazine-6-carboxylic acid, 10- [4- (ethylamino-1-piperidyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyri Fig. [3,2,1-ij] -1,3,4-Benzoxadiazine-6-carboxylic acid, 10- [3-[(ethylmethylamino) methyl] -1-pyrrolidinyl] -9-fluor Rho-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- (3 -Amino-4-hydroxy-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1 , 3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-10- [3-hydroxy-4- (methylamino) -1-pyrrolidinyl] -3-methyl-7-oxo- 2, 3-Dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-3-methyl-7-oxo-10- (4-thiomorpholinyl) -2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, 10- (2, 6-dimethyl-4-morpholinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4 -Benzoxadiazine-6-carboxylic acid, 10- [3- (acetylaminomethyl) -1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H- Pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10-[[2- (dimethylamino) ethyl] methylamino] -9-fluoro-3- Methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-3- Methyl-7-oxo-10- (3-oxo-1-piperazinyl) -2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadia Jin-6-carboxylic acid, -9-fluoro-2- (hydroxymethyl) -3-methyl-10- (4-methyl-1-piperazinyl) -7-oxo-2, 3-dihi Dro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 2-[(dimethylamino) methyl] -9-fluoro-3-methyl- 10- (4-methyl-1-piperazinyl) -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin- 6-carboxylic acid, 10- [3- (benzyloxycarbonylamino) -1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3 , 2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-3-methyl-7-oxo-10- (4-phenacyl-1-piperazinyl ) -2,3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-3-methyl-10- [4- (4-nitrobenzyl) -1-piperazinyl] -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxa Diazine-6-carboxylic acid, 10- [4- (3-carboxypropionyl) -1-piperazinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyri Fig. [3,2,1-ij] -1,3,4-Benzoxadiazine-6-carboxylic acid, 10- (4-acetyl-1-piperazinyl) -9-fluoro-3-methyl-7 -jade Sub-2,3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-10- (4-meth Methoxy-1-piperidyl) -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6 -Carboxylic acid, -9-fluoro-2, 3-dimethyl-10- (4-methyl-1-piperazinyl) -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1 -ij] -1,3,4-benzoxadiazine-6-carboxylic acid, -9-fluoro-2, 3-dimethyl-7-oxo-10- (1-piperazinyl) -2, 3-di Hydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 에틸 10-[3-(벤질옥시카보닐아미노)-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실레이트, 에틸 10-(3-아미노-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실레이트, 벤질 9-플루오로-10-(3-하이드록시-1-피롤리디닐)-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실레이트,Ethyl 10- [3- (benzyloxycarbonylamino) -1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2, 1-ij] -1,3,4-benzoxadiazine-6-carboxylate, ethyl 10- (3-amino-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2 , 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylate, benzyl 9-fluoro-10- (3-hydroxy- 1-pyrrolidinyl) -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxyl Rate, 벤질 10-(3-클로로-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실레이트, 피발로일옥시메틸 10-[3-(벤질옥시카보닐아미노)-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실레이트, 피발로일옥시메틸 