KR950702537A - 키랄[[(2-브로모에틸)아미노]메틸]-2-니트로-1H-이미디졸-1-에탄올 및 관련화합물의 신규 제조 방법(Novel Process for preparing Chiral [[(2-Bromoethyl)aminomethyl]-2-nitro-1H-imidazol-1-ethanol and Related Compounds) - Google Patents

키랄[[(2-브로모에틸)아미노]메틸]-2-니트로-1H-이미디졸-1-에탄올 및 관련화합물의 신규 제조 방법(Novel Process for preparing Chiral [[(2-Bromoethyl)aminomethyl]-2-nitro-1H-imidazol-1-ethanol and Related Compounds) Download PDF

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KR950702537A
KR950702537A KR1019950700361A KR19950700361A KR950702537A KR 950702537 A KR950702537 A KR 950702537A KR 1019950700361 A KR1019950700361 A KR 1019950700361A KR 19950700361 A KR19950700361 A KR 19950700361A KR 950702537 A KR950702537 A KR 950702537A
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nitro
compound
chiral
carbon atoms
amino
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KR1019950700361A
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제럴드 아담스 아담스
에드워드 마틴 필덴
매튜 알렉산더 네일러
이안 제임스 스트래트포드
블라디미르 제누크 베일린
안토니 덴버 서셀
하워드 다니엘 홀리스 쇼왈터
Original Assignee
로즈 암스트롱
워너 램버트 캄파니
쥐.에프.스티븐슨
브리티쉬 테크놀로지 그룹 리미티드
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Publication of KR950702537A publication Critical patent/KR950702537A/ko

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    • 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
    • C07D403/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • 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
    • C07D233/66—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 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
    • C07D233/91—Nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

본 발명은 하기 식
(식 중, X는 할로겐 또는임)
의 방사선 증감제 또는 화학 증감제로서 유용한 키랄 화합물, 이 화합물을 제조하는데 사용한 중간체 및 기재된 화합물을 제조하는 신규 방법에 관한 것이다.

Description

키랄[[2-브로모에틸)아미노]메틸]-2-니트로-1H-이미디졸-1-에탄올 및 관련화합물의 신규 제조 방법(Novel Porcess for preparing Chiral [[(2-Bromoethyl)aminomethyl]-2-nitro-1H-imidazol-1-ethanol and Related Compounds)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (13)

