KR910002817A - 항균제로서 유용한 아미노메틸옥소옥사졸리디닐 아릴벤젠 유도체 - Google Patents

항균제로서 유용한 아미노메틸옥소옥사졸리디닐 아릴벤젠 유도체 Download PDF

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KR910002817A
KR910002817A KR1019890010984A KR890010984A KR910002817A KR 910002817 A KR910002817 A KR 910002817A KR 1019890010984 A KR1019890010984 A KR 1019890010984A KR 890010984 A KR890010984 A KR 890010984A KR 910002817 A KR910002817 A KR 910002817A
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phenyl
ylmethyl
acetamide
alkyl
compound according
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켄트 칼슨 랜덜
박 정호
아델만 그레고리 월터
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제임스 제이. 플린
이. 아이. 듀퐁 드 네모아 앤드 캄파니
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    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • 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
    • C07D263/24—Oxygen atoms attached in position 2 with hydrocarbon radicals, substituted by oxygen atoms, attached to other ring carbon atoms
    • 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
    • C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole 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
    • 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
    • C07D413/02—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
    • C07D413/10—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 aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings

Abstract

내용 없음.

Description

항균제로서 유용한 아미노메틸옥소옥사졸리디닐 아릴벤젠 유도체.
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (44)

  1. 일반식(I)의 아릴 벤젠 옥사졸리디논 또는 이의 약학적으로 허용되는 염.
    상기식에서 화합물의 ℓ 및 d 및 ℓ입체이성체의 혼합물의 경우, Ar은
    X 및 Y로 임의 치환된 디아지닐 그룹, X 및 Y로 임의 치환된 트리아질 그룹,
    중에서 선택된 방향족 그룹이고;
    Z는 산소, S, 또는 NR5이며, W는 CH 또는 N이거나 Z가 NR5인 경우 또한 S 또는 산소이고, X는 독립적으로 N, -NO2, -S(O)nR1, 테트라조일, -S(O)2-N=S(O)PR2R3, -SH,, -COR23, -CONR5R6, , 할로겐, -NR5R6, , α위치가 아닌 위치에서 하나 이상의 할로겐 원자, OH, =0로 임의 치환된 탄소수 1내지 8의 알킬, S(0)nR24, 또는 NR5R6, 탄소수 2내지 5의 알케닐 또는 탄소수 3내지 8의 사이클로알킬이며, R1은 하나 이상의 할로겐 원자, OH, CN, NR4R6또는 CO2R8로 임의 치환된 C1-C4알킬, C2-C4알케닐 -NR9R10, -N3,,-NG2, NR9G 또는 --NGM+이고, R2및 R3는 독립적으로 C1-C2알킬이거나, 함께는 -(CH2)g-이고, R4는 하나 이상의 할로겐으로 임의 치환된 탄소수 1내지 4의 알킬이고, R5및 R6는 독립적으로, H 탄소수 1내지 8의 알킬 탄소수 3내지 8의 사이클로 알킬, -(CH2)tOR8, -(CH2)tNR11R11a, 또는 -O(CH2)tot8, -(CH2)tNR11R11a, 또는 -O(CH2)tNR11R11a 이거나 함께는 -(CH2)2O(CH2)2-,-(CH2)tCH(COR1)-, 또는이며, R7은 -NR5R6, -OR5또는이고, R8은 H또는 탄소수 1내지 4의 알킬이며, R9은 H, C1-C4알킬 또는 C3-C8사이클로알킬이고, R10은 C1-C4알킬, C2-C4알케닐, C3-C4사이클로알킬, -Or8또는 -NR11R11A이며, R11및 R11A 는 독립적으로 H 또는 C1-C4알킬이거나, 함게는 -(CH2)r-이고, G는 Cl, Br 또는 I이며, Y는 독립적으로 H, F, Cl, Br, OR8, 탄소수 1내지 3의 알킬, 또는 NO2이고, X 및 Y는 함께 (a)Ar이또는인 경우 융합된 6-원 카르보사이클릭 환을 형성하거나, (b)인 경우,을 형성하며, M은 생리적으로 허용되는 양이온이고, n은 0,1또는 2이고, p는 0또는 1이고, q는 3, 4또는 5이고, r는 4또는 5이고, t는 1, 2 또는 3이고, B는 -NH2, 또는 N3이며, R12는 H, C1-C10알킬 또는 C3-C8사이클로알킬이고, R13는 H, 하나 이상의 할로겐원자로 임의 치환된 C1-C4알킬, C2-C4알케닐, C3-C4사이클로알킬, 페닐, -CH2OR15, -CH(OR16) OR17, -CH2S(O)rR11,, -OR17, -SR14, -CH2N8, 글리신, L-알라닌, L-시스테인, L-프룰린, 및 D-알라닌과 같은 α-아미노산으로부터 유도된 아미노알킬 그룹, -NR19R20또는 -C(NH2)R21R22이며, R14는 하나이상의 할로겐 원자로 임의 치환된 C1-C4알킬이고, R15는 H이거 하나 이상의 할로겐 원자로 임의 치환된 C1-C4알킬이며, R16및 R17은 독립적으로 C1-C4알킬이거나, 함께는 -(CH2)m-이고, R18은 C1-C4알킬 또는 C7-C11아르알킬이며, R19및 R20은 독립적으로 H 또는 C1-C2알킬이고, R21및 R22는 독립적으로 H, C1-C4알 C3-C6사이클로알킬, 페닐이거나, 함께는 -(CH2)5-이며, u는 1또는 2이고, V는 0, 1또는 2이며, m은 2또는 3이고, S는 2, 3, 4또는 5이며, R23은 H, 하나 이상의 할로겐으로 임의 치환된 탄소수 1내지 8의 알킬, 탄소수 3내지 8의 사이클로알킬, -S(O)mR24, -OR8,, 또는 -NR5R8중 하나 이상으로 치환된 탄소수 1내지 4의 알킬이거나, CHO 또는 CO2R8로의 임의 치환된 탄소수2내지5의 알케닐이고, R24는 탄소수 1내지 4의 알킬 또는 탄소수 3내지8의 사이클로알킬이며, R25는 R6또는 NR5R6이고, 단, 1)B가 NH2인 경우, Ar은 할로겐 또는 CF3로 임의 치환된 페닐이 아니다.
  2. 제1항 있어서, B가(여기서, R13은 H, CH3, -OR18, CH2Cl, CH2OH, 또는 CH2OCH3이다) 인옥사졸리디논.
  3. 제2항에 있어서, B가인 옥사졸리디논,
  4. 제1항에 있어서, Ar이또는인 옥사졸리디논.
  5. 제4항에 있어서, Y가 H인 옥사졸리디논,
  6. 제5항에 있어서, X가 H, 탄소수 1내지 5의 알킬, -S(O)nCH3(여기서, n은 0.1 또는 2이다),-OR5, -CH2NR5R6, R6R5N(CH2)2(CH(OH)-, 또는 -CN인 옥사졸리디논.
  7. 제3항에 있어서, Ar이또는
    인 옥사졸리디논.
  8. 제7항에 있어서, Y가 H인 옥사졸리디논.
  9. 제8항에 있어서, X가 H, 탄소수 1내지 5의 알킬, -S(O)nCH3(여기서, n은 0.1또는 2이다),,-OR5, -CH2NR5R6, R6R5N(CH2)2(CH(OH)-, 또는 -CN인 옥사졸리디논.
