KR920018007A - 퀴놀론 항생물질의 제조에 유용한 베타- 케토에스테르의 제조방법 - Google Patents

퀴놀론 항생물질의 제조에 유용한 베타- 케토에스테르의 제조방법 Download PDF

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KR920018007A
KR920018007A KR1019910004705A KR910004705A KR920018007A KR 920018007 A KR920018007 A KR 920018007A KR 1019910004705 A KR1019910004705 A KR 1019910004705A KR 910004705 A KR910004705 A KR 910004705A KR 920018007 A KR920018007 A KR 920018007A
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general formula
imidazolyl
compound
chloro
formula
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KR1019910004705A
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KR930005059B1 (ko
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티. 오닐 브라이안
알. 부쉬 프랑크
에스. 레너 리챠드
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알렌 제이. 스피겔
화이자 인코포레이티드
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Priority to KR1019930008316A priority Critical patent/KR930006078B1/ko
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/67—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of saturated acids
    • C07C69/716—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
    • C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
    • C07C69/738—Esters of keto-carboxylic acids or aldehydo-carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Saccharide Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

Abstract

내용 없음

Description

퀴놀린 항생물질의 제조에 유용한 베타-케토에스테르의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식(Ⅲ)의 화합물을 하기 일반식(A)의 화합물과 반응 시킴을 포함하는, 하기 일반식(Ⅰ)화합물의 제조 방법:
    상기식들에서, Q는 〉C-H 또는 N이고, R1은 C1내지 C4알킬, 벤질 또는 p-니트로벤질이며, X 및 Y는 플로오로 및 클로로중에서 독립적으로 선택되고, Z는 플루오로, 클로로, 브로모, 1-이미다졸릴 또는 치환된 1-이미다졸릴이며, 여기서, 1-이미다졸릴 그룹은 C1내지 C4알킬로부터 독립적으로 선택되는 1또는 2개의 치환체로 치환되고, M은 알킬리 토금속, Cu 또는 Mn이고, n은 2이며, Vp-(여기서, p는 1또는 2이다)는 하기 일반식(Va)의 음이온 또는 하기 일반식(Vb)의 디음이온이나, 단, Z가 1-이미다졸릴 또는 치환된 1-이미다졸릴인 경우에는, M은 마그네슘, 구리 또는 망간이며, Z가 플루오로, 클로로 또는 브로모인 경우에는, Vp-는 일반식(Vb)의 다음이온이다:
    (여기서, R1은 C1내지 C6알킬 또는 파라니트로 벤질이다).
  2. 제1항에 있어서, Mn+가 Mg++이고 Vp-가 하기 일반식(Vb)의 다음이온인 방법:
    상기식에서, R1은 제1항에서 정의한 바와 같다.
  3. 제1항에 있어서, Vp-가 제1항에서 언급한 바와 같은 일반식(Vb) (여기서, R1은 제1항에서 정의한 바와 같다)의 다음이온이고, 상기 다음이온이 제1항에서 언급한 바와 같은 일반식(Vb) (여기서, R1은 제1항에서 정의한 바와 같다)의 음이온을 일반식 R2MgW(여기서, R2는 C1내지 C4알킬 또는 페닐이고 W는 클로로, 브로모 또는 요오도이다)의 그리나드 시약과 반응 시킴으로써 수득되는 방법.
  4. 제1항 또는 제3항에 있어서, 다음이온을 동일 반응계내에서 제조하는 방법.
  5. 제1항에 있어서, Z가 플루오로, 클로로 또는 브로모이고, Vp-가 제1항에서 언급한 바와 같은 일반식(Vb) (여기서, R1은 제1항에서 정의한 바와 같다)의 다음이온이고, 상기 다음이온이 제1항에서 언급한 바와 같은 일반식(Vb) (여기서, R1은 제1항에서 정의한 바와 같다)의 음이온을 일반식 R2MgW(여기서, R2는 C1내지 C4알킬 또는 페닐이고 W는 클로로, 브로모 또는 요오도이다)의 그리나드 시약과 반응 시킴으로써 수득되는 방법.
  6. 제5항에 있어서, W가 브로모 또는 클로로인 방법.
  7. 제1항에 있어서, Z가 1-이미다졸릴 또는 치환된 1-이미다졸릴이고, Mn+가 Mg++이며, 일반식〔Mn+ p〕〔Vp- n〕의 화합물이 일반식 〔M|n+ p〕〔Vp- n〕(여기서, Mn+는 Mg++이외의 다른 것이다)의 화합물을, 마그네슘 염과 함께, 제1항에 언급한 바와 같은 일반식(Ⅲ)(여기서, X 및 Y는 제1항에서 정의한 바와 같고 Z는 1-이미다졸릴 또는 치환된 1-이미다졸릴이다)의 화합물과 반응시킴으로써 동일 반응계내에서 수득되는 방법.
  8. 제1항에 있어서, 일반식 〔Mn+ p〕〔Vp- n〕의 상기 화합물이 일반식
    제1항에서 정의한 바와 같다)의 화합물인 방법.
  9. 하기 일반식(Ⅲ)의 화합물:
    상기식에서, Q는 〉CH이고, Z는 1-이미다졸릴 또는 치환된 1-이미다졸릴이며, 여기에서, 1-이미다졸릴 그룹은 C1내지 C4알킬로부터 독립적으로 선택되는 1또는 2개의 치환체로 치환되고, X는 플루오로 또는 클로로이며, Y는 플루오로 또는 클로로이다.
  10. 하기 일반식의 화합물:
    상기식에서, Z는 1-이미다졸릴이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019910004705A 1990-03-27 1991-03-25 퀴놀론 항생물질의 제조에 유용한 베타-케토에스테르의 제조방법 KR930005059B1 (ko)

