KR890003704A - 7-치환체의 측쇄에 α- 아미노산을 포함하는 퀴놀른 및 나프티리딘 항균제 - Google Patents

7-치환체의 측쇄에 α- 아미노산을 포함하는 퀴놀른 및 나프티리딘 항균제 Download PDF

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KR890003704A
KR890003704A KR1019880010617A KR880010617A KR890003704A KR 890003704 A KR890003704 A KR 890003704A KR 1019880010617 A KR1019880010617 A KR 1019880010617A KR 880010617 A KR880010617 A KR 880010617A KR 890003704 A KR890003704 A KR 890003704A
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compound
amino
cyclopropyl
oxo
pyrrolidinyl
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피터 산체스 죠셉
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크리스틴 에이.트라우트웨인
워너 램버트 컴퍼니
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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
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    • 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
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    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
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Abstract

내용 없음

Description

7-치환체의 측소에- 아미노산을 포함하는 퀴놀른 및 나프티리딘 항균제
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (41)

  1. 다음 구조식의 화합물, 이것의 광학 활성 이성체 또는 제약학적으로 허용가능한 산 부가염.
    식중, X는 N, CH, CF, CCI, CCF3, COR2또는 CNR2R3, ; Y는 H, F, NH2, 또는 OR2; Z는
    R는 H,C1-6알킬 또는 양이온; R1는 C1-6알킬, 알킬이 C1-4비닐, C3-6사이클로알킬, 아릴 또는 할로겐, 하이드록시, 아미노나 C1-4알킬로 치환된 아릴을 가지는 할로알킬; R2및 R3는 각각 독립적으로 수소 또는 C1-4알킬; R4는 n이 0,1 또는 2인 -(CR2R3)n-NR2R5; 및 R5는R6가 OR2, NR2R3,CO2H, CO2R2,CONR2R3,, 아릴, 또는 할로겐, 하이드록시, 아미노나, C1-4알킬로 치환된 아릴로 치환된 C1-10알킬, 또는 페닐, p- 하이드록시페닐, 또는-아미노그룹의 질소와 함께 트리메틸렌이나 하이드록시 치환된 트리메틸렌인임.
  2. 제1항에 있어서, R6가 OR2,NR2R3,CO2H, CO2R2,CONR2R3, , SR2,SS-CH2 , -CN, 페닐, 할로겐, 하이드록시, 아미노나 C1-4알킬로 치환된 페닐로 치환된 C1-10알킬, 수소, 또는 C1-10알킬, 3-인돌이나 또는 적어도 하나의 질소, 산소 또는 황 원자를 포함하는 5- 나 6- 원의 복소환, 또는 페닐,p-하이드록시페닐, 또는 아미노 그룹의 질소원자와 함께 트리메틸렌이나 하이드록시치환된 트리메틸렌인 화합물.
  3. 제2항에 있어서, R6가 OH NH2,CO2H, CONH2, , SR2,, 페닐, p-하이드록시페닐, 3-인돌일, 4-이미다졸일로 치환된 C1-4알킬, 수소, C1-4알킬, 또는 페닐,p-하이드록시페닐이거나 또는-아미노 그룹의 질소와 함게 트리메틸렌이나 하이드록시 치환된 트리메틸렌인 화합물.
  4. 제3항에 있어서, R1이 C1-3알킬, 2-플루오로에틸, 비닐, 시클로프로필, 페닐, 할로겐, 하이드록시, 아미노나 C1-4알킬로 치환된 페닐, 또는 적어도 하나의 질소, 산소나 황 원자를 포함하는 5- 또는 6- 원의 복소환인 화합물.
  5. 제4항에 있어서, X가 N, CH, CF, CCI, 또는 CCF3인 화합물.
  6. 제5항에 있어서, Y가 H 또는 NH2인 화합물.
  7. 제6항에 있어서, R1이 에틸, 2-플루오로에틸, 비닐, 또는 시클로프로필인 화합물.
  8. 제7항에 있어서, Z가
    인 화합물.
  9. 제7항에 있어서, E가
    인 화합물.
  10. 제7항에 있어서, Z가
    인 화합물.
  11. 제8항에 있어서, Z가이고 R1이 시클로프로필인 화합물.
  12. 제11항에 있어서, 7-[3-[(2-아미노-1-옥소프로필)아미노]-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  13. 제12항 화합물의 [S-(R*,R*)] 또는 [S-(R*,R*)]이성체.
  14. 제11항에 있어서, 7-[3-[[(아미노아세틸)아미노]-1-피롤리딘일-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 그것의 광학 이성체인 화합물.
