KR830007591A - 2-히드록시-4-(치환) 페닐 시클로알칸류와 이들의 유도체 및 그 중간 생성물의 제조방법 - Google Patents

2-히드록시-4-(치환) 페닐 시클로알칸류와 이들의 유도체 및 그 중간 생성물의 제조방법 Download PDF

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KR830007591A
KR830007591A KR1019810003501A KR810003501A KR830007591A KR 830007591 A KR830007591 A KR 830007591A KR 1019810003501 A KR1019810003501 A KR 1019810003501A KR 810003501 A KR810003501 A KR 810003501A KR 830007591 A KR830007591 A KR 830007591A
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로스 존슨 미가엘
제이알 로렌스 쉐르만 멜빈
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윌리암 데이비스 헌
화이자 인코포레이티드
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Abstract

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Description

2-히드록시-4-(치환) 페닐 시클로알칸류와 이들의 유도체 및 그 중간생성물의 제조방법
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Claims (6)

  1. 하기 일반식(I)을 가진 화합물을 제조함에 있어서
    (상기 일반식에서,
    R은 수소, 수산기, 1-5개의 탄소원자를 가진 알카노일옥시, 아미노 또는 아세트아미도이고,
    R1은 수소, 벤질 또는 1-5개의 탄소원자를 가진 알카노일이며,
    S는 1 또는 2의 정수이고,
    Y는 -CH(R3)CH2- 또는 -CH(R2″)CH(R2)- 이며,
    R2는 수산기 또는 1-6개의 탄소원자를 가진 X-치환 알킬기이고,
    R2″는 수소 도는 메틸기이며,
    R3는 수소, 시아노 또는 1-3개의 탄소원자를 가진 X-치환 알킬기이고.
    X는 -OR6, -NR6R7, -COOR7, -CONR7R8또는 옥소이고,
    R6는 수소ㅡ 1-6개의 탄소원자를 가진 알킬 또는 아세틸기이며,
    R7과 R8는 각각 수소 또는 1-6개의 탄소원자를 가진 알킬기이고,
    X가 -NR6R7, -COOR7또는 -CORN7R8일때 이것은 R2또는 R3중의 말단 탄소원자에 위치하게 되며,
    R6가 아세틸기일때 R7은 수소이고,
    W는 수수, 피리딜 또는인데, 여기서 W1은 수소, 염소 또는 불소이며,
    W가 수소일 때 Z는
    (a) 5-13개의 탄소원자를 가진 알키렌 또는
    (b) -(alk1)m-O-(alk2)n-이고, 여기서 (alk1) 및 (alk2)은 각각 1-13개의 탄소원자를 가진 알키렌이고, m과 n은 각각 0또는 1이고, (alk1) 과 (alk2)내의탄소원자의 합이 5개보다는 적지않고 13개 보다는 크지 않으며, m과 n 중의 최소한 하나가 1인 조건을 가지며,
    W가 수소 이외의 것일때 Z는
    (a) 3-8개의 탄소원자를 가진 알키렌이거나
    (b) -(alk1)m-O-(alk2)n-이고, 여기서 (alk1)과 (alk2)는 각각 1-8개의 탄소원자를 가진 알키렌이고, m과 n은 각각 0 또는 1이며, (alk1)과 (alk2)내의 탄소원자의 합이 3개 보다는 적지 않고 8개 보다는 크지 않고 m과 n중의 최소한 하나가 1인 조건을 가짐),
    하기 일반식(Ⅱ)를 가진 화합물을 환원시키고,
    (상기 일반식에서, R, Y, S, Z 및 W는 위에서 정의한 바와 같음),
    필요에 따라서 환원전 또는 환원후에,
    (a) R2또는 R3가 알케닐기인 일반식 I 또는 Ⅱ의 화합물을 수화시키는 단계.
    (b) R2또는 R3가 알케닐기인 일반식 I 또는 Ⅱ의 화합물을 산화시키는 단계.