10-(3-아미노-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실레이트, 10-[3-[(4-아미노벤질)아미노]-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산,Benzyl 10- (3-chloro-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1 , 3,4-benzoxadiazine-6-carboxylate, pivaloyloxymethyl 10- [3- (benzyloxycarbonylamino) -1-pyrrolidinyl] -9-fluoro-3-methyl-7 -Oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylate, pivaloyloxymethyl 10- (3- Amino-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benz Oxadiazine-6-carboxylate, 10- [3-[(4-aminobenzyl) amino] -1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro -7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 9-플루오로-10-[3-[[(디메틸아미노)메틸렌]아미노]-1-피롤리디닐]-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 9-플루오로-3-메틸-10-[3-(4-메틸-1-피페라지닐)-1-피롤리디닐]-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(3-아미노-3-메틸-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(트란스-3-아미노-4-페닐-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산,9-fluoro-10- [3-[[(dimethylamino) methylene] amino] -1-pyrrolidinyl] -3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3, 2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 9-fluoro-3-methyl-10- [3- (4-methyl-1-piperazinyl) -1- Pyrrolidinyl] -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, 10- (3- Amino-3-methyl-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3 , 4-Benzoxadiazine-6-carboxylic acid, 10- (trans-3-amino-4-phenyl-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-di Hydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 9-플루오로-3-메틸-10-[3-메틸-3-[(메틸아미노)메틸]-1-피롤리디닐]-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 9-플루오로-3-메틸-10-[트란스-3-[(메틸아미노)메틸]-4-페닐-1-피롤리디닐]-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산, 10-(트란스-3-아미노-4-하이드록시-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산 중에서 선택된 화합물, 그의 약제학적으로 허용되는염, 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.9-fluoro-3-methyl-10- [3-methyl-3-[(methylamino) methyl] -1-pyrrolidinyl] -7-oxo-2, 3-dihydro-7H-pyrido [3 , 2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 9-fluoro-3-methyl-10- [trans-3-[(methylamino) methyl] -4-phenyl -1-pyrrolidinyl] -7-oxo-2, 3-dihydro-7H-pyrido [3,2,1-ij] -1,3,4-benzoxadiazine-6-carboxylic acid, 10- (Trans-3-amino-4-hydroxy-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1- ij] -1,3,4-benzoxadiazine-6-carboxylic acid, a pharmaceutically acceptable salt thereof, the compound or a hydrate or solvent compound of the salt. 제1항에 있어서, 10-[3-[(에틸아미노)메틸]-1-피롤리디닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 또는 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.10- [3-[(ethylamino) methyl] -1-pyrrolidinyl] -9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido according to claim 1 A compound which is [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, or the compound or a hydrate or solvent compound of the salt. 제1항에 있어서, 10-(3-아미노-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.The compound of claim 1, wherein 10- (3-amino-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [3,2,1 -ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, the compound or a hydrate or solvent compound of the salt. 