  15. 제11항에 있어서, 7-[3-[[(2-아미노-1-옥소-3-페닐프로필)아미노-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  16. 제15항 화합물의 [S-(R*,R*)]또는 [S-(R*,R*)] 이성체
  17. 제11항에 있어서, 7-[3-[2,5-디아미노-1,5-디옥소펜틸)아미노]-1-피롤리딘일]-1-시클로프로필-6-플루오르-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  18. 제11항에 있어서, 7-[3-[(2-아미노-4-카복시-1-옥소부틸)아미노]-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  19. 제11항에 있어서, 7-[3-[(2,6-디아미노-1-옥소헥실)아미노]-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  20. 제11항에 있어서, 7-[3-(아미노페닐아세틸)아미노]-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것이 광학 이성체인 화합물.
  21. 제11항에 있어서, 7-[3-[[2-아미노-1-옥소-3-페닐프로필)아미노]메틸]-3-메틸-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  22. 제11항에 있어서, 7-[3-[[(2-아미노-1-옥소프로필)아미노]메틸]-3-메틸-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  23. 제11항에 있어서, 7-[3-[[(아미노페닐아세틸)아미노]메틸]-3-메틸-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  24. 제11항에 있어서, 7-[3-[[(아미노페닐아세틸)아미노]메틸]-3-메틸-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  25. 제11항에 있어서, 7-[3-[[2-아미노-4-카복시-1-옥소부틸아미노]메틸-3-메틸-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  26. 제11항에 있어서, 7-[3-[[(2,6-디아미노-1-옥소헥실)아미노]메틸]-3-메틸-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  27. 제11항에있어서, 7-[3-[[(2,5-디아미노-1,5-디옥소펜틸)아미노]메틸-3-메틸-1-피롤리딘일]-1-시클로프로필-6-플루오로-1,4-디하이드로-4-옥소-1,8-나프티리딘-3-카복실산 또는 이것의 광학 이성체인 화합물.
  28. 제11항에 있어서, 7-[3-[[(2-아미노-1-옥소프로필)아미노]-1-피로리딘일]-1-시클로프로필-6,8-디플루오로-1,4-디하이드로-4-옥소-3-퀴놀린카복실산 또는 이것의 광학 이성체인 화합물.
  29. 제28항 화합물의[S-(R*,R*)] 이성체.
  30. 담체 또는 부형제와 함께 항균적으로 효과적인 양의 제1항 화합물로 이루어진 제약학적 조성물.
  31. 박테리아 감염으로 고통받는 숙주에서 제30항의 제약학적 조성물을 단위 투약 형태로 투여하는 것으로 이루어지는, 박테리아 감염을 치료하는 방법.
  32. - 아미노 그룹,R5로부터 산 가수분해 또는 촉매 수소화에 의해 보호그룹을 제거하고, 원한다면 결과의 유리산을 공지된 방법으로 제약학적으로 허용가능한 염기 염 또는 제약학적으로 허용가능한 산 부가염으로 전환시키는 것으로 이루어지는 제1항 화합물을 제조하는 방법.
  33. 제32항에 있어서, 보호그룹이- 부톡시카보닐이고 전술한 그룹이 산 가수분해로 제거되는 방법.
  34. 제33항에 있어서, 가수분해가 수성 염산내에서 실행되는 방법.
  35. 제32항에 있어서, 보호그룹이 벤질옥시카보닐이고 전술한 그룹이 촉매 수소화로 제거되는 방법.
  36. 제35항에 있어서, 탄소상의 팔라듐이 촉매로서 사용되는 방법.
  37. 다음 구조식의 화합물을
    식중,Z′는
    R′4는 -(CR2R3)n-NR2H
    Pro는 보호그룹을 나타내는 구조식화합물 또는 그것의 활성화된 산과 활성화된 산하에서 반응시키고, 산 가수분해나 촉매 수소화로 보호그룹을 제거하며, 원한다면 결과의 생성물을 공지된 방법으로 이것의 제약학적으로 허용가능한 염기 또는 산 부가염으로 전환시키는 것으로 이루어지는, 제1항 화합물을 제조하는 방법.
  38. 제36항에 있어서,Pro가 t-부톡시카보닐 또는 벤질옥시카보닐인 방법.
  39. L이 이탈 그룹인 다음 구조식의 화합물을
    R5내의- 아미노 그룹이 보호되는 구조식 ZH 아민과 반응시키고 산 가수분해나 촉매 수소화로 보호그룹을 제거시키며, 원한다면 결과의 화합물을 공지된 방법으로 이것이 제약학적으로 허용가능한 염기 또는 산 부가염으로 전환시키는 것으로 이루어지는, 제1항의 다음 구조식 화합물을 제조하는 방법.
    식중, Z는
  40. 제39항에 있어서, L이 불소 또는 염소인 방법.
  41. 제40항에 있어서, 보호그룹이 t- 부틸옥시카보닐 또는 벤질옥시카보닐인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019880010617A 1987-08-21 1988-08-20 7-치환체의 측쇄에 α-아미노산을 포함하는 퀴놀론 및 나프티리딘 항균제 KR0120389B1 (ko)

