KR970703340A - 과혈당 치료제로서의 신규한 아졸리딘디온(New azolidinediones as antihyperglycemic agents) - Google Patents

과혈당 치료제로서의 신규한 아졸리딘디온(New azolidinediones as antihyperglycemic agents) Download PDF

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KR970703340A
KR970703340A KR1019960706490A KR19960706490A KR970703340A KR 970703340 A KR970703340 A KR 970703340A KR 1019960706490 A KR1019960706490 A KR 1019960706490A KR 19960706490 A KR19960706490 A KR 19960706490A KR 970703340 A KR970703340 A KR 970703340A
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phenyl
methyl
dione
oxazol
ylmethoxy
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마이클 소티오리오스 말라마스
이완 구나완
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슬레이터 티모씨 티
아메리칸 홈 프로덕츠 코포레이션
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    • 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
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    • C07D263/34—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 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
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    • 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
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    • C07D417/12—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 chain containing hetero atoms as chain links
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    • 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
    • C07D417/14—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 three or more hetero rings

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Abstract

본 발명은 당료성 ob/ob 및 db/db 마우스, 즉 비-인슐린 의존성 당료병(NIDDM 또는 타임 II 당료병)의 동물 모델에서 경구적 과혈당 치료 활성이 입증된 신규한 화학식 (I)의 화합물 또는 이의 약제학적으로 허용되는 염에 관한 것이다.
상기 식에서, R1은 C1-C6알킬, C3-C8사이클로알킬, 티에닐, 푸릴, 피리딜,
R10은 수소, C1-C6알킬, 불소, 염소, 브롬, 요오드, C1-C6알킬옥시, 트리플루오로알킬 또는 트리플루오로알콕시이며, R2는 수소 또는 C1-C6알킬이고, X는 O 또는 S이며, n은 0, 1 또는 2이고,
R3은 수소, C1-C6알킬, 할로겐, C1-C6알콕시, 트리플루오로알킬 또는 트리플루오로알콕시이고,
R4는 수소, C1-C6알킬, 알릴, C6-C10아릴, C6-C10아릴-(CH2)1-6-, 불소, 염소, 브롬, 요오드, 트리메틸실릴 또는 C3-C8사이클로알킬이고, R5는 수소, C1-C6알킬, C6-C10아릴 또는 C6-C10아릴 또는 C6-C10아릴-(CH2)1-6-이며, m은 0,1 또는 2이고, R6은 수소 또는 C1-C6알킬이며, R7은 수소 또는 C1-C6알킬이고, R8및 R9는 독립적으로 수소, C1-C6알킬, 불소, 염소, 브롬 또는 요오드중에서 선택되며, Y는 O 또는 S이고, Y가 O일때 Z는 N 또는 CH이며, Y가 S일 때 Z는 CH이다.