제1항에 있어서, 9-플루오로-3-메틸-10-[3-(메틸아미노)-1-피롤리디닐]-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.The compound of claim 1, wherein 9-fluoro-3-methyl-10- [3- (methylamino) -1-pyrrolidinyl] -7-oxo-2, 3-dihydro-7H-pyrido [3, 2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, the compound or a hydrate or solvent compound thereof. 제1항에 있어서, 10-[4-(4-아미노벤질)-1-피페라지닐]-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.The compound of claim 1, wherein 10- [4- (4-aminobenzyl) -1-piperazinyl] -9-fluoro-3-methyl-7-oxo-2, 3-dihydro-7H-pyrido [ 3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, the compound or a hydrate or solvent compound thereof. 제1항에 있어서, 10-(트란스-3-아미노-4-메틸-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.10- (trans-3-amino-4-methyl-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido according to claim 1 A compound which is [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, the compound or a hydrate or solvent compound thereof. 제1항에 있어서, 10-(트란스-3-아미노-4-메톡시-1-피롤리디닐)-9-플루오로-3-메틸-7-옥소-2, 3-디하이드로-7H-피리도[3,2,1-ij]-1,3,4-벤즈옥사디아진-6-카복실산인 화합물, 그의 약제학적으로 허용되는 염, 상기 화합물 또는 상기 염의 수화물 또는 용매 화합물.10- (trans-3-amino-4-methoxy-1-pyrrolidinyl) -9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyriy according to claim 1 A compound which is also [3,2,1-ij] -1,3,4-benzoxadiazin-6-carboxylic acid, a pharmaceutically acceptable salt thereof, the compound or a hydrate or solvent compound thereof. 일반식(Ⅲ)의 화합물.Compound of general formula (III). 상기식에서, R1은 수소원자 또는 카복시-보호 라디칼이고; R2는 수소원자이거나 할로겐 원자로 치환될 수 있는 저급 알킬 라디칼이며; R3및 R4는 독립적으로 수소원자이거나 하이드록시 라디칼 또는 치환되거나 비치환된 아미노 라디칼로 치환될 수 있는 저급 알킬 라디칼이고; X 및 X'는 동일하거나 상이하며, 할로겐 원자이다.Wherein R 1 is a hydrogen atom or a carboxy-protecting radical; R 2 is a lower alkyl radical which may be hydrogen atom or substituted with halogen atom; R 3 and R 4 are independently a hydrogen atom or a lower alkyl radical which may be substituted with a hydroxy radical or a substituted or unsubstituted amino radical; X and X 'are the same or different and are halogen atoms. 일반식(Ⅴ)의 화합물.Compound of formula (V). 상기식에서, R1은 수소원자 또는 카복시-보호 라디칼이고; R2는 수소원자이거나 할로겐 원자로 치환될 수 있는 저급 알킬 라디칼이며; X는 할로겐이고; R5및 R6은 독립적으로 하이드록시 라디칼, 저급 알콕시 라디칼 또는 치환되거나 비치환된 아미노라디칼로 치환돌 수 있는 저급 알킬 라디칼이거나, R5및 R6는 인접한 질소원자와 함께, 탄소원자(들)상에서 하나이상의 치환체로 치환될 수 있는 5 내지 7원 헤테로 사이클릭 환을 형성할 수 있으며, 이러한 헤테로 사이클릭 환은 추가로 -NR7-, -O-, -S-, -SO-, -SO2- 또는 -NR7-CO-[여기서, R7은 수소원자, 저급 알케닐 라디칼, 치환될 수 있는 저급 알킬 또는 아르알킬 라디칼이거나, 일반식(Ⅱ)로 표시되는 라디칼이다.Wherein R 1 is a hydrogen atom or a carboxy-protecting radical; R 2 is a lower alkyl radical which may be hydrogen atom or substituted with halogen atom; X is halogen; R 5 and R 6 are independently lower alkyl radicals which may be substituted with hydroxy radicals, lower alkoxy radicals or substituted or unsubstituted amino radicals, or R 5 and R 6 together with adjacent nitrogen atoms, carbon atom (s) To form a 5-7 membered heterocyclic ring which may be substituted with one or more substituents on the phase, which heterocyclic ring may further comprise -NR 7- , -O-, -S-, -SO-, -SO 2 -Or -NR 7 -CO- [wherein R 7 is a hydrogen atom, a lower alkenyl radical, a lower alkyl or aralkyl radical which may be substituted, or a radical represented by formula (II). -(CH2)nCOR9(Ⅱ)-(CH 2 ) nCOR 9 (II) (여기서, n은 0 내지 4이고, R8은 수소원자, 저급 알콕시 라디칼이거나, 치환될 수 있는 아미노, 저급 알킬 또는 아릴 라디칼이다)]를 함유할 수 있다.Wherein n is 0 to 4 and R 8 is a hydrogen atom, a lower alkoxy radical, or an amino, lower alkyl or aryl radical which may be substituted. 