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Application Number Priority Date Filing Date Title
US8795087A 1987-08-21 1987-08-21
US087,950 1987-08-21
US220,177 1988-07-20
US07/220,177 US4851418A (en) 1987-08-21 1988-07-20 Naphthyridine antibacterial agents containing an α-amino acid in the side chain of the 7-substituent

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CA (1) CA1339216C (ko)
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DK (1) DK172152B1 (ko)
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NO (1) NO171979C (ko)
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Families Citing this family (56)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ATE75740T1 (de) * 1985-06-26 1992-05-15 Daiichi Seiyaku Co Pyridoncarbonsaeurederivate.
IN166416B (ko) * 1985-09-18 1990-05-05 Pfizer
JPH089597B2 (ja) * 1986-01-21 1996-01-31 杏林製薬株式会社 選択毒性に優れた８‐アルコキシキノロンカルボン酸およびその塩並びにその製造方法
ATE58538T1 (de) * 1986-07-04 1990-12-15 Chemie Linz Gmbh 4-chinolon-3-carbonsaeurederivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische praeparate.
US4780468A (en) * 1987-08-07 1988-10-25 Warner-Lambert Company 8-trifluoromethyl quinolones as antibacterial agents
MY105136A (en) * 1988-04-27 1994-08-30 Daiichi Seiyaku Co Optically active pyridonecarboxylic acid derivatives.
DE68920773T2 (de) * 1988-05-19 1995-05-18 Chugai Pharmaceutical Co Ltd Chinoloncarbonsäure-Derivate.
JP2844079B2 (ja) * 1988-05-23 1999-01-06 塩野義製薬株式会社 ピリドンカルボン酸系抗菌剤
FI95130C (fi) * 1988-07-20 1995-12-27 Sankyo Co Menetelmä lääkeaineena käyttökelpoisten 4-oksokinoliini-3-karboksyylihapon johdannaisten valmistamiseksi
US5057523A (en) * 1988-09-22 1991-10-15 Abbott Laboratories Dipeptide quinolone derivatives
US5057520A (en) * 1989-03-24 1991-10-15 Abbott Laboratories 7-(peptidylpyrolidinyl)naphthyridine antibacterial compounds
IE76284B1 (en) * 1988-09-22 1997-10-08 Abbott Lab Amino acid quinoline and naphthyridine derivatives
CA2001203C (en) * 1988-10-24 2001-02-13 Thomas P. Demuth, Jr. Novel antimicrobial dithiocarbamoyl quinolones
EP0997466A1 (en) * 1988-10-24 2000-05-03 PROCTER & GAMBLE PHARMACEUTICALS, INC. Novel antimicrobial lactam-quinolones
US5262417A (en) * 1988-12-06 1993-11-16 The Upjohn Company Antibacterial quinolone compounds
US4916141A (en) * 1989-03-28 1990-04-10 Warner-Lambert Company (S)-7-(3-amino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid
CA2012681A1 (en) * 1989-03-31 1990-09-30 Masayasu Okuhira Quinolone derivatives, preparation processes thereof, and antibacterial agents containing the same
DE3910920A1 (de) * 1989-04-05 1990-10-11 Bayer Ag Enantiomerenreine 7-(3-amino-1-pyrrolidinyl)-chinolon- und -naphthyridoncarbonsaeuren
US5164402A (en) * 1989-08-16 1992-11-17 Pfizer Inc Azabicyclo quinolone and naphthyridinone carboxylic acids
US5385913A (en) * 1989-10-06 1995-01-31 Pfizer Inc. 1,4-dihydro-4-oxo-3-quinoline derivatives as selectively toxic mammalian antibacterial agents
WO1991004972A1 (en) * 1989-10-06 1991-04-18 Pfizer Inc. 1,4-dihydro-4-oxo-3-quinoline derivatives as selectively toxic mammalian antibacterial agents
US5084276A (en) * 1990-01-05 1992-01-28 Abbott Laboratories Quinolone carboxylic acid compositions with polymeric additive to reduce vein irritation
AU640481B2 (en) 1990-04-18 1993-08-26 Norwich Eaton Pharmaceuticals, Inc. Penicillan or cephalosporin derivatives of quinolonyl
AU6367690A (en) * 1990-07-10 1992-05-21 Hokuriku Pharmaceutical Co. Ltd. Optically active thiazetoquinoline-3-carboxylic acid compound, method for preparation thereof, and a pharmaceutical composition comprising the same
US5342846A (en) * 1990-12-05 1994-08-30 Synphar Laboratories, Inc. 7-substituted-6-fluoro-1,4-dihydro-4-oxo-quinoline-3-carboxylic acid compounds and 7-(substituted triazolyl pyrrolidin-1-yl) 4-oxoquinoline-3-carboxylic acid derivatives useful as antibacterial agents
CA2058640A1 (en) * 1991-01-25 1992-07-26 Richard R. Scherschlicht Tricyclic pyridone derivative