Description

과혈당 치료제로서의 신규한 아졸리딘디온(New azolidinediones as antihyperglycemic agents)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. 하기 화학식(I)의 화합물 또는 이의 약제학적으로 허용되는 염.
    상기 식에서, R1은 C1-C6알킬, C3-C8사이클로알킬, 티에닐, 푸릴, 피리딜,
    이고,
    R10은 수소, C1-C6알킬, 불소, 염소, 브롬, 요오드, C1-C6알킬옥시, 트리플루오로알킬 또는 트리플루오로알콕시이며, R2는 수소 또는 C1-C6알킬이고, X는 O 또는 S이며, n은 0, 1 또는 2이고,
    R3은 수소, C1-C6알킬, 할로겐, C1-C6알콕시, 트리플루오로알킬 또는 트리플루오로알콕시이고,
    R4는 수소, C1-C6알킬, 알릴, C6-C10아릴, C6-C10아릴-(CH2)1-6-, 불소, 염소, 브롬, 요오드, 트리메틸실릴 또는 C3-C8사이클로알킬이고, R5는 수소, C1-C6알킬, C6-C10아릴 또는 C6-C10아릴 또는 C6-C10아릴-(CH2)1-6-이며, m은 0,1 또는 2이고, R6은 수소 또는 C1-C6알킬이며, R7은 수소 또는 C1-C6알킬이고, R8및 R9는 독립적으로 수소, C1-C6알킬, 불소, 염소, 브롬 또는 요오드중에서 선택되며, Y는 O 또는 S이고, Y가 O일때 Z는 N 또는 CH이며, Y가 S일 때 Z는 CH이다.
  2. 제1항에 있어서, 화학식(Ia)의 화합물 또는 그의 약제학적으로 허용되는 염.
    상기 식에서, R10은 수소, C1-C6알킬, 불소, 염소, 브롬, 요오드, C1-C6알킬시, 트리플루오로알킬 또는 트리플루오로알콕시이고, n은 1 또는 2이며,
    m은 0, 1 또는 2이고, R4, R5, R6및 R7은 독립적으로 수소 또는 C1-C6알킬이며, Y는 O 또는 S이고, Z는 Y가 O일 때 N 또는 CH이고, Y가 S일 때 CH이다.
  3. 제3항에 있어서, 화학식(Ib)의 화합묠 또는 이의 약제학적으로 허용되는 염.
    상기 식에서, R10은 수소, CF3-, CF3O-, CF3CH2O- 또는 Cl-이고, n은 1 또는 2이며,
    m은 0 또는 1이고, R4, R5, R6및 R7은 독립적으로 수소, 메틸 또는 에틸이며, Y는 O 또는 S이고, Z는 Y가 O일 때 N 또는 CH이고, Y가 S일 때 CH이다.
  4. 제3항에 있어서, (E)-2-(3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐)-펜트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (Z)-2-(3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐)-펜트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-(3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메틸]-페닐}-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(3-{3-[5-메틸-2-(4-트리플루오로메톡시-페닐)-옥사졸-4-일메톡시]-페닐}-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(3-{3-[5-메틸-2-(4-트리플루오로-에톡시-페닐)-옥사졸-4-일메톡시]-페닐}-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-{3-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시)-페닐]-부트-2-에닐}-[1,2,4]옥사디아졸리딘-3,5-디온, (Z)-2-{3-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시]-페닐]-부트-2-에닐-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-{3-[3-[2-(5-메틸-2-페닐-옥사졸-4-일)-에톡시]-페닐-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-{3-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시]-벤조푸란-5-일]-부트-2-에닐-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(2-메틸-3-{4-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일에톡시]-페닐-에닐-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(2-에틸-3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-알릴}-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(1-메틸-3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐-알릴)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(3-(3-[2-(4-클로로-페닐)-5-메틸-옥사졸-4-일메톡시]-페닐}-1-메틸-알릴)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(2-메틸-3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (Z)-2-(2-메틸-3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-[1-메틸-3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-[3-(4-{4-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-알릴)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-2-{3-[5-메틸-2-(4-트리플루오로메틸)-페닐)-옥사졸-4-일메톡시]-페닐-사이클로프로필메틸)-[1,2,4]옥사졸리딘-3,5-디온, (E)-2-(2-메틸-2-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-사이클로프로필메틸)-[1,2,4]옥사디아졸리딘-3,5-디온, (E,E)-2-{5-