KR870001193A - β-락탐 항생물질의 제조방법 - Google Patents

β-락탐 항생물질의 제조방법 Download PDF

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KR870001193A
KR870001193A KR1019860005753A KR860005753A KR870001193A KR 870001193 A KR870001193 A KR 870001193A KR 1019860005753 A KR1019860005753 A KR 1019860005753A KR 860005753 A KR860005753 A KR 860005753A KR 870001193 A KR870001193 A KR 870001193A
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compound
general formula
formula
alkyl
phenyl
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KR1019860005753A
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KR900005257B1 (ko
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알버트 에반즈 데이비드
브리안 죠그렌 에릭
Original Assignee
프레지던트 앤드 펠로우즈 오브 하버드 칼리지
로버트 쉔톤
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Publication of KR870001193A publication Critical patent/KR870001193A/ko
Priority to KR1019900008404A priority Critical patent/KR900005322B1/ko
Application granted granted Critical
Publication of KR900005257B1 publication Critical patent/KR900005257B1/ko

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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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
    • C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
    • C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings 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
    • C07D263/18—Oxygen atoms
    • C07D263/20—Oxygen atoms attached in position 2
    • C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
    • 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
    • C07D413/04—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 directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
    • C07D463/16—Nitrogen atoms
    • C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
    • C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Cephalosporin Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Catalysts (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

내용 없음.

Description

β-락탐 항생물질의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (4)

  1. A) 하기 일반식(10b) 화합물을 로듐(II) 촉매하에서 폐환시키거나 ; B) 하기 일반식(b) 화합물을 장해된 염기와 반응시킴을 특징으로 하여, 하기 일반식(X)의 시스-에난티오머 또는 이의 산부가염을 제조하는 방법.
    상기식에서, R6은 수소 : 통상적인 아미노보호그룹 : 또는 일반식 R1CO그룹[여기서, R1은 C1-C6알킬, 일반식의 페닐그룹(여기서, a 및 a′는 독립적으로 수소, C1-C4알킬, C1-C4알콕시 또는 할로겐이다), 일반식그룹(여기서, Z는 산소 또는 황이고, m은 0 또는 1이며, a 및 a′는 상기 정의한 바와 같다), 또는 R1 00(여기서, R1 0은 C1-C4알킬, C5-C7사이클로알킬, 벤질, 니트로벤질, 메톡시벤질 또는 할로벤질이다)이다]이고, 단, 일반식(10b) 및 (b)에서 R6은 수소가 아니며 : R2는 통상적인 카복시보호그룹이며 ; R7은 C1-C6알킬, 벤질, 또는 C1-C4알킬, C1-C4알콕시 또는 할로로 임의 치환된 페닐이다.
  2. 제1항에 있어서, R6이 R1CO인 화합물로부터 방법(A)에 따라 일반식(X) 화합물을 제조하는 방법.
  3. 제1항에 있어서, 장해된 염기로서 리튬헥사메틸디실라잔을 사용하여 R7이 -S-ph인 화합물로부터 방법(B)에 따라 일반식(X) 화합물을 제조하는 방법.
  4. 하기 일반식(5a) 화합물을 하기 일반식(6a) 화합물과 반응시켜 Y가 -CH=CH-인 일반식(I) 화합물을 생성시킨 다음, 생성된 화합물을 임의로 수소화시켜 Y가 -CH2-CH2-인 일반식(I) 화합물을 생성시킴을 특징으로 하여 일반식(I) 화합물을 제조하는 방법.
    상기식에서, Ar은 페닐, C1-C4알킬페닐, 할로페닐, C1-C4알콕시페닐, 나프틸, 티에닐, 푸릴, 벤조티에닐 또는 벤조푸릴이고 : R은 페닐, C1-C4알킬페닐, C1-C4알콕시페닐 또는 할로페닐이며 : Y는 -CH=CH- 또는 -CH2-CH2-이고 : R′는 페닐, C1-C4알킬페닐, C1-C4알콕시페닐, 할로페닐, 푸릴 또는 나프틸이며 : X′는 클로로, 브로모, 트리플루오로아세톡시 또는 -OP(=O)X2(여기서, X는 할로겐이다)이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019860005753A 1985-05-17 1986-07-16 β-락탐 항생물질 및 그의 제조방법 KR900005257B1 (ko)

