KR830009107A - 2-페넴 화합물의 제조방법 - Google Patents

2-페넴 화합물의 제조방법 Download PDF

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KR830009107A
KR830009107A KR1019820000375A KR820000375A KR830009107A KR 830009107 A KR830009107 A KR 830009107A KR 1019820000375 A KR1019820000375 A KR 1019820000375A KR 820000375 A KR820000375 A KR 820000375A KR 830009107 A KR830009107 A KR 830009107A
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아폰소 아드리아노
혼 프랭크
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스테이나 칸스타드, 로즈마리 아이젠링
쉐링 코포레이숀
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Abstract

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Description

2-페넴 화합물의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (18)

  1. 일반식(II)의 화합물을 3가 유기 포스포러스화합물과 반응시키고 이때 사용된 일반식(II)화합물이 이성체 혼합물인 경우에는 경우에 따라 생성화합물을 입체 이성체로 단리 및 분리시키기전 또는 뒤에 a) 하나이상의 보호그룹의 제거, b) 특정 관능기를 유기산으로 전환, c) 특정관능기를 약제학적으로 허용되는 염으로 전환, 및 d) 특정 관능기를 대사성 에스테를 그룹으로 전환시키는 조작중의 하나이상을 거침을 특징으로 하여 일반식(I)의 화합물 및 그의 약제학적으로 허용되는 염을 제조하는 방법.
    상기 식에서, R1은, 수소, 저급알킬, 아실아미노,(여기서 R4는 수소, 저급알킬, 아릴 또는 헤테로아릴이고, R5는 수소 또는 하이드록시보호그룹이고, R8는 할로겐이다), R9가 저급알킬 수소 또는 -S 보호그룹인 -SR9, 또는그룹을 나타내는데, R10및 R11중 하나는 -N 보호그룹이며 나머지는 수소, 저급알킬, 아릴, 아르알킬 및 아실가운데서 선택되거나 R10및 R11은 각각 수소, 저급알킬, 아르알킬, 아릴 및 아실중에서 선택되는데 단, 하나가 수소인 경우, 나머지는 아실이어야하며; R2는 저급알킬, 아릴, 아르알킬, 아미노알킬, N-보호아미노알킬, 하이드록시알킬, 0-보호하이드록시알킬, 티오알킬, 티오아릴, 티오헤테로아릴, 임의 에스테르화 α-아미노산잔기, 임의 에스테르화 α-(N보호된)아미노산잔기 또는 임의 에스테르화 알킬카복실그룹이며; R3는 니트릴, 테트라졸릴 또는 R6가 수소인 -COOR6, Hal이 할로겐을 나타내며 AIk는 알킬렌 라디칼을 나타내는 라디칼 C(Hal)3-Alk, 저급알킬 아릴, 아릴성그룹, 대사가능한 에스테르그룹 또는 카복시보호그룹이며; X 및 Z는 각각 황, 산소, 라디칼=NR7, (R7이 수소, 아실, 저급알킬, 아릴 또는 N-보호그룹), 또는 n이 1 또는 2인 -(CH2)n-이며, 일반식(II)에서는 R1, R2, R3, X 및 Z가 상기 정의된 바와 같으나 단, R5는 하이드록시 보호그룹이고, R9은 저급알킬 또는 S-보호그룹이며, R7은 수소가 아니고, 치환체 R2중의 카복시 그룹중의 어느것은 에스테르화되어 있으며 R6는 수소가 아니다.
  2. 제1항에 있어서, 3가 유기 포스포러스 화합물이 사이클릭 및/또는 아사이클릭 트리알킬포스파이트, 트리아릴 포스파이트, 혼합알킬아릴 포스파이트 및 혼합 알킬아릴포스포르아미드중에서 선택되고 바람직하게는 트리에틸포스파이트인 방법.
  3. 제2항에 있어서, 일반식(II)화합물 몰당 트리알킬 포스파이트 2몰당량을 사용하고 반응을 20 내지 80℃, 바람직하게는 40 내지 60℃온도에서 시행하는 방법.
  4. 제1항 내지 3항중의 어느하나에 있어서, 다음 일반식(III)의 화합물을 일반식(IV)인 산의 반응성 유도체 바람직하게는 그의 할라이드와 불활성 용매 바람직하게는 할로겐화 탄화수소 용매중 유기염기 바람직하게는 3급아민 존재하에, 산 할라이드를 사용할 경우에는 임의로 할로겐화 수소 경합제를 사용하여 반응시켜 제조된 일반식(II)화합물을 사용하는 방법.
    상기 식중, R1,R2, X, Z 및 R3는 제1항의 일반식(II)에서 정의된 바와 같다.
  5. 제4항에 있어서, 일반식(III)화합물을 일반식(IV)인 산의 반응성 유도체 및 언급된 3급아민 대략 1몰당량(일반식III)의 화합물 몰당), 할로겐화 수소 결합제를 사용할 경우에는 적어도 1몰 당량과 언급된 불활성 용매중에서 혼합함을 특징으로 하는 방법.
  6. 제4항 또는 5항에 있어서, 일반식(IV)의 산할라이드가 알릴옥시 옥살릴클로라이드 또는 바람직하게는 클로로알릴옥시옥살릴클로라이드이며 3급 아민이 디이소프로필에틸아민이고 결합제는 탄산칼슘인 방법.
  7. 제1항 내지 6항중의 어느하나에 있어서, X가 황, -(-CH2-)n- 또는 잔기=NR7(이때 n 및 R7은 1항에서 정의된 바와 같음)인 방법.
  8. 제7항에 있어서, X 및 Z가 모두 S이고, R1이이며, R2가 저급알킬이고 R3가 -COOR6(이때 R6는 아릴 또는 바람직하게는 클로로알릴)인 일반식(I)화합물을 제조하는 방법.
  9. 제1항 내지 7항중의 어느하나에 있어서 X가 (CH2)이고, Z가 S이며 R1이 CH3-CH-OR5이고 R2가 N-보호아미노에틸이며, R2가 -COOR6인 (이때 R5및 R6는 제1항에서 정의된 바와 같음) 일반식(I)의 화합물을 제조하는 방법.
  10. 제1항 내지 8항중의 어느하나에 있어서, R3중의 보호그룹을 제거시키고, R3가 -COOR6일 경우에는 (이때 R6는 알킬, 아릴 또는 알릴릭그룹) R1, R2및 R7중의 보호그룹을 제거시키는 방법.
  11. 제10항에 있어서, 나트륨 또는 칼륨(5R, 6S, 8R)-6-(1-하이드록시에틸)-2-에틸티오-페넴-3-카복실레이트 또는 나트륨 또는 칼륨(5R, 6S, 8R)-6-(1-하이드록시에틸)-2-메틸티오-페넴-3-카복실레이트를 제조하는 방법.
  12. 일반식(V)의 화합물 또는 그의 약제학적으로 허용되는 염.
    상기식에서 R1, R2, R3, X 및 Z는 제1항에서 정의된 바와 같으나, 단, (i) Z 및 X는 동시에 n이 1 또는 2인 -(CH2)n-이 될 수 없으며; (ii) X가 S일때는 Z는 0또는 =NR7이며; (iii) X가 O일때는 Z는 O, S 또는 =NR7이며; (iv) X가 -CH2-이면 Z는 =NR7이나, R7이 H 또는 저급알킬이고 R2가 저급알킬이면 R1은 아실아미노가 될 수 없으며; (v) X가 -(-CH2-)2-이면, Z는 =NR7이어야 한다(상기에서 R7은 제1항에서 정의된 바와 같다).
  13. 제12항에 있어서, X가 =NR7인 화합물 및 그의 약제학적으로 허용되는 염.
  14. 제12항에 있어서, 일반식(VI)의 화합물 및 그의 약제학적으로 허용되는 염.
    상기 식중 G는 저급알콕시 또는 그룹이고 R2, R3및 R7은 제12항에서 정의된 바와 같다.
  15. 제12항에 있어서, 일반식(VII)의 화합물 및 그의 약제학적으로 허용되는 염.
    상기식중, Z, R2및 R3는 제12항에서 정의된 바와 같고 이때 R3는 바람직하게는 -COOR6이며 R6는 제1항에서 정의된 바와 같다.
  16. 제12항 내지 15항중의 어느 하나에 있어서, R1이 하이드록시 보호그룹 또는 N-보호그룹 또는 S-보호그룹을 함유하고 및/또는 R2가 0-보호그룹 또는 N-보호그룹을 함유하며 및/또는 R7이 N-보호그룹이고 R3는 니트릴, 테트라졸릴 또는 -COOR6(이때 R6는 수소 또는 대사성 에스테르 그룹중에서 선택됨)인 화합물 및 그의 약제학적으로 허용되는 염.
  17. 제12항 내지 16항중의 어느 하나에서 정의된 화합물 또는 그의 약제학적으로 허용되는 염을 약제학적으로 허용되는 담체 또는 부형제와 혼합 함유함을 특징으로 하는 약제학적 조성물.
  18. 제12항 내지 16항중의 어느 하나에 있어서, 세균감염증 치료에 사용되는 화합물 또는 약제학으로 허용되는 염.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8200375A 1981-02-02 1982-01-29 2-페넴 화합물의 제조방법 KR880001774B1 (ko)