  10. 제7항에 있어서, (ℓ)-N-[3-(4-페닐페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  11. 제7항에 있어서, (ℓ)-N-[3-{4-(4′-아세틸페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  12. 제7항에 있어서, (ℓ)-N-[3-(4-(4′-메틸술피닐페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  13. 제7항에 있어서, (ℓ)-N-[3-(4-(4′-메탄술포닐페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  14. 제7항에 있어서, (ℓ)-N-[3-(4-(4′-시아노페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  15. 제7항에 있어서, (ℓ)-N-[3-(4-(4′-디에틸 아미노메틸페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  16. 제7항에 있어서, (ℓ)-N-[3-(4-(4′-디-n-프로필아미노메틸페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  17. 제7항에 있어서, (ℓ)-N-[3-(4-(4′-(3-N,N-디메틸아미노-1-하이드록시프로필)페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  18. 제7항에 있어서, (ℓ)-N-[3-(4-(4′-(1-하이드록시-3-(4-모르폴리닐)-프로필)페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드인 옥사졸리디논.
  19. 제7항에 있어서, (ℓ)-N-[3-(4-(4′-피리딜페닐페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, 하이드로클로라이드인 옥사졸리디논.
  20. 제7항에 있어서, (ℓ)-N-[3-(4-(3′-피리딜페닐페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, 하이드로클로라이드인 옥사졸리디논.
  21. 적합한 약학적 담체 및 제1항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  22. 적합한 약학적 담체 및 제2항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  23. 적합한 약학적 담체 및 제3항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  24. 적합한 약학적 담체 및 제4항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  25. 적합한 약학적 담체 및 제5항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  26. 적합한 약학적 담체 및 제6항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  27. 적합한 약학적 담체 및 제7항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  28. 적합한 약학적 담체 및 제8항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  29. 적합한 약학적 담체 및 제9항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  30. 적합한 약학적 담체 및 제10항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  31. 적합한 약학적 담체 및 제11항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  32. 적합한 약학적 담체 및 제12항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  33. 적합한 약학적 담체 및 제13항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  34. 적합한 약학적 담체 및 제14항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  35. 적합한 약학적 담체 및 제15항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  36. 적합한 약학적 담체 및 제16항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  37. 적합한 약학적 담체 및 제17항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  38. 적합한 약학적 담체 및 제18항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  39. 적합한 약학적 담체 및 제19항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  40. 적합한 약학적 담체 및 제20항에 따른 화합물의 유효량을 함유하는 약학적 조성물.
  41. 제1항에 따른 화합물의 항균량을 포유동물에게 투여함을 특징으로 하여, 포유동물에서 세균성 감염을 치료하는 방법.
  42. 제7항에 따른 화합물의 항균량을 포유동물에게 투여함을 특징으로 하여, 포유동물에서 세균성 감염을 치료하는 방법.
  43. (a) (ℓ)-N-[3-(4-페닐페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (b) (ℓ)-N-[3-(4-(4′-아세틸페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (c) (ℓ)-N-[3-(4-(4′-메틸슬피닐페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (d) (ℓ)-N-[3-(4-(4′-메틸술피닐페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (c) (ℓ)-N-[3-(4-(4′-시아노페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (f) (ℓ)-N-[3-(4-(4′-디에틸아미노메틸페닐)-페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (g) (ℓ)-N-[3-(4-(4′-디-n-프로필아미노메틸페닐)-페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (h) (ℓ)-N-[3-(4-(4′-(3-N,N-디메틸아미노-1-하이드록시페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (i) (ℓ)-N-[3-(4-(4′-(1-하이드록시-3-(4-모르포릴)-프로필)페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, (j) (ℓ)-N-[3-(4-(4′-피리딜페닐)-페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, 하이드로클로라이드, (k) (ℓ)-N-[3-(4-(3′-피리딜페닐)페닐)-2-옥소옥사졸리딘-5-일메틸]아세트아미드, 하이드로클로라이드 중에서 선택된 화합물이 항균량을 포유동물에게 투여함을 특징으로 하여, 포유동물에서 세균성 감염을 치료하는 방법.
  44. (1) 일반식(ⅩⅩⅦ)의 카복실산을 메틸 클로로포메이트, 이어서 나트륨 아지드와 반응시켜 일반식(ⅩⅩⅨ)의 아실아지드를 제조하고, (2)일반식(ⅩⅩⅨ)의 화합물을 글리시딘아지드와 반응시켜 B가 N3인 일반식(I)의 옥사졸리디논을 제조하고, (3)단계(2)로 부터의 일반식(I)의 화합물을 수소와 반응시켜 B가 NH2인 상응하는 화합물을 제조하고, 및 임의로는 (4)단계(3)에서 제조된 화합물을 아세틸 클로라이드와 반응시켜 B가인 상응하는 화합물을 제조함을 특징으로 하여, 제1항에 따른 화합물을 제조하는 방법.
    상기식에서, Ar은 제1항에서 정의한 바와 같다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019890010984A 1988-07-29 1989-07-29 항균제로서 유용한 아미노메틸옥소옥사졸리디닐 아릴벤젠 유도체 KR910002817A (ko)