제1항 내지 제30항중 어느 한 항에서 정의된, 약제학적 활성 물질로서의화합물.A compound as a pharmaceutically active substance as defined in any one of claims 1 to 30. 제1항 내지 제30항중 어느 한 항에서 정의된, 감염성 질환의 치료 및 예방을 위한 약제학적 활성 물질로서의 화합물.A compound as pharmaceutically active substance for the treatment and prevention of an infectious disease as defined in any one of claims 1 to 30. (a) 일반식(Ⅲ)의 화합물(여기서, 존재하는 아미노, 하이드록시 및/또는 카복시 그룹은 보호될 수 있다)을 일반식(Ⅳ)의 아민과 반응 시킨 다음, 필요에 따라 보호 라디칼을 제거하거나; (b) 일반식(Ⅴ)의 화합물(여기서, 존재하는 아미노, 하이드록시 및/또는 카복시 그룹은 보호될 수 있다)을 일반식(Ⅵ)의 카보닐 화합물 또는 그의 중합체, 아세탈, 케탈 또는 엔올 에테르와 반응시킨다음, 필요에 따라서 보호 라디칼을 제거하거나; (c) R7이 수소가 아닌 일반식(Ⅰ)의 화합물을 제조하기 위해 R7이 수소인 일반식(Ⅰ)의 화합물을 R70(R70은 R7에 대하여 정의한 바와 같으나, 단 수소가 아니다)을 생성하는 시약과 반응시키거나; (d) R5및/또는 R6이 저급 알킬인(또는 디-저급 알킬아미노 또는 저급 알콕시 그룹을 함유하는)일반식(Ⅰ)의 화합물을 제조하기 위해 R5및/또는 R6이 수소이거나 아미노, 저급 알킬아미노 또는 하이드록시 그룹을 함유하는 일반식(Ⅰ)의 화합물을 저급 알킬화시키거나; (e) R5R6N-이 -SO- 또는 -SO2-를 갖는 5 내지 7원 헤테로 사이클릭 환인 일반식(Ⅰ)의 화합물을 제조하기 위해 헤테로 사이클릭 환이 -S-를 함유하는 상응하는 화합물을 산화시키거나, (f) 유리 아미노, 하이드록시 및/또는 카복시 그룹을 갖는 상응하는 일반식(Ⅰ)의 화합물을 제조하기 위해 보호된 아미노, 하이드록시 및/또는 카복시 그룹을 갖는 일반식(Ⅰ)의 화합물로부터 보호 그룹(들)을 제거하거나, (g) 할로겐원자를 함유하는 일반식(Ⅰ)의 화합물을 제조하기 위해 R1이 카복시-보호 라디칼인 상응하게 하이드록시-치환된 일반식(Ⅰ)의 화합물을 할로겐화시키고, 경우에 따라, 상기의 보호 라디칼 R1을 제거하거나; (h) 아미노 그룹을 함유하는 일반식(Ⅰ)의 화합물을 제조하기 위해 상응하게 니트로-치환된 일반식(Ⅰ)화합물의 니트로 그룹을 환원시키거나; (i) 일반식그룹을 함유하는 일반식(Ⅰ)의 화합물을 제조하기 위해 상응하게 아미노-치환된 일반식(Ⅰ)화합물의 아미노 그룹을 하기 일반식(Ⅶ)의 포름아미드 유도체의 반응성 유도체와 반응시키거나, (j) R1이 카복시-보호라디칼인 일반식(Ⅰ)의 화합물을 제조하기 위해 일반식(Ⅰ)의 카복실산을 상응하게 에스테르화시키거나, (k) 일반식(Ⅰ) 화합물의 약제학적으로 허용되는 염, 수화물 또는 용매 화합물 또는 이러한 염의 수화물 또는 용매 화합물을 제조하기 위한 일반식(I)의 화합물을 그의 염, 수화물 또는 용매 화합물로 전환시키거나 그의 염의 수화물 또는 용매 화합물로 전환시킴을 특징으로 하여 제1항 내지 제30항중 어느 한 항에 따른 화합물을 제조하는 방법.(a) reacting a compound of general formula (III), wherein the amino, hydroxy and / or carboxyl groups present may be protected) with an amine of general formula (IV) and then do or; (b) a compound of formula (V), wherein the amino, hydroxy and / or carboxyl groups present may be protected) a carbonyl compound of formula (VI) or a polymer thereof, acetal, ketal or enol ether React with and, as necessary, remove the protective radicals; (c) R 7 is gateuna a compound of formula (Ⅰ) R 7 is hydrogen to produce a compound represented by the general formula (Ⅰ) other than hydrogen as defined with respect to R 70 (R 70 is R 7, only hydrogen is Or react with the reagents that produce it); (d) R 5 and / or R 6 is lower alkyl, - to prepare the compounds of (or di-lower alkylamino or containing a lower alkoxy group) Formula (Ⅰ) R 5 and / or R 6 is hydrogen or Lower alkylation of a compound of formula (I) containing amino, lower alkylamino or hydroxy groups; (e) Corresponding heterocyclic rings containing -S- to prepare compounds of formula (I) wherein R 5 R 6 N- is a 5-7 membered heterocyclic ring having -SO- or -SO 2- To oxidize a compound or (f) to prepare a corresponding compound of formula (I) having free amino, hydroxy and / or carboxyl groups, with a protected amino, hydroxy and / or carboxyl group. A corresponding hydroxy-substituted general in which R 1 is a carboxy-protecting radical to remove the protecting group (s) from the compound of (I) or (g) to prepare a compound of formula (I) containing a halogen atom Halogenating the compound of formula (I), optionally removing said