ZA92803B (en) 1991-02-06 1992-11-25 Igen Inc Method and apparatus for magnetic microparticulate based luminescene asay including plurality of magnets
FR2673426B1 (fr) * 1991-03-01 1993-07-16 Bouchara Sa Nouvelles quinolones, leur procede de preparation et les compositions en refermant.
FR2676445B1 (fr) * 1991-05-16 1995-02-03 Esteve Labor Dr Derives de pyridone amino acide azetidinyl substitues, leur preparation et leur application en tant que medicaments.
WO1992021659A1 (en) * 1991-05-28 1992-12-10 Daiichi Pharmaceutical Co., Ltd. Pyridonecarboxylic acid derivative
US5177217A (en) * 1992-04-27 1993-01-05 Warner-Lambert Company Process for the manufacture of (S)-3-amino-1-substituted-pyrrolidines
FR2692577B1 (fr) * 1992-05-26 1996-02-02 Bouchara Sa Nouvelles quinolones fluorees, leur procede de preparation et les compositions pharmaceutiques en renfermant.
US5290794A (en) * 1992-10-27 1994-03-01 Warner Lambert Co. Soluble calcium lactate antibacterial complexes as non-irritating parenteral forms
AU4272793A (en) * 1993-04-24 1994-11-21 Korea Research Institute Of Chemical Technology Novel quinolone carboxylic acid derivatives and process for preparing the same
KR950018003A (ko) * 1993-12-09 1995-07-22 스미스클라인 비참 피엘씨 신규한 퀴놀론 유도체 및 그의 제조 방법
EP0773214A4 (en) * 1994-07-18 1998-04-15 Ube Industries TRIFLUORMETHYLQUINOLINE CARBONIC ACID DERIVATIVES
US5602254A (en) * 1995-05-26 1997-02-11 Warner-Lambert Company Method for making quinoline carboxylic acids or naphthyridine carboxylic acids in free base form
US5939550A (en) * 1995-06-15 1999-08-17 Pfizer Inc. Process for preparing derivatives of azabicyclo naphthyridine carboxylic acid comprising a dipeptide
JP4057088B2 (ja) * 1996-04-22 2008-03-05 株式会社カネカ ピロリジン誘導体の製造方法
ATE247089T1 (de) * 1996-11-28 2003-08-15 Wakunaga Pharma Co Ltd Pyridoncarbonsäurederivate oder ihre salze und diese als aktive bestandteile enthaltende medikamente
US6608078B2 (en) 2000-05-08 2003-08-19 Wockhardt Limited Antibacterial chiral 8-(substituted piperidino)-benzo [i,j] quinolizines, processes, compositions and methods of treatment
US7098219B2 (en) 2000-08-01 2006-08-29 Wockhart Limited Inhibitors of cellular efflux pumps of microbes
SE0003795D0 (sv) 2000-10-20 2000-10-20 Astrazeneca Ab Pharmaceutically useful compounds
US6964966B2 (en) 2001-04-25 2005-11-15 Wockhardt Limited Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
US6878713B2 (en) 2001-04-25 2005-04-12 Wockhardt Limited Generation triple-targeting, chiral, broad-spectrum antimicrobial 7-substituted piperidino-quinolone carboxylic acid derivatives, their preparation, compositions and use as medicaments
WO2003099815A1 (en) 2002-05-28 2003-12-04 Wockhardt Limited Crystalline fluoroquinolone arginine salt form
CA2537066C (en) 2003-09-04 2011-05-24 Wockhardt Limited Benzoquinolizine-2-carboxylic acid arginine salt tetrahydrate
EP1676837A4 (en) * 2003-10-08 2008-09-10 Teijin Pharma Ltd METHOD FOR PRODUCING AN AMINOPYRROLIDINE DERIVATIVE AND AN INTERMEDIATE COMPOUND
KR100939347B1 (ko) 2005-07-20 2010-01-29 (주)카이로드 광학적으로 순수한 (ｓ)-3-히드록시 피롤리딘의 제조방법
CN101239937B (zh) * 2007-02-07 2010-05-19 上海雅本化学有限公司 一种光学活性r-(-)-1-苄氧羰基-3-氨基吡咯烷及其盐酸盐的制备方法
CA2693473A1 (en) * 2007-07-17 2009-01-22 Amgen Inc. Thiadiazole modulators of pkb
US7902227B2 (en) * 2007-07-27 2011-03-08 Janssen Pharmaceutica Nv. C-7 isoxazolinyl quinolone / naphthyridine derivatives useful as antibacterial agents
WO2009122997A1 (ja) * 2008-04-02 2009-10-08 株式会社カネカ （ｓ）－３－（１－シアノ－１，１－ジフェニルメチル）－ピロリジンの製造法
EP2361244B1 (en) 2008-11-24 2013-07-10 Council of Scientific & Industrial Research A process for the preparation of optically active n-benzyl-3 hydroxypyrrolidines
CN114989165A (zh) * 2022-05-30 2022-09-02 青岛大学附属医院 一种抗持留菌和生物膜菌的化合物或组合物及其用途
EP4382529A1 (en) 2022-12-07 2024-06-12 Bayer Consumer Care AG A process for preparing pure (3s)-pyrrolidin-3-ol and pure (3s)-pyrrolidin-3-ol hydrochloride

