KR950701621A - 아실 조효소a : 콜레스테롤 아실 전이효소(acat)의 억제제로서 신규한 n- 아릴 및 n- 헤테로아릴우레아 유도체(new n-aryl and n-heteroarylurea derivatives as inhibitors of acyl coenzyme a : cholesterol acyl transferase(acat) - Google Patents

아실 조효소a : 콜레스테롤 아실 전이효소(acat)의 억제제로서 신규한 n- 아릴 및 n- 헤테로아릴우레아 유도체(new n-aryl and n-heteroarylurea derivatives as inhibitors of acyl coenzyme a : cholesterol acyl transferase(acat)

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KR950701621A
KR950701621A KR1019940704262A KR19940704262A KR950701621A KR 950701621 A KR950701621 A KR 950701621A KR 1019940704262 A KR1019940704262 A KR 1019940704262A KR 19940704262 A KR19940704262 A KR 19940704262A KR 950701621 A KR950701621 A KR 950701621A
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methylthio
methylpyridin
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에스. 하마나카 어니스트
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알렌 제이. 스피겔
화이자 인코포레이티드
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Abstract

본 발명의 하기 일반식(Ⅰ)의 화합물, 그의 약학적으로 허용가능한 염에 관한 것이다:
상기식에서 Q, R17, R18및 R1은 상기 정의한 바와 같다. 상기 일반식(Ⅰ)의 화합물은 아실 조효소 A:콜레스테롤 아실전이효소(ACAT)의 억제제이며 이는 고지질형증 및 동맥경화증 칠제로서 유용하다.

Description

아실 조효소 A:콜레스테롤 아실 전이효소(ACAT)의 억제제로서 신규한 N-아릴 및 N-헤테로아릴우레아 유도체(NEW N-ARYL AND N-HETEROARYLUREA DERIVATIVES AS INHIBITORS OF ACYL COENZYME A: CHOLESTEROL ACYL TRANSFERASE(ACAT)
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 하기 일반식(Ⅰ)의 화합물 또는 그의 약학적으로 허용가능한 염:
    상기식에서 Q는 산소 또는 황이고; R17은 -(CH2)n-(CR19R20)Z(CH2)r-Ar (ⅩⅩⅩⅧ)이고, 여기에서, n은 0또는 1내지 3의 정수이고, z는 0또는 1이고, r은 0또는 1내지 4의 정수이고, R19및 R20은 독립적으로 수소, 임의로 할로겐화된(C1-C12)알킬, 임의로 치환된 아릴-(C1-C5)알킬, (C3-C8-)사이클로 알킬-(C1-C5)알킬 및 Ar이거나, 또는 이들이 결합된 탄소원자와 함께 (C4-C7)사이클로알킬 고리 또는 벤젠 융합된 (C5-C7)사이클로알킬 또는 -헤테로알킬 고리를 형성하나, 단 이들이 모두 수소일수는 없고, Ar은 하기 일반식들로 이루어진 그룹들중에서 선택되고;