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US07/225,809 US4948801A (en) 1988-07-29 1988-07-29 Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents

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FR2356422A1 (fr) * 1976-03-01 1978-01-27 Delalande Sa Nouveaux hydroxymethyl-5 oxazolidinone-2, leur procede de preparation et leur application en therapeutique
FR2500450A1 (fr) * 1981-02-25 1982-08-27 Delalande Sa Nouveaux derives aminomethyl-5 oxazolidiniques, leur procede de preparation et leur application en therapeutique
ES8506659A1 (es) * 1983-06-07 1985-08-01 Du Pont Un procedimiento para la preparacion de nuevos derivados del amino-metil-oxooxazolidinil-benzeno.
CA1260948A (en) * 1984-12-05 1989-09-26 E. I. Du Pont De Nemours And Company Aminomethyl oxooxazolidinyl benzene derivatives useful as antibacterial agents
US4801600A (en) * 1987-10-09 1989-01-31 E. I. Du Pont De Nemours And Company Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents
CA1320730C (en) * 1987-10-16 1993-07-27 The Du Pont Merck Pharmaceutical Company Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents
ES2059467T3 (es) * 1987-10-21 1994-11-16 Du Pont Merck Pharma Derivados de aminometil-oxooxazolidinil-etenilbenceno utiles como agentes antibacterianos.

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FI893618A (fi) 1990-01-30
US4948801A (en) 1990-08-14
AU622465B2 (en) 1992-04-09
NO893076L (no) 1990-01-30
IL91129A0 (en) 1990-03-19
MY104096A (en) 1993-11-30
NZ230108A (en) 1991-10-25
ZA895778B (en) 1991-03-27
JP2899319B2 (ja) 1999-06-02
PT91315A (pt) 1990-02-08
FI893618A0 (fi) 1989-07-28
AU3911589A (en) 1990-02-01
DK374389D0 (da) 1989-07-28
DK374389A (da) 1990-01-30
NO893076D0 (no) 1989-07-28
HUT58062A (en) 1992-01-28
CA1337526C (en) 1995-11-07
IE892438L (en) 1990-01-29
EP0352781A2 (en) 1990-01-31
EP0352781A3 (en) 1990-07-11
JPH02124877A (ja) 1990-05-14

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