Family Cites Families (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5630964A (en) * 1979-08-22 1981-03-28 Kyorin Pharmaceut Co Ltd Novel substituted quinolinecarboxylic acid and its preparation
JPS58174367A (ja) * 1982-04-07 1983-10-13 Tanabe Seiyaku Co Ltd キノリン誘導体及びその製法
US4665079A (en) * 1984-02-17 1987-05-12 Warner-Lambert Company Antibacterial agents
IE55898B1 (en) * 1982-09-09 1991-02-14 Warner Lambert Co Antibacterial agents
DE3306771A1 (de) * 1983-02-25 1984-08-30 Bayer Ag, 5090 Leverkusen Chinoloncarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
DE3318145A1 (de) * 1983-05-18 1984-11-22 Bayer Ag, 5090 Leverkusen 7-amino-1-cyclopropyl-6,8-difluor-1,4-dihydro-4-oxo-3-chinolincarbonsaeuren, verfahren zu ihrer herstellung sowie diese enthaltende antibakterielle mittel
JPS60126271A (ja) * 1983-12-09 1985-07-05 Kyorin Pharmaceut Co Ltd キノロンカルボン酸誘導体
ZA85853B (en) * 1984-02-17 1986-09-24 Warner Lambert Co Antibacterial agents
JPS60178867A (ja) * 1984-02-24 1985-09-12 Dai Ichi Seiyaku Co Ltd ジハロゲノキノリン誘導体
US4571396A (en) * 1984-04-16 1986-02-18 Warner-Lambert Company Antibacterial agents
JPS60250573A (ja) * 1984-05-25 1985-12-11 富士通株式会社 電気接続用ソケツト
JPS61205258A (ja) * 1985-03-08 1986-09-11 Kyorin Pharmaceut Co Ltd キノロンカルボン酸誘導体及びその製造方法
US4657913A (en) * 1985-04-18 1987-04-14 Warner-Lambert Company Trifluoro- quinoline -3- carboxylic acids and their use as anti-bacterial agents
JPS62469A (ja) * 1985-06-27 1987-01-06 Dainippon Pharmaceut Co Ltd 新規キノロン誘導体、そのエステルおよびその塩
US4668680A (en) * 1985-12-12 1987-05-26 Warner-Lambert Company 5-amino-6,8-difluoroquinolones as antibacterial agents