  1. 기의 배열에 따라 (R)- 또는 (S)- 형태를 취하는 하기 일반식의 키랄화합물.
    상기 식 중, X는 할로겐 또는이고, R1은 OH, 메틸, 페닐, 또는 탄소 원자수 1 내지 4의 저급 알킬, 탄소 원자수 1 내지 4의 저급 알콕시, 히드록시, 할로겐 니트로, 아미노 또는 트리플루오로메틸로 치환된 페닐이다.
  2. 제1항에 있어서, (R)-거울상 이성질체인 것인 화합물.
  3. 제1항에 있어서, X가 염소 또는 브롬인 것인 화합물.
  4. 제3항에 있어서, X가 브롬인 것인 화합물.
  5. 제4항에 있어서, (R)-(+)-α-[[(2-브로모에틸)아미노]메틸]-2-니트로-1H-이미다졸-1-에탄올 일브롬화수소산염인 것인 화합물.
  6. 기의 배열에 따라 (R)- 또는 (S)- 형태를 취하는 하기 일반식의 키랄 화합물.
    상기 식 중, R은 탄소 원자수 1 내지 4의 저급 알킬기, 페닐, 또는 탄소 원자수 1 내지 4의 저급 알킬, 탄소 원자수 1 내지 4의 저급 알콕시, 히드록시, 할로겐, 니트로, 아미노 또는 트리플루오로메틸로 치환된 페닐이다.
  7. 제6항에 있어서, R이 메틸인 것인 (S)-(+) 거울상 이성질체 화합물.
  8. 기의 배열에 따라 (R)- 또는 (S)- 형태를 취하는 하기 일반식의 키랄화합물.
  9. 제8항에 있어서, (R)-(-) 거울상 이성질체인 것인 화합물.
  10. 기의 배열에 따라 (R)- 또는 (S)- 형태를 취하는 하기 일반식의 키랄화합물.
  11. 제10항에 있어서, (S)-(-) 거울상 이성질체인 것인 화합물.
  12. 키랄 2-니트로-1-(2-옥시라닐메틸)-1H-이미다졸을 적합한 촉매의 존재하에 하기 식
    (식 중, R은 탄소 원자수 1 내지 4의 저급 알킬기, 페닐 또는 탄소 원자수 1 내지 4의 저급 알킬기, 탄소 원자수 1 내지 4의 저급 알콕시, 히드록시, 할로겐, 니트로, 아미노, 또는 트리플루오로메틸로 치환된 페닐임)의 2-옥사졸리디논과 반응시켜 하기 식
    (식 중, R은 정의된 의미를 가짐)의 키랄 화합물을 얻고, 이것을 (a) 가수 분해시켜 키랄 3-[2-히드록시-3-(2-니트로-1H-이미다졸-1-일)프로필]-2-옥사졸리디논을 얻고, 이것을 HX(여기서, X는 상기 정의된 바와 같음)의 산으로 처리하거나, 또는 (b) 상기한 바와 같은 산을 사용하여 일단계 반응으로 처리하는 것을 포함하는, 기의 배열에 따라 (R)- 또는 (S)- 형태를 취하는 하기 일반식의 키랄화합물 또는 이들의 제약상 허용되는 염의 제조방법.
    상기 식 중, X는 할로겐 또는이고, R1은 OH, 메틸, 페닐, 또는 탄소 원자수 1 내지 4의 저급 알킬, 탄소 원자수 1 내지 4의 저급 알콕시, 히드록시, 할로겐 니트로, 아미노 또는 트리플루오로메틸로 치환된 페닐이다.
  13. (S)-2-니트로-1-(2-옥시라닐메틸)-1H-이미다졸을 칼륨 트리메틸실라놀레이트의 존재하에 하기 식
    의 2-옥사졸리디논과 반응시켜 하기 식
    의 화합물의 (S)-거울상 이성질체를 얻고, 이것을 아세트산의 존재하에 브롬화수소산화 반응시키는 것을 포함하는, (R)-(+)-α-[[(2-브로모에틸)아미노]메틸]-2-니트로-1H-이미다졸-1-에탄올 일브롬화 수소산염의 제조 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019950700361A 1992-07-31 1993-07-26 키랄[[(2-브로모에틸)아미노]메틸]-2-니트로-1H-이미디졸-1-에탄올 및 관련화합물의 신규 제조 방법(Novel Process for preparing Chiral [[(2-Bromoethyl)aminomethyl]-2-nitro-1H-imidazol-1-ethanol and Related Compounds) KR950702537A (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US92320992A 1992-07-31 1992-07-31
US923,209 1992-07-31
PCT/US1993/006973 WO1994015922A1 (en) 1992-07-31 1993-07-26 Novel process for preparing chiral [[(2-bromoethyl)amino]methyl]-2-nitro-1h-imidazol-1-ethanol and related compounds

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KR950702537A true KR950702537A (ko) 1995-07-29

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US (4) US5342959A (ko)
EP (1) EP0652870A1 (ko)
JP (1) JPH07509489A (ko)
KR (1) KR950702537A (ko)
AU (1) AU4784293A (ko)
CA (1) CA2136328A1 (ko)
CZ (1) CZ10395A3 (ko)
FI (1) FI950383A (ko)
HU (1) HUT71347A (ko)
MX (1) MX9304399A (ko)
SK (1) SK8495A3 (ko)
WO (1) WO1994015922A1 (ko)

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CN1314396C (zh) * 2005-04-28 2007-05-09 南京圣和药业有限公司 左旋奥硝唑在制备抗厌氧菌感染药物的应用
CN1332662C (zh) * 2005-04-29 2007-08-22 南京圣和药业有限公司 左旋奥硝唑的静脉给药制剂及其制备方法
CN1305469C (zh) * 2005-07-08 2007-03-21 南京圣和药业有限公司 左旋奥硝唑在制备抗寄生虫感染的药物中的应用
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HUT71347A (en) 1995-11-28
US5342959A (en) 1994-08-30
FI950383A0 (fi) 1995-01-27
AU4784293A (en) 1994-08-15
US5543527A (en) 1996-08-06
FI950383A (fi) 1995-01-27
CZ10395A3 (en) 1995-11-15
CA2136328A1 (en) 1994-07-21
HU9500269D0 (en) 1995-03-28
MX9304399A (es) 1994-02-28
SK8495A3 (en) 1995-08-09
US5481000A (en) 1996-01-02
EP0652870A1 (en) 1995-05-17
US5659048A (en) 1997-08-19
WO1994015922A1 (en) 1994-07-21
JPH07509489A (ja) 1995-10-19

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