    상기식들에서, U는 J, 직접결합, -CH=CH- 또는 -CH2CH2-이고, z,n 및 r은 상기 정의한 바와 같고, x는 3내지 10의 정수이고, w는 0또는 1내지 x-1의 정수이고, R21, R22및 각각의 R23은 독립적으로 임의로 할로겐화된 (C1-C6)알킬, 임의로 할로겐화된 (C1-C6)알콕시, 임의로 할로겐화된 (C1-C6)알킬티오, 페닐 및 할로겐으로 이루어진 그룹중에서 선택되고, 이때 상기 알킬, 알콕시 및 알킬티오 그룹의 알킬 그룹들은 직쇄이거나, 또는 3개 이상의 탄소원자를 포함한 경우 분지되거나, 환상이거나 또는 환상과 분지되거나 또는 직쇄인 잔기의 조합일수 있거나, 또는 R21및 R22는 함께 일반식(-J(CH2)t-J- 또는 -(CH2)q-의 그룹을 형성하고, 여기에서 J는 산소 또는 황이고, t는 1내지 3의 정수이고, q는 3내지 5의 정수이고, K는 J- 또는 -CH=CH-이고, L은 -(CH3)u또는 -(CH2)v-J-이고, 여기에서 J는 상기 정의한 바와 같고, u는 3내지 5의 정수이고, v는 2, 3 또는 4이고; R16은 수소, 임의로 치환된 (C1-C6)알킬, 임의로 치환된 (C3-C8)사이클로알킬 또는 임의로 치환된 아릴-(C1-C4)알킬이나, 단 일반식(ⅩⅩⅩⅧ)에서 n, z및 r중 어느 하나가 0이 아닌 경우, R18은 수소이고; R1은 하기 일반식들의 그룹들중에서 선택되거나;
    상기식들에서, m은 0 또는 1내지 4의 정수이고, y는 0또는 1이고, 1은 각각 독립적으로 0내지 3의 각각의 R6및 R15는 독립적으로 할로겐, 임의로 할로겐화된 (C1-C6)알킬, 임의로 할로겐화된 (C1-C6)알콕시, 임의로 할로겐화된 (C1-C6)알킬티오, (C5-C7)사이클로알킬티오, 페닐(C1-C6)알킬티오, 치환된 페닐티오, 페테로아릴티오, 헤테로아릴옥시, (C1-C6)알킬설피닐, (C1-C6)알킬설포닐, (C5-C7)사이클로알킬설피닐, (C5-C7)사이클로알킬설포닐, 페닐(C1-C6)알킬설피닐, 페닐(C1-C6)알킬설포닐, 치환된 페닐설피닐, 치환된 페닐설포닐, 헤테로아릴설피닐, 헤티로아릴설포닐 및 NR10R11(여기에서 R10및 R11은 동일하거나, 상이하며, 수소(C1-C6)알킬, 페닐, 치환된 페닐, (C1-C6)아실, 아로일 및 치환된 아로일로 이루어진 그룹중에서 선택되고, 이때 상기 치환된 페닐 및 치환된 아로일 그룹은 (C1-C6)알킬, (C1-C6)알콕시, (C1-C6)알킬티오, 할로겐 및 트리플루오로메틸로 이루어진 그룹중에서 독립적으로 선택된 하나이상의 치환체로 치환되거나, 또는 R10및 R11은 이들이 결합된 질소와 함께 피레리딘, 피롤리딘 또는 모르폴린 고리를 형성한다)로 이루어진 그룹중에서 선택되고; B, D, E 및 G는 질소 및 탄소로 이루어진 그룹중에서 선택되나, 단, B, D 및 E중의 하나이상이 질소이며, G가 질소인 경우, 그룹(ⅩⅩⅥ)는 피리미딘 고리의 4또는 5번 위치(a 및 b로 표시함)에서 일반식(Ⅰ)의 질소에 결합되고, 이때 상기 임의의 질소들은 산화될 수도 있고; 또는 R1은 일반식
    상기식에서, R7, R8, R9는 동일하거나 상이하며, 각각 독립적으로 임의로 할로겐화된 (C1-C5)알콕시, 임의로 할로겐화된 (C1-C5)알킬티오, 임의로 할로겐화된 (C1-C5)알킬 및 할로겐으로 이루어진 그룹중에서 선택되나; 단 R1이 일반식(ⅩⅩⅡ)의 그룹일때 Ar은 일반식(ⅩⅩⅩⅢ)또는 (ⅩⅩⅩⅤ)의 그룹이고, K는 R19및 R20이 독립적으로 수소및 할로겐화된 (C1-C12)알킬중에서 선택될때(이때, R19또는 R20은 둘다 수소가 아니다)를 제외하곤, CH=CH가 아니고, 일반식(ⅩⅩⅩⅧ)의 r은 0이다.
  2. 제1항에 있어서, R1은 E가 탄소이고, B또는 D가 질소인 일반식(ⅩⅩⅣ)의 그룹인 화합물.
  3. 제1항에 있어서,R1이 G가 탄소인 일반식 (ⅩⅩⅥ)의 그룹인 화합물.
  4. 제1항에 있어서,R1이 G가 탄소인 일반식 (ⅩⅩⅥ)의 그룹인 화합물.