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시]-페닐}-헥사-2,4-디에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (Z,E)-2-{5-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시]-페닐}-헥사-2,4-디에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-[3-(4-(2-[5-메틸-2-(4-트리플루오로에틸-페닐-옥사졸-4-일]-에톡시}-페닐)-프로필-2-이닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-{1-메틸-3-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시)-페닐]-프로필-2-이닐}-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-5-{3-[3-(5-메틸-2-페닐-옥사졸-4-일메틸]-페닐]-부트-2-에닐}-옥사졸리딘-2,4-디온, (E)-5-[3-(3-{5-메틸-2-[4-(2,2,2-트리플루오로-에톡시)-페닐]-옥사졸-4-일메톡시]-페닐)-부트-2-에닐]-옥사졸리딘-2,4-디온, (E)-5-(3-{3-[5-메틸-2-(트리플루오로메톡시-페닐)-옥사졸-4-일메톡시]-페닐]-부트-2-에닐)-옥사졸리딘-2,4-디온, (E)-5-(3-{3-[2-(5-메틸-2-페닐)-옥사졸-4-일)-에톡시]페닐}-부트-2-에닐)-옥사졸리딘-2,4-디온, (E)-5-{3-[3-(5-메틸-2-페닐)-옥사졸-4-일메톡시]-페닐]-부트-2-에닐)-티아졸리딘-2,4-디온 및 (E)-5-(3-{3-[5-메틸-2-(4-트리플루오로메톡시-페닐)-옥사졸-4-일메톡시]-페닐}-부트-2-에닐-티아졸리딘-2,4-디온으로 이루어진 그룹중에서 선택된 화합물.
  5. 치료학적 유효량의 화학식(I)의 화합물 또는 이의 약제학적으로 허용되는 염을 비-인슐린 의존성 당뇨병을 앓는 포유동물에게 투여함을 포함하여, 상기 포유동물에서 비-인슐린 의존성 당뇨병의 과혈당증을 치료하는 방법.
    상기 식에서, R1은 C1-C6알킬, C3-C8사이클로알킬, 티에닐, 푸릴, 피리딜,
    R10은 수소, C1-C6알킬, 불소, 염소, 브롬, 요오드, C1-C6알킬옥시, 트리플루오로알킬 또는 트리플루오로알콕시이며, R2는 수소 또는 C1-C6알킬이고, X는 O 또는 S이며, n은 1 또는 2이고,
    R3은 수소, C1-C6알킬, 할로겐, C1-C6알콕시, 트리플루오로알킬 또는 트리플루오로알콕시이고,
    R4는 수소, C1-C6알킬, 알릴, C6-C10아릴, C6-C10아릴-(CH2)1-6-, 불소, 염소, 브롬, 요오드, 트리메틸실릴 또는 C3-C8사이클로알킬이고, R5는 수소, C1-C6알킬, C6-C10아릴-(CH2)1-6-이며, m은 0, 1 또는 2이고, R6은 스소 또는 C1-C6알킬이며, R7은 수소 또는 C1-C6알킬이고, R8및 R9는 독립적으로 수소, C1-C6알킬, 불소, 염소, 브롬 또는 요오드중에서 선택되며, Y는 O 또는 S이고, Z는 Y가 O일때 N 또는 CH이며, Y가 S일 때, CH이다.
  6. 제5항에 있어서, 사용된 화합물이 화학식(Ia)의 화합물 또는 그의 약제학적으로 허용되는 염인 치료방법.
    상기 식에서, R10은 C1-C6알킬, 불소, 염소, 브롬, 요오도, C1-C6알콕시, 트리플루오로알킬 또는 트리플루오로알콕시이고, n은 1 또는 2이며,
    m은 0, 1 또는 2이고, R4, R5, R6및 R7은 독립적으로 수소 또는 C1-C6알킬이며, Y는 O 또는 S이고, Z는 Y가 O일 때 N 또는 CH이고, Y가 S일 때 CH이다.
  7. 제6항에 있어서, 사용된 화합물이 화학식(Ib)의 화합물 또는 이의 약제학적으로 허용되는 염인 치료방법.
    상기 식에서, R10은 수소, CF3-, CF3O-, CF3CH2O- 또는 Cl-이고, n은 1 또는 2이며,
    m은 0 또는 1이고, R4, R5,R6및 R7은 독립적으로 수소, 메틸 또는 에틸이며, Y는 O 또는 S이고, Z는 Y가 O일 때 N 또는 CH이며, Y가 S일 때 CH이다.
  8. 제7항에 있어서, 사용된 화합물이 (E)-2-(3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-펜트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (Z)-2-(3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐-펜트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-(3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메틸]-페닐}-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(3-{3-[5-메틸-2-(4-트리플루오로메톡시-페닐)-옥사졸-4-일메톡시]-페닐)-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(3-{3-[5-메틸-2-(4-트리플루오로-에톡시-페닐)-옥사졸-4-일메톡시]-페닐}-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(3-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시)-페닐]-부트-2-에닐-[1,2,4]옥사디아졸리딘-3,5-디온, (Z)-2-{3-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시]-페닐]-부트-2-에닐}-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-{3-[3-[2-(5-메틸-2-페닐-옥사졸-4-일)-에톡시]-페닐-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-{3-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시]-벤조푸란-5-일]-부트-2-에닐}-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(2-메틸-3-{4-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐-알릴}-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(