KR960004339A - Novel quinoline compounds and preparation method thereof - Google Patents

Novel quinoline compounds and preparation method thereof Download PDF

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KR960004339A
KR960004339A KR1019950018354A KR19950018354A KR960004339A KR 960004339 A KR960004339 A KR 960004339A KR 1019950018354 A KR1019950018354 A KR 1019950018354A KR 19950018354 A KR19950018354 A KR 19950018354A KR 960004339 A KR960004339 A KR 960004339A
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South Korea
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fluoro
salts
oxo
hexane
carboxylic acid
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KR1019950018354A
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Korean (ko)
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문순구
이관순
류의상
문영호
김상태
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임성기
한미약품공업 주식회사
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/47—Quinolines; Isoquinolines

Abstract

본 발명은 종래의 퀴놀린계 항생제에 비해 뛰어난 항균 활성을 갖는 하기 일반식(Ⅰ)의 신규한 퀴놀린계 화합물 및 약제학적으로 허용되는 그의 염에 관한 것이다.The present invention relates to novel quinoline compounds of the general formula (I) and pharmaceutically acceptable salts thereof having superior antibacterial activity compared to conventional quinoline antibiotics.

상기 식에서, R1은 수소 또는 에스테르 형성 그룹이고, R2는 수소, 아미노, 저급알킬아미노, 하이드록시, 저급알콕시, 머캅토, 저급알킬티오 또는 할로겐이며, Z는 하기 일반식의 아민 화합물이고Wherein R 1 is hydrogen or an ester forming group, R 2 is hydrogen, amino, lower alkylamino, hydroxy, lower alkoxy, mercapto, lower alkylthio or halogen, Z is an amine compound of the general formula

(여기서, R3는 수소 또는 저급알킬을 나타내고, R4및 R5는 각각 동일하거나 상이하며 수소 또는 C1-C2알킬을 나타낸다), X는 N 또는 C-C6이다(여기서, R6은 수소, 할로겐, 하이드록시, 메틸, 시아노, 니트로, 또는 메톡시를 나타낸다).Wherein R 3 represents hydrogen or lower alkyl, R 4 and R 5 are the same or different and represent hydrogen or C 1 -C 2 alkyl, respectively, X is N or CC 6 , wherein R 6 is hydrogen, halogen, Hydroxy, methyl, cyano, nitro, or methoxy).

Description

신규한 퀴놀린계 화합물 및 그의 제조방법Novel quinoline compounds and preparation method thereof

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

Claims (10)