  5. 제2항에 있어서,
    R1이 일반식이고,
    R15가 임의로 치환된 (C1-C8)알킬, 임의로 치환된 (C1-C8)알콕시 및 임의로 치환된 (C1-C8)알킬티오, 바람직하게 알킬티오로 이루어진 그룹중에서 선택되고; R17이 벤젠융합된 (C5-C8)사이클로알킬 및 임의로 치환된 (C1-C8)알킬로 이루어진 그룹중에서 선택되고, 이때 상기 치환체들은 페닐, 벤조[b]티오페닐, 비페닐, 플루오레닐, 나프틸, 할로겐 및 (C3-C12)사이클로알킬로 이루어진 그룹중에서 선택되고, 이때 상기 페닐, 나프틸, 사이클로알킬, 비페닐, 플루오레닐 및 벤조[b] 티오페닐 그룹들은 임의로 할로겐화된 (C1-C6)알킬, 임의로 할로겐화된 (C1-C5)알콕시, 임의로 할로겐화된 (C1-C6)알킬티오 및 할로겐으로 이루어진 그룹중에서 선택된 치환체들로 임의로 치환되고; R18이 수소, 임의로 할로겐화된 (C1-C8)알킬 (C3-C12)사이클로알킬 또는 임의로 치환된 아릴-(C1-C6)알킬중에서 선택되고, 이때 상기 아릴 그룹은 임의로 할로겐화된 (C1-C6)알킬, 임의로 할로겐화된 (C1-C6)알콕시, 임의로 할로겐화된 (C1-C6)알킬티오 및 할로겐으로 이루어진 그룹중에서 선택된 치환체로 임의로 치환된 화합물.
  6. 제3항 또는 제4항에 있어서,
    R1이 일반식
    R6가 각각 독립적으로 (C1-C8)알킬 및 (C1-C8)알킬티오로 이루어진 그룹중에서 선택되고, R17이 벤젠융합된 (C5-C8)사이클로알킬 및 임의로 치환된 (C1-C8)알킬로 이루어진 그룹중에서 선택되고, 이때 상기 치환체들은 페닐, 벤조[b]티오페닐, 비페닐, 플루오레닐, 나프틸, 할로겐 및 (C3-C12)사이클로알킬로 이루어진 그룹중에서 선택되고, 이때 상기 페닐, 나프틸, 사이클로알킬, 비페닐, 플루오레닐 및 벤조[b]티오페닐 그룹들은 임의로 할로겐화된 (C1-C6)알킬, 임의로 할로겐화된 (C1-C6)알콕시, 임의로 할로겐화된 (C1-C6)알킬티오 및 할로겐으로 이루어진 그룹중에서 선택된 치환체들로 임의로 치환되고; R18이 수소, 임의로 할로겐화된 (C1-C8)알킬, (C3-C12)사이클로 알킬 또는 임의로 치환된 아릴-(C1-C6)알킬 중에서 선택되고, 이때 상기 알리그룹은 임의로 할로겐화된(C1-C6)알킬 임의로 할로겐화된 (C1-C6)알콕시, 임의로 할로겐화된 (C1-C6)알킬티오 및 할로겐으로 이루어진 그룹중에서 선택된 치환제로 임의로 치환되나, 단 R1이 일반식(ⅩⅩⅥB)의 그룹인 경우, 2번 위치의 R6은 바람직하게 수소 또는 알킬이고 4번 및 6번 위치의 R6은 각각 바람직하게 알킬티오인 화합물.