Priority Applications (1)

Application Number Priority Date Filing Date Title
KR1019900008404A KR900005322B1 (ko) 1985-05-17 1990-06-08 β-락탐 항생물질 제조용 중간체

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US06/755,982 US4665171A (en) 1985-07-17 1985-07-17 Process and intermediates for β-lactam antibiotics
US755982 1985-07-17

Related Child Applications (1)

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KR1019900008404A Division KR900005322B1 (ko) 1985-05-17 1990-06-08 β-락탐 항생물질 제조용 중간체

Publications (2)

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KR870001193A true KR870001193A (ko) 1987-03-12
KR900005257B1 KR900005257B1 (ko) 1990-07-21

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Country Status (22)

Country Link
US (1) US4665171A (ko)
EP (2) EP0209352B1 (ko)
JP (2) JPH0762015B2 (ko)
KR (1) KR900005257B1 (ko)
CN (1) CN1015178B (ko)
AR (1) AR243186A1 (ko)
AT (2) ATE63118T1 (ko)
AU (2) AU595216B2 (ko)
CA (1) CA1310323C (ko)
DE (2) DE3650474T2 (ko)
DK (2) DK173456B1 (ko)
ES (2) ES2000516A6 (ko)
GR (1) GR861857B (ko)
HK (1) HK1007140A1 (ko)
HU (2) HU906465D0 (ko)
IE (1) IE58997B1 (ko)
IL (1) IL79420A (ko)
NZ (1) NZ216871A (ko)
PT (1) PT82989B (ko)
RU (1) RU1794079C (ko)
SU (1) SU1579460A3 (ko)
ZA (1) ZA865274B (ko)

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JP2002535680A (ja) 1999-01-27 2002-10-22 ファルマシア・アンド・アップジョン・カンパニー 延長因子ｐ活性モジュレーターのアッセイ方法
JP4916929B2 (ja) * 2007-03-23 2012-04-18 ヤマハ発動機株式会社 直交型ロボット
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Publication number Publication date
IE58997B1 (en) 1993-12-15
DE3679002D1 (de) 1991-06-06
CA1310323C (en) 1992-11-17
EP0209352A2 (en) 1987-01-21
JPS6242985A (ja) 1987-02-24
EP0362902A3 (en) 1990-08-01
SU1579460A3 (ru) 1990-07-15
DK335686D0 (da) 1986-07-15
ES2000516A6 (es) 1988-03-01
AU6016686A (en) 1987-01-22
JPH0762015B2 (ja) 1995-07-05
IE861900L (en) 1987-01-17
AU4793490A (en) 1990-05-10
EP0362902B1 (en) 1996-01-17
JPH07300476A (ja) 1995-11-14
ATE63118T1 (de) 1991-05-15
KR900005257B1 (ko) 1990-07-21
CN1015178B (zh) 1991-12-25
AR243186A1 (es) 1993-07-30
GR861857B (en) 1986-11-18
PT82989B (pt) 1989-01-30
HU201931B (en) 1991-01-28
DK16096A (da) 1996-02-15
EP0209352A3 (en) 1988-04-20
HK1007140A1 (en) 1999-04-01
CN86104783A (zh) 1987-02-04
PT82989A (en) 1986-08-01
DK173456B1 (da) 2000-11-27
EP0362902A2 (en) 1990-04-11
ES2005752A6 (es) 1989-03-16
DE3650474T2 (de) 1996-06-13
JP2634775B2 (ja) 1997-07-30
DK335686A (da) 1987-02-25
DE3650474D1 (de) 1996-02-29
ZA865274B (en) 1988-02-24
AU619938B2 (en) 1992-02-06
EP0209352B1 (en) 1991-05-02
HU906465D0 (en) 1991-04-29
US4665171A (en) 1987-05-12
ATE133172T1 (de) 1996-02-15
AU595216B2 (en) 1990-03-29
RU1794079C (ru) 1993-02-07
HUT41786A (en) 1987-05-28
NZ216871A (en) 1989-10-27
IL79420A (en) 1992-01-15

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