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US230774 1981-02-02
US06/230,774 US4347183A (en) 1981-02-02 1981-02-02 Process for the synthesis of penems and carbapenems

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EP (2) EP0162193A1 (ko)
JP (1) JPS57146777A (ko)
KR (1) KR880001774B1 (ko)
AT (1) ATE21699T1 (ko)
AU (1) AU557691B2 (ko)
DE (1) DE3272792D1 (ko)
DK (1) DK160877C (ko)
FI (1) FI74966C (ko)
HU (1) HU189559B (ko)
IE (1) IE54214B1 (ko)
IL (1) IL64905A (ko)
NO (1) NO159795C (ko)
NZ (1) NZ199599A (ko)
PH (1) PH21195A (ko)
PT (1) PT74356B (ko)
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Also Published As

Publication number Publication date
PH21195A (en) 1987-08-19
JPS57146777A (en) 1982-09-10
FI74966C (fi) 1988-04-11
PT74356B (en) 1984-05-30
EP0058317A1 (en) 1982-08-25
NZ199599A (en) 1985-11-08
DK38982A (da) 1982-08-03
ATE21699T1 (de) 1986-09-15
IL64905A (en) 1986-04-29
EP0162193A1 (en) 1985-11-27
ZA82567B (en) 1983-01-26
EP0058317B1 (en) 1986-08-27
DE3272792D1 (en) 1986-10-02
FI820281L (fi) 1982-08-03
AU557691B2 (en) 1987-01-08
IL64905A0 (en) 1982-04-30
NO159795C (no) 1989-02-08
DK160877C (da) 1991-10-14
IE820211L (en) 1982-08-02
KR880001774B1 (ko) 1988-09-15
HU189559B (en) 1986-07-28
AU7991782A (en) 1982-08-12
FI74966B (fi) 1987-12-31
NO159795B (no) 1988-10-31
DK160877B (da) 1991-04-29
IE54214B1 (en) 1989-07-19
PT74356A (en) 1982-02-01
NO820264L (no) 1982-08-03
US4347183A (en) 1982-08-31

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