  7. 제1항에 있어서, N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(인단-2-일)-N′-(4-이소프로필벤질)우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(2, 5-디메틸벤질)-N′-(인단-2-일)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(2, 4-디메틸벤질)-N′-(인단-2-일)우레아; N-[4,6-비스(메틸티오)-2-메틸피리딘-5-일]-N′-(인단-2-일)-N′-(4-이소프로필벤질)우레아; N-[4,6-비스(메틸티오)-2-메틸피리딘-5-일]-N′-(2, 4-디메틸벤질)-N′-(인단-2-일)우레아; N-(2,5-디메틸벤질)-N-(인단-2-일)-N′-(6-메틸티오퀴놀린-5-일)우레아; N-[2,4-비스(메틸티오)-2-메틸피리딘-5-일]-N′-(2, 5-디메틸벤질)-N′-(인단-2-일)우레아; N-[4,6-비스(메틸티오)-2-메틸피리딘-5-일]-N′-(2-일)-N′-[4-(3-메틸부틸)벤질]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(인단-2-일)-[4-(3-메틸부틸)벤질]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(인단-1-일)-N′-(나프트-1-일메틸)우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(인단-1-일)-N′-(나프트-2-일메틸)우레아; N-[2, 4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(인단-1-일)-N′-(4-t-부틸벤질)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(인단-2-일)-N′-(나프트-1-일메틸)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(인단-2-일)-N′-(나프트-2-일메틸)우레아; N-[2,4-비스(메틸티오-메틸피리딘-3-일]-N′-(인단-2-일)-N′-(2,4,6-트리메틸벤질)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-(2,3-디클로로벤질)-N′-(인단-2-일)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2,2-디페닐에틸]우레아; N-(2,2-디페닐에틸)-N′-(6-메틸티오퀴놀린-5-일]-N′-(2,2-디페닐에틸)우레아; N-[4,6-비스(메틸티오)피리미딘-5-일]-N′-(2,2-디페닐에틸)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(1-페닐사이클로펜틸)메틸]우레아; N-[6-메틸티오퀴놀린-5-일]-N′-[(1-페닐사이클로펜틸)메틸]우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(1-(4-메틸페닐)사이클로펜틸)메틸]우레아; N-[(1-(4-메틸페닐)사이클로펜틸)메틸]-N′-(6-메틸티오퀴놀린-5-일)우레아; N-(6-메틸티오퀴놀린-5-일)-N′-[(1-페닐사이클로헥실)메틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(1-페닐사이클로헥실)메틸]우레아; N-[(1-(4-메틸페닐)사이클로헥실)메틸]-N′-(6-메틸티오퀴놀린-5-일]우레아; N-[4,6-비스(메틸티오)-2-메틸피리미딘-5-일]-N′-[(1-(4-메틸페닐)사이클로헥실]메틸]우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(1-(4-메틸페닐)사이클로헥실)메틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-에틸-2-페닐)부틸]우레아; N-[2,4-비스(이소프로필티오)-6-메틸피리딘-3-일]-N′-[(2-에틸-2-페닐)부틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-에틸-2-{2-메틸페닐)부틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-페닐-2-프로필)펜틸]우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-{2-메틸페닐}-2-프로필)펜틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-{2-메틸페닐}-2-부틸)헥실]우레아; N-[2, 4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-{2, 5-디메톡시페닐}-2-프로필)펜틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-{2,3-디메틸페닐}-2-프로필)펜틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-{2,5-디메틸페닐}-2-프로필)펜틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-(2-메틸페닐)헥실]우레아; N-[(2-(2-메틸페닐)헥실]-N′-[6-메틸티오퀴놀린-5-일]-우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-(4-메틸페닐)헵틸]우레아; N-[2-(4-메틸페닐)헵틸]-N′-(6-메틸티오퀴놀린-5-일)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-3-메틸페닐)헵틸]우레아; N-[2-(3-메틸페닐)헵틸]-N′-(6-메틸티오퀴논린-5-일)우레아; N-[2-(3-메틸페닐)헵틸]-N′-(6-메틸시퀴놀린-5-일)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-(2,5-디메틸페닐)헥실]우레아; N-[2-(2,5-디메-틸페닐)헥실]-N′-(6-메틸티오퀴놀린-5-일]우레아; N-[2-(2,5-디메틸페닐)헥실]-N′-(6-메틸티오퀴놀린-5-일]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-(2,5-디메틸페닐)헵틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-(2, 4-디메틸페닐)헥실]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-(3-메틸페닐)헥실]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(2, 