protective radical R 1 ; (h) reducing the nitro group of the corresponding nitro-substituted general formula (I) compound to produce a compound of general formula (I) containing an amino group; (i) general formula Reacting the amino group of the corresponding amino-substituted general formula (I) compound with the reactive derivative of the formamide derivative of the following general formula (VII) to prepare a compound of general formula (I) containing a group ( j) correspondingly esterifying the carboxylic acid of formula (I) to prepare a compound of formula (I) wherein R 1 is a carboxy-protecting radical, or (k) a pharmaceutically acceptable compound of formula (I) Characterized by converting the resulting salt, hydrate or solvate compound or a compound of formula (I) to prepare a hydrate or solvate of such salt to its salt, hydrate or solvate or to its hydrate or solvate. 31. A process for preparing a compound according to any one of claims 1-30. 상기식에서, R1내지 R6및 X는 제1항에서 정의한 바와 같으며, X'는 할로겐 원자이고, R50및 R51은 저급 알킬이거나, 질소원자와 함께 5 내지 8원의 포화 N-헤테로사이클을 나타낸다.Wherein R 1 to R 6 and X are as defined in claim 1, X 'is a halogen atom, R 50 and R 5 1 are lower alkyl or a 5-8 membered saturated N-hetero with a nitrogen atom Indicates a cycle. 제35항에 있어서, 공정(a) 내지 (h), (j) 및 (k)중 하나를 수행하는 방법.36. The method of claim 35, wherein one of the processes (a) to (h), (j), and (k) is performed. 제1항 내지 제30항중 어느 한 항에 따른 화합물을 함유하는 약제학적 제제.A pharmaceutical formulation containing a compound according to any one of claims 1 to 30. 감염성 질환의 치료 및 예방을 위한, 제1항 내지 제30항중 어느 한 항에 따른 화합물을 함유하는 약제학적 제제.A pharmaceutical formulation containing a compound according to any one of claims 1 to 30 for the treatment and prevention of infectious diseases. 제1항 내지 제30항중 어느 한 항에 따른 화합물의 질환의 치료 및 예방을 위한 것으로서의 용도.Use of a compound according to any one of claims 1 to 30 for the treatment and prevention of a disease. 제1항 내지 제30항중 어느 한 항에 따른 화합물의 감염성 질환의 치료 및 예방을 위한 것으로서의 용도.Use of a compound according to any one of claims 1 to 30 for the treatment and prevention of an infectious disease. 제1항 내지 제30항중 어느 한 항에 따른 화합물의 감염성 질환의 치료 및 예방을 위한 약제의 제조를 위한 것으로서의 용도.Use of a compound according to any one of claims 1 to 30 for the manufacture of a medicament for the treatment and prevention of an infectious disease. 제1항 내지 제30항중 어느 한 항에 있어서, 제35항에 청구된 방법 또는 화학적으로 그와 명백히 대등한 방법에 따라 제조된 화합물.31. A compound according to any one of claims 1 to 30, prepared according to the method as claimed in claim 35 or in a chemically comparable manner. 본 명세서에 기술된 신규 화합물, 제조 공정 및 방법.Novel compounds, preparation processes and methods described herein. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
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FI873940A0 (en) 1987-09-11
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IL83814A (en) 1991-09-16
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PH23930A (en) 1990-01-23
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ZW16387A1 (en) 1988-05-25
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NO169125B (en) 1992-02-03
KR960002857B1 (en) 1996-02-27
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FI86428C (en) 1992-08-25
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NO169125C (en) 1992-05-13
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