KR960000873A - Novel quinoline carboxylic acid derivatives having 7- (4-amino-3-oxime) pyrrolidine substituents and preparation methods thereof - Google Patents

Novel quinoline carboxylic acid derivatives having 7- (4-amino-3-oxime) pyrrolidine substituents and preparation methods thereof Download PDF

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KR960000873A
KR960000873A KR1019940013603A KR19940013603A KR960000873A KR 960000873 A KR960000873 A KR 960000873A KR 1019940013603 A KR1019940013603 A KR 1019940013603A KR 19940013603 A KR19940013603 A KR 19940013603A KR 960000873 A KR960000873 A KR 960000873A
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amino
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홍창용
김영관
김세호
최훈
장재혁
남두현
곽진환
이용희
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성재갑
주식회사 엘지화학
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • 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
    • A61K31/4353—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 ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/4375—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 ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a six-membered ring having nitrogen as a ring heteroatom, e.g. quinolizines, naphthyridines, berberine, vincamine
    • 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
    • A61K31/4709—Non-condensed quinolines and containing further heterocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/18—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/20—Oxygen atoms
    • C07D215/24—Oxygen atoms attached in position 8
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D215/38—Nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Abstract

본 발명은 퀴놀론 모핵의 7번 위치에 4-아미노-3-옥심피롤리딘계 치환체를 갖는 화합물로서, 우수한 항균작용과 광범위한 항균스펙트럼을 갖는 하기 구조식(I)의 신규한 퀴놀린(또는 나프티리딘) 카르복실산 유도체, 약학적으로 허용가능한 그의 염 및 그의 제조방법에 관한 것이다.The present invention is a compound having a 4-amino-3-oximepyrrolidine-based substituent at position 7 of the quinolone mother nucleus, and has a novel quinoline (or naphthyridine) carbide of formula (I) having excellent antibacterial action and broad antibacterial spectrum. Acid derivatives, pharmaceutically acceptable salts thereof, and methods for preparing the same.

상기식에서 Q는 C-H, C-F, C-C1, C-OH, C-O-메틸, 또는 N이고, R은 수소, 메틸, 또는 아미노이며, R1은 사이클로프로필, 에틸, 1개 이상의 불소원자로 치환된 페닐이고, R2는 수소, C1-4의 직쇄 또는 측쇄 알킬, 페닐 또는 알릴을 나타낸다.Wherein Q is CH, CF, C-C1, C-OH, CO-methyl, or N, R is hydrogen, methyl, or amino, R 1 is cyclopropyl, ethyl, phenyl substituted with one or more fluorine atoms And R 2 represents hydrogen, C 1-4 straight or branched alkyl, phenyl or allyl.

Description

7-(4-아미노-3-옥심)피롤리딘 치환체를 갖는 신규 퀴놀린 카르복실산 유도체 및 그의 제조방법Novel quinoline carboxylic acid derivatives having 7- (4-amino-3-oxime) pyrrolidine substituents and preparation methods thereof

본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음As this is a public information case, the full text was not included.

Claims (14)