2-에틸-3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-알릴-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(1-메틸-3-{3-[5-메틸-2-[4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-알릴)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(3-(3-[2-(4-클로로-페닐)-5-메틸-옥사졸-4-일메톡시]-페닐-1-메틸-알릴)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(2-메틸-3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (Z)-2-(2-메틸-3-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(l-메틸-3-(3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐-부트-2-에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-[3-(4-{4-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-알릴)-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-2-(2-{3-[5-메틸-2-(4-트리플루오로메틸)-페닐)-옥사졸-4-일메톡시]-페닐}-사이클로프로필메틸)-[1,2,4]옥사졸리딘-3,5-디온, (E)-2-(2-메틸-2-{3-[5-메틸-2-(4-트리플루오로메틸-페닐)-옥사졸-4-일메톡시]-페닐}-사이클로프로필메틸)-[1,2,4]옥사디아졸리딘-3,5-디온, (E,E)-2-{5-[3-(5-메틸-2-페닐-옥사졸-4-메톡시]-페닐}-헥사-2,4-디에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, (Z,E)-2-{5-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시]-페닐-헥사-2,4-디에닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-[3-(4-{2-[5-메틸-2-(4-트리플루오로메틸-페닐-옥사졸-4-일]-에톡시}-페닐)-프로필-2-이닐)-[1,2,4]옥사디아졸리딘-3,5-디온, 2-{1-메틸-3-[3-(5-메틸-2-페닐-옥사졸-4-일메톡시)-페닐]-프로필-2-이닐-[1,2,4]옥사디아졸리딘-3,5-디온, (E)-5-{3-[3-(5-메틸-2-페닐-옥사졸-4-일메틸]-페닐]-부트-2-에닐-옥사졸리딘-2,4-디온, (E)-5-[3-(3-{5-메틸-2-[4-(2,2,2-트리플루오로-에톡시)-페닐]-옥사졸-4-일메톡시}-페닐)-부트-2-에닐]-옥사졸리딘-2,4-디온, (E)-5-(3-{3-[5-메틸-2-(트리플루오로메톡시}-페닐)-옥사졸-4-일메톡시]-페닐-부트-2-에닐)-옥사졸리딘-2,4-디온, (E)-5-(3-{3-[2-(5-메틸-2-페닐)-옥사졸-4-일)-에톡시]페닐}-부트-2-에닐)-옥사졸리딘-2,4-디온, (E)-5-{3-[3-(5-메틸-2-페닐)-옥사졸-4-일메톡시]-페닐-부트-2-에닐)-티아졸리딘-2,4-디온 및 (E)-5-(3-{3-[5-메틸-2-(4-트리플루오로메톡시-페닐)-옥사졸-4-일메톡시]-페닐}-부트-2-에닐)-티아졸리딘-2,4-디온으로 이루어진 그룹중에서 선택되는 치료 방법.
  9. 약제학적 담체 및 치료학적 유효량의 화학식 (I)의 화합물 또는 이의 약제학적으로 허용되는 염을 포함하는, 모유동물의 과혈당증 치료용 약제학적 조성물.
    상기 식에서, R1은 C1-C6알킬, C3-C8사이클로알킬, 티에닐, 푸릴, 피리딜,
    R10는 수소, C1-C6알킬, 불소, 염소, 브롬, 요오드, C1-C6알킬옥시, 트리플루오로알킬 또는 트리플루오로알콕시이며, R2는 수소 또는 C1-C6알킬이고, X는 O 또는 S이며, n은 1 또는 2이고,
    R3은 수소, C1-C6알킬, 할로겐, C1-C6알콕시, 트리플루오로알킬 또는 트리플루오로알콕시이고,
    R4는 수소, C1-C6알킬, 알릴, C6-C10아릴, C6-C10아릴-(CH2)1-6-, 불소, 염소, 브롬, 요오도, 트리메틸실릴 또는 C3-C8사이클로알킬이고, R5는 수소, C1-C6알킬, C6-C10아릴 또는 C6-C10아릴-(CH2)1-6-이며, m은 0, 1 또는 2이고, R6은 수소 또는 C1-C6알킬이며, R7은 수소 또는 C1-C6알킬이고, R8및 R9는 독립적으로 수소, C1-C6알킬, 불소, 염소, 브롬 또는 요오드 중에서 선택되며, Y는 O 또는 S이고, Z는 Y가 O일때, N 또는 CH이며, Y가 S일 때 CH이다.
    ※ 참고사항:최초출원 내용에 의하여 공개하는 것임.
KR1019960706490A 1994-05-18 1995-04-13 과혈당 치료제로서의 신규한 아졸리딘디온(New azolidinediones as antihyperglycemic agents) KR970703340A (ko)

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TW328089B (en) 1998-03-11
WO1995031454A1 (en) 1995-11-23
HUT76823A (en) 1997-11-28
US5468762A (en) 1995-11-21
ATE173256T1 (de) 1998-11-15
ZA953981B (en) 1996-11-18
DK0759919T3 (da) 1999-07-26
EP0759919B1 (en) 1998-11-11
US5510360A (en) 1996-04-23
CA2190015A1 (en) 1995-11-23
DE69505968D1 (de) 1998-12-17
NZ284654A (en) 1998-12-23
AU684357B2 (en) 1997-12-11
CN1152312A (zh) 1997-06-18
AU2384295A (en) 1995-12-05
HU9603185D0 (en) 1997-01-28
EP0759919A1 (en) 1997-03-05
ES2124545T3 (es) 1999-02-01
JPH10500133A (ja) 1998-01-06
DE69505968T2 (de) 1999-05-12
GR3029355T3 (en) 1999-05-28

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