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FI883807A0 (fi) 1988-08-17
NZ225870A (en) 1990-12-21
US4851418A (en) 1989-07-25
AU2062988A (en) 1989-02-23
KR0120389B1 (ko) 1997-11-04
DK172152B1 (da) 1997-12-01
NO171979B (no) 1993-02-15
FI90237B (fi) 1993-09-30
DK467388D0 (da) 1988-08-19
PH25460A (en) 1991-07-01
IE882363L (en) 1989-02-21
FI90237C (fi) 1994-01-10
JPH01125371A (ja) 1989-05-17
EP0304087B1 (en) 1994-03-30
HK1000802A1 (en) 1998-05-01
DE3888754D1 (de) 1994-05-05
AU608881B2 (en) 1991-04-18
CA1339216C (en) 1997-08-05
EP0304087A3 (en) 1989-10-25
NO883722L (no) 1989-02-22
EP0304087A2 (en) 1989-02-22
DE3888754T2 (de) 1994-07-14
NO883722D0 (no) 1988-08-19
PT88289B (pt) 1995-03-31
JP2679818B2 (ja) 1997-11-19
ES2063011T3 (es) 1995-01-01
DK467388A (da) 1989-02-22
NO171979C (no) 1993-05-26
FI883807A (fi) 1989-02-22
IE62787B1 (en) 1995-02-22
PT88289A (pt) 1989-09-14

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