하기 일반식(I)의 퀴놀린카르복실산 유도체, 약학적으로 허용가능한 그의 염 및 그의 용매화물.Quinolinecarboxylic acid derivatives of the general formula (I), pharmaceutically acceptable salts thereof and solvates thereof. 상기식에서 Q는 C-H, C-F, C-C1, C-OH, C-O-메틸, 또는 N이고, R은 수소, 메틸, 또는 아미노이며, R1은 사이클로프로필, 에틸, 1개 이상의 불소원자로 치환된 페닐이고, R2는 수소, C1-4의 직쇄 또는 측쇄 알킬, 페닐 또는 알릴을 나타낸다.Wherein Q is CH, CF, C-C1, C-OH, CO-methyl, or N, R is hydrogen, methyl, or amino, R 1 is cyclopropyl, ethyl, phenyl substituted with one or more fluorine atoms And R 2 represents hydrogen, C 1-4 straight or branched alkyl, phenyl or allyl. 제1항에 있어서, Q는 C-H, C-F, C-C1, C-OH, C-O-메틸, 또는 N이고, R은 수소, 메틸, 또는 아미노이며, R1은 사이클로프로필, 에틸, 2,4-디플루오로페닐이고, R2는 수소, 메틸, 에틸, t-부틸, 페닐 또는 알릴인 화합물.The compound of claim 1, wherein Q is CH, CF, C-C 1, C-OH, CO-methyl, or N, R is hydrogen, methyl, or amino, and R 1 is cyclopropyl, ethyl, 2,4- Difluorophenyl and R 2 is hydrogen, methyl, ethyl, t-butyl, phenyl or allyl. 제2항에 있어서, Q는 C-F, C-C1, 또는 N이고, R은 수소이며, R1은 사이클로프로필 또는 2,4-디플루오로페닐이고, R2는 수소, 메틸, 에틸, 또는 알릴인 화합물.The compound of claim 2, wherein Q is CF, C-C1, or N, R is hydrogen, R 1 is cyclopropyl or 2,4-difluorophenyl, and R 2 is hydrogen, methyl, ethyl, or allyl Phosphorus compounds. 하기 일반식(II)의 화합물을 용매중에서 산수용체의 존재하에 하기 일반식(III)의 화합물과 반응시킴을 특징으로 하여 일반식(I)의 화합물을 제조하는 방법.A process for preparing a compound of formula (I), wherein the compound of formula (II) is reacted with a compound of formula (III) in the presence of an acid acceptor in a solvent. 상기식에서, Q, R, R1및 R2는 제1항에서 언급한 바와 같고, X는 할로겐이다.Wherein Q, R, R 1 and R 2 are as mentioned in claim 1 and X is halogen. 제4항에 있어서, 일반식(III)의 화합물은 염산, 브롬산 또는 트리플루오로아세트산과의 염 형태로 사용됨을 특징으로 방법.5. Process according to claim 4, wherein the compound of formula (III) is used in the form of a salt with hydrochloric acid, bromic acid or trifluoroacetic acid. 제4항에 있어서, 일반식(III)의 화합물을 일반식(II)의 화합ㅁ루에 대해 동몰량 내지 1.5 몰배량 사용함을 특징으로 하는 방법.The method according to claim 4, wherein the compound of formula (III) is used in an equimolar amount to 1.5 molar times with respect to the compound of formula (II). 제4항에 있어서, 용매는 아세토니트릴, 디메틸포름아미드, 디메틸설폭시드, 피리딘, 및 헥사메틸포스포아미드 중에서 선택됨을 특징으로 하는 방법.The method of claim 4 wherein the solvent is selected from acetonitrile, dimethylformamide, dimethylsulfoxide, pyridine, and hexamethylphosphoamide. 제4항에 있어서, 산수용체는 무기염기로서 탄산수소나트륨, 탄산칼륨 또는 유기염기로서 트리에틸아민, 디이소프로필에틸아민, 피리딘, N,N-디메틸아닐린, N,N-디메틸아미노피리딘, 1,8-디아자바이사이클로[5,4,0]운데크-7-센, 1,4-디아자바이사이클로[2,2,2]옥탄 중에서 선택됨을 특징으로 하는 방법.The acid acceptor according to claim 4, wherein the acid acceptor is sodium hydrogen carbonate, potassium carbonate as an inorganic base or triethylamine, diisopropylethylamine, pyridine, N, N-dimethylaniline, N, N-dimethylaminopyridine, 1 , 8-diazabicyclo [5,4,0] undec-7-cene, 1,4-diazabicyclo [2,2,2] octane. 제4항에 있어서, 반응 온도가 실온 내지 200℃임을 특징으로 하는 방법.The method of claim 4, wherein the reaction temperature is from room temperature to 200 ° C. 6. 제4항에 있어서, 반응 1 내지 20시간 동안 진행시킴을 특징으로 하는 방법.The method of claim 4, wherein the reaction proceeds for 1 to 20 hours. 제4항에 있어서, 일반식(III)의 화합물은 아미노기가 보호된 하기 일반식(III')의 형태로 반응시키고, 계속하여 아미노 보호기를 제거시킴을 특징으로 하는 방법.The method according to claim 4, wherein the compound of formula (III) is reacted in the form of the following general formula (III ') in which the amino group is protected, and subsequently the amino protecting group is removed. 상기식에서, R2는 제1항에서 언급한 바와 같고, P는 아미노 보호기를 나타낸다.Wherein R 2 is as mentioned in claim 1 and P represents an amino protecting group. 제11항에 있어서, 아미노 보호기는 포르밀, 아세틸, 트리플루오로아세틸, 메톡시카르보닐, 벤질옥시카르보닐, 파라-메톡시벤질옥시카르보닐, 트리틸, 트리메틸실릴, 디페닐포스피닐, 테트라하이드로피라닐임을 특징으로 하는 방법.12. The amino protecting group of claim 11, wherein the amino protecting group is formyl, acetyl, trifluoroacetyl, methoxycarbonyl, benzyloxycarbonyl, para-methoxybenzyloxycarbonyl, trityl, trimethylsilyl, diphenylphosphinyl, tetra Characterized in that it is hydropyranyl. 제1항에 따른 일반식(I)의 화합물을 유효 성분으로 함유함을 특징으로 하는 항균제 조성물.An antimicrobial composition comprising the compound of formula (I) according to claim 1 as an active ingredient. 제13항에 있어서, 일반식(I)의 화합물을 단위 투약량내에 1 내지 100mg 함유람을 특징으로 하는 조성물.The composition according to claim 13, wherein 1 to 100 mg of the compound of formula (I) is contained in a unit dose. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.※ Note: The disclosure is based on the initial application.
KR1019940013603A 1994-06-16 1994-06-16 Novel quinoline carboxylic acid derivatives having 7-(4-amino-3-oxime)pyrrolidine substituent and process for preparing thereof KR0120278B1 (en)

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