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KR1019930008316A KR930006078B1 (ko) 1990-03-27 1993-05-14 베타-케토에스테르의 중간체

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US50015590A 1990-03-27 1990-03-27
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US (1) US5380860A (ko)
EP (1) EP0449445A3 (ko)
JP (1) JPH0648990A (ko)
KR (1) KR930005059B1 (ko)
CN (1) CN1041083C (ko)
AU (1) AU617066B1 (ko)
BR (1) BR9101188A (ko)
CA (1) CA2039306C (ko)
EG (1) EG19607A (ko)
FI (1) FI911465A (ko)
HU (1) HUT56826A (ko)
IE (1) IE910991A1 (ko)
IL (1) IL97617A (ko)
MY (1) MY108069A (ko)
NO (1) NO911229L (ko)
NZ (1) NZ237555A (ko)
PH (1) PH30994A (ko)
PL (1) PL289582A1 (ko)
PT (1) PT97130B (ko)
RU (1) RU2058977C1 (ko)
YU (1) YU53991A (ko)
ZA (1) ZA912263B (ko)

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EP0449445A3 (en) 1993-08-25
BR9101188A (pt) 1991-11-05
YU53991A (sh) 1993-11-16
PL289582A1 (en) 1992-06-01
KR930005059B1 (ko) 1993-06-15
ZA912263B (en) 1992-11-25
NO911229D0 (no) 1991-03-26
IL97617A0 (en) 1992-06-21
NO911229L (no) 1991-09-30
MY108069A (en) 1996-08-15
JPH0648990A (ja) 1994-02-22
IE910991A1 (en) 1991-10-09
CN1041083C (zh) 1998-12-09
EG19607A (en) 1995-07-27
CN1055177A (zh) 1991-10-09
EP0449445A2 (en) 1991-10-02
US5380860A (en) 1995-01-10
CA2039306A1 (en) 1991-09-28
PT97130A (pt) 1991-11-29
FI911465A (fi) 1991-09-28
FI911465A0 (fi) 1991-03-26
CA2039306C (en) 1999-01-26
AU617066B1 (en) 1991-11-14
HUT56826A (en) 1991-10-28
PT97130B (pt) 1999-02-26
IL97617A (en) 1998-08-16
PH30994A (en) 1997-12-23
RU2058977C1 (ru) 1996-04-27
NZ237555A (en) 1993-08-26

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