4-디메틸페닐)헵틸]우레아; N-(2, 4-비스(메틸리오)-6-메틸피리딘-3-일]-N′-[2-(나프트-1-일)헵틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(나프트-2-일)헥실]우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(나프트-1-일)헥실]우레아;N-(6-메틸티오퀴놀린-5-일)-N′-[2-(나프트-1-일)헥실]우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(2,3-디메틸시페닐)헵틸]우레아; N-[2-(2,3-디메톡시페닐)헵틸]-N′-(6-메틸티오퀴놀린-5-일)우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(3-메틸페닐)옥틸]우레아; N-[2-(3-메틸페닐)옥틸]-N′-(6-메톡시퀴놀린-5-일)우레아; N-[2-(3-메틸페닐)옥틸]-N′-(6-메톡시퀴놀린-5-일)우레아;N-[2-(나프트-1-일)헵틸]-N′-(6-메톡시퀴놀린-5-일)우레아; N-[2-(나프트-1-일)헵틸]-N′-(6-메톡시퀴놀린-5-일)우레아; N-[2-(2,4-디메틸페닐)헵틸]-N′-(6-메틸티오퀴놀린-5-일)우레아; N-[2-(2,4-디메틸페닐)헵틸]-N′-(6-메톡시퀴놀린-5-일)우레아; N-[2,4-비스(메틸)-6-메틸피리딘-3-일]-N′-[2-(3,4,5-트리메털시페닐)헵틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(2,5-디메틸-4-메톡시페닐)헵틸]우레아; N-[2-(2,5-디메톡시페닐)헵틸]-N′-[6-메틸티오퀴놀린-5-일)우레아; N-[2-(2,5-디메톡시페닐)헵틸]-N′-[6-메틸시퀴놀린-5-일)우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(3,5-디메톡시페닐)헵틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(2, 5-디메틸페닐)옥틸]우레아; N-[2, 4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-2[2-(3-메틸페닐)-6,6,6-트리플루오로헥실]우레아; N-[2-(3-메틸페닐)헵틸]-N′-(6-펜틸티오퀴놀린-5-일)우레아;N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-{2-(5-클로로벤조[b]티오펜-3-일)헵틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(3,5-디메틸페닐)헵틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2-(2,5-디메틸페닐)옥틸]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[5-메틸-2-{3-메틸페닐}헥실]우레아; N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[(2-(2,5-디메티리페닐)-4-페닐펜틸]우레아; 및 N-[2,4-비스(메틸티오)-6-메틸피리딘-3-일]-N′-[2,(2,5-디메티리페닐)-5-페닐펜틸]우레아로 이루어진 그룹중에서 선택된 화합물.
  8. 제1항에 있어서, 트리튬 및 탄소-14로 이루어진 그룹중에서 선택된 하나이상의 방사성 표지를 포함하는 화합물.
  9. ACAT억제 유효량의 제1항의 화합물 및 약학적으로 허용가능한 희석제 또는 담체를 포함하는 약학 조성물.
  10. ACAT억제량의 제1항의 화합물을 인간 또는 동물에게 투여함을 포함하는, 상기 인간 또는 동물의 ACAT억제 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019940704262A 1992-05-28 1993-04-20 아실 조효소a : 콜레스테롤 아실 전이효소(acat)의 억제제로서 신규한 n- 아릴 및 n- 헤테로아릴우레아 유도체(new n-aryl and n-heteroarylurea derivatives as inhibitors of acyl coenzyme a : cholesterol acyl transferase(acat) KR950701621A (ko)

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US89005092A 1992-05-28 1992-05-28
US07/890,050 1992-05-28
PCT/US1993/003539 WO1993024458A1 (en) 1992-05-28 1993-04-20 New n-aryl and n-heteroarylurea derivatives as inhibitors of acyl coenzyme a:cholesterol acyl transferase (acat)

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CA2134359A1 (en) 1993-12-09
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EP0642498A1 (en) 1995-03-15
IS4023A (is) 1993-11-29
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OA10114A (en) 1996-12-18
SK142694A3 (en) 1995-06-07
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HRP930931A2 (en) 1997-06-30
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HU9301552D0 (en) 1993-09-28
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BG99188A (bg) 1995-07-28
BR9306421A (pt) 1998-09-15
FI932423A0 (fi) 1993-05-27
RU94046149A (ru) 1996-11-27
YU37193A (sh) 1997-07-31
HUT64303A (en) 1993-12-28
US6001860A (en) 1999-12-14
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AU4028393A (en) 1993-12-30

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