하기 일반식(Ⅰ)의 퀴놀계 화합물 및 약제학적으로 허용되는 그의 염.Quinol compounds of the general formula (I) and pharmaceutically acceptable salts thereof. 상기 식에서, R1은 수소 또는 에스테르 형성 그룹이고, R2는 수소, 아미노, 저급알킬아미노, 하이드록시, 저급알콕시, 머캅토, 저급알킬티오 또는 할로겐이며, Z는 하기 일반식의 아민 화합물이고Wherein R 1 is hydrogen or an ester forming group, R 2 is hydrogen, amino, lower alkylamino, hydroxy, lower alkoxy, mercapto, lower alkylthio or halogen, Z is an amine compound of the general formula (여기서, R3는 수소 또는 저급알킬을 나타내고, R4및 R5는 각각 동일하거나 상이하며 수소 또는 C1-C2알킬을 나타낸다), X는 N 또는 C-C6이다(여기서, R6은 수소, 할로겐, 하이드록시, 메틸, 시아노, 니트로, 또는 메톡시를 나타낸다).Wherein R 3 represents hydrogen or lower alkyl, R 4 and R 5 are the same or different and each represents hydrogen or C 1 -C 2 alkyl, and X is N or CC 6 , wherein R 6 is hydrogen , Halogen, hydroxy, methyl, cyano, nitro, or methoxy). 제1항에 있어서, R1은 수소이고, R2는 수소 또는 아미노이며, Z는 하기 일반식의 아민 화합물이고The compound of claim 1, wherein R 1 is hydrogen, R 2 is hydrogen or amino, and Z is an amine compound of the general formula (여기서, R3는 수소 또는 저급알킬을 나타내고, R4및 R5는 각각 동일하거나 상이하며 수소 또는 C1-C2알킬을 나타낸다), X는 N 또는 C-C6(여기서, R6은 수소, 메톡시 또는 할로겐을 나타낸다).(Wherein, R 3 represents hydrogen or lower alkyl, R 4 and R 5 are each the same or different and each represents hydrogen or C 1 -C 2 alkyl), X is N or CC 6 (wherein, R 6 is hydrogen, Methoxy or halogen). 제2항에 있어서, (1) 6,8-디플루오르-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-7-(6-메틸-3,6-디아자비사이클로[3,1,0]헥산-3-일)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (2) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6,8-디플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (3) 6,8-디플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-7-(1-메틸-3,6-디아자비사일클로[3,1,0]헥산-3-일)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (4) 5-아미노-7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6,8-디플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (5) 8-클로로-6-플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-7-(1-메틸-3,6-디아자비사이클로[3,1,0]헥산-3-일)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (6) 8-클로로-7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (7) 8-클로로-7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-(시스-2-플루오로-1-사이클로프로필)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (8) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6,8-디플루오로-1-(시스-2-플루오로-1-사이클로프로필)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (9) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-(시스-2-플루오로-1-사이클로프로필)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (10) 5-아미노-7-(3,6-디아자비비사이클로[3,1,0]헥산-3-일)-6,8-디플루오로-1-(시스-2-플루오로-1-사이클로프로로필)-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (11) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-8-메톡시-4-옥소-1,4-디하이드로퀴놀린-3-카르복실산 및 그의 염; (12) 7-(3,6-디아자비사이클로[3,1,0]헥산-3-일)-6-플루오로-1-[(1R,2S)-2-플루오로-1-사이클로프로필]-4-4-옥소-1,4-디하이드로-1,8-나프티리딘-3-카르복실산 및 그의 염인 화합물.The compound according to claim 2, wherein (1) 6,8-difluoro-1-[(1R, 2S) -2-fluoro-1-cyclopropyl] -7- (6-methyl-3,6-diazabicyclo [3,1,0] hexane-3-yl) -4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (2) 7- (3,6-diazabicyclo [3,1,0] hexane-3-yl) -6,8-difluoro-1-[(1R, 2S) -2-fluoro-1 -Cyclopropyl] -4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (3) 6,8-difluoro-1-[(1R, 2S) -2-fluoro-1-cyclopropyl] -7- (1-methyl-3,6-diazabisyclo [3,1 , 0] hexane-3-yl) -4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (4) 5-amino-7- (3,6-diazabicyclo [3,1,0] hexane-3-yl) -6,8-difluoro-1-[(1R, 2S) -2- Fluoro-1-cyclopropyl] -4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (5) 8-chloro-6-fluoro-1-[(1R, 2S) -2-fluoro-1-cyclopropyl] -7- (1-methyl-3,6-diazabicyclo [3,1 , 0] hexane-3-yl) -4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (6) 8-chloro-7- (3,6-diazabicyclo [3,1,0] hexane-3-yl) -6-fluoro-1-[(1R, 2S) -2-fluoro- 1-cyclopropyl] -4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (7) 8-chloro-7- (3,6-diazabicyclo [3,1,0] hexane-3-yl) -6-fluoro-1- (cis-2-fluoro-1-cyclopropyl ) -4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (8) 7- (3,6-diazabicyclo [3,1,0] hexane-3-yl) -6,8-difluoro-1- (cis-2-fluoro-1-cyclopropyl) 4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (9) 7- (3,6-diazabicyclo [3,1,0] hexane-3-yl) -6-fluoro-1- (cis-2-fluoro-1-cyclopropyl) -4- Oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (10) 5-amino-7- (3,6-diazabibicyclo [3,1,0] hexane-3-yl) -6,8-difluoro-1- (cis-2-fluoro- 1-cycloproprophyll) -4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (11) 7- (3,6-diazabicyclo [3,1,0] hexane-3-yl) -6-fluoro-1-[(1R, 2S) -2-fluoro-1-cyclopropyl ] -8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid and salts thereof; (12) 7- (3,6-diazabicyclo [3,1,0] hexane-3-yl) -6-fluoro-1-[(1R, 2S) -2-fluoro-1-cyclopropyl ] -4-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and salts thereof. 제1항에 있어서, 에스테르 형성 그룹이 저급알킬, C3-C7사이클로알킬 또는 벤질인 화합물.The compound of claim 1, wherein the ester forming group is lower alkyl, C 3 -C 7 cycloalkyl, or benzyl. 제1항에 있어서, 약제학적으로 허용되는 염이 산부가염인 화합물.The compound of claim 1, wherein the pharmaceutically acceptable salt is an acid addition salt. 제5항에 있어서, 산부가염이 젖산염, 메탄설폰산염, 염산염 중에서 선택된 1종인 화합물.The compound according to claim 5, wherein the acid addition salt is one selected from lactate, methanesulfonate and hydrochloride. 하기 일반식(Ⅱ)의 화합물 또는 그의 착화합물을 염기존재하에 하기 일반식(Ⅲ)의 화합물과 반응시킴을 특징으로 하여 하기 일반식(Ⅰ)의 화합물 및 약제학적으로 허용되는 그의 염을 제조하는 방법.A method for preparing the compound of formula (I) and a pharmaceutically acceptable salt thereof, characterized by reacting a compound of formula (II) or a complex thereof with a compound of formula (III) in the presence of a base: . 상기 식에서, R2및 X는 제1항에 언급한 바와 같고, Y는 할로겐을 나타낸다.Wherein R 2 and X are as mentioned in claim 1 and Y represents halogen. 내용 없음No content 내용 없음No content 활성 물질로서 제1항 내지 6항중 어느 한 항에 따른 화합물 또는 약제학적으로 허용되는 그의 염을 적어도 1종 이상 함유함을 특징으로 하는 항균제 조성물.An antimicrobial composition comprising at least one compound according to any one of claims 1 to 6 or a pharmaceutically acceptable salt thereof as an active substance. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019950018354A 1994-07-02 1995-06-29 Novel quinoline compounds and preparation method thereof KR960004339A (en)

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US6875784B2 (en) * 2002-10-09 2005-04-05 Pharmacia & Upjohn Company Antimibicrobial [3.1.0.] bicyclic oxazolidinone derivatives
DE102004035203A1 (en) 2004-07-21 2006-02-16 Bayer Healthcare Ag Substituted quinolones
DE102006005861A1 (en) 2006-02-09 2007-08-23 Aicuris Gmbh & Co. Kg Substituted quinolones III
WO2016054123A1 (en) 2014-09-30 2016-04-07 Lightner Derek Methods of producing heteropolycycles via bis-epoxidation

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AU1161492A (en) * 1991-01-14 1992-08-17 Hanmi Pharmaceutical Co., Ltd. Novel quinolone compounds and processes for preparation thereof
CA2112165C (en) * 1992-12-25 2003-04-08 Makoto Takemura Bicyclic amine derivatives

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