    (c) R2또는 R3가 옥소알킬기인 일반식 I 의 화합물을 비티히 반응을 시키는 단계.
    (d) 일반식 Ⅱ의 화합물을 케탈화시키는 단계.
    (e) 일반식 Ⅱ의 케탈 유도체를 비티히 반응을 시키는 단계.
    (f) R1이 수소이고 또는 R가 아미노기인 일반식 I 또는 Ⅱ의 화합물을 아실화시키는 단계.
    (g) R1이 벤질기인 일반식 I 또는 Ⅱ의 화합물을 탈블록화시키는 단계
    (h) R2또는 R3가 히드록시 알킬기이고 R1이 벤질기인 일반식 I 또는 Ⅱ의 화합물을 알칼화시커서 R2또는 R3가 알콕시 알킬기일 일반식 I 또는 Ⅱ의 화합물을 제조하는 단계
    (i) X가 -NR6R7인 일반식 I 또는 Ⅱ의 화합물중에 약리학적으로 허용되는 산부가염을 제조하는 단계들 중에서 하나 또는 그 이상의 단계를 포함하는 것을 특징인 제조방법.
  2. 하기 일반식(Ⅲ)을 가진 화합물을 제조함에 있어서
    (상기 일반식에서,
    S는 1 또는 2이고,
    W는 수소, 피리딜 또는이며, 여기서
    W1는 수소, 염소 또는 불소이고,
    W가 수소일때 Z는
    (a) 7-11개의 탄소원자를 가진 알키렌이거나,
    (b) -(alk1)m-O-(alk2)n-이며, 여기서 (alk1)과 (alk2)는 각각 1-11개의 탄소원자를 가진 알키렌이고, m과 n는 각각 0 또는 1이며, (alk1)과 (alk2)내의 탄소원자의 합이 7개 보다는 적지 않고 11개 보다는 크지 않으며 최소한 m과 n중의 하나가 1인 조건을 가지며,
    W가 수소 이외의 것일때 Z는
    (a) 4-7개의 탄소원자를 가진 알키렌이거나,
    (b) -(alk1)m-O-(alk2)n-이며, 여기서 (alk1)과 (alk2)는 각각 1-7개의 탄소원자를 가지는 알키렌이고, m과 n은 0 또는 1이고, (alk1)과 (alk2)내의 탄소원자의 합이 4개보다는 적지 않고 7개보다는 크지 않으며 최소한 m과 n 중의 하나가 1인 조건을 가짐).
    하기 일반식(Ⅳ)를 가진 화합물을 시안화나트륨 또는 칼륨으로써 반응시키고
    필요에 따라서
    (a) 일반식 Ⅲ의 화합물의 옥소기를 환원시커서 해당하는 수산화물을 제조하는 단계
    (b) 일반식 Ⅲ의 화합물 중에 CN기를 디이소부틸알루미늄 수소화물로써 반응시커서 포르밀로 전환시키는 단계
    (c) 단계 (b)에서 제조한 포르밀 유도체로부터 해당하는 히드록시메틸 유도체를 얻기 위해서 환원시키는 단계들 중에서 한단계 또는 그 이상의 단계들을 포함하는 것을 특징인 제조방법.
  3. R2또는 R3가 알케닐기일때 전기화합물을 붕수소화-산화에 의해서 수화시키는 것이 특징인 특허청구의 범위 제1항 기재의 방법
  4. 하기 일반식(Ⅱ-A)을 가진 화합물을 제조함에 있어서
    (상기 일반식에서,
    S, R1, Z 및 W는 특허청구의 범위 제1항에서 정의한 바와 같으며,
    Y′는 -CH(R2″)CH(R2°)- 또는 -CH(R3°)CH2-이며,
    여기서 R2″는 수소 또는 메틸기이고 R2°와 R3°는 각각 히드록시 알킬기임).
    하기 일반식(Ⅱ-B)을 가진 화합물을 수화시키는 것을 특징인 제조방법.
    상기 일반식에서,
    S, R1, Z 및 W는 위에서 정의한 바와 같으며,
    Y″는 -CH(R2″)CH(R2°)- 또는 -CH(R3°)CH2-이고,
    여기서 R2″는 위에서 정의한 바와 같으며, R2°와 R3°는 각각 알케닐기임).
  5. 하기 일반식(Ⅱ′)을 가진 화합물을 제조함에 있어서
    상기 일반식에서,
    S, R1, Z 및 W는 특허청구의 범위 제1항에서 정의한 바와 같으며,
    Y′는 -CH(R2″)CH(R2°)- 또는 -CH(R3°)CH2-이고,
    여기서 R2″는 수소 또는 메틸기이고, R2°와 R3°는 각각 옥소알킬기임)
    하기 일반식(Ⅱ′)의 화합물을 산화시키는 것이 특징인 제조방법.
    (상기 식에서,
    S, R1, Z 및 W는 위에서 정의한 바와 같으며,
    Y′는 -CH(R2″)CH(R2°)- 또는 -CH(R3°)CH2-이고,
    여기서 R2″는 위에서 정의한 바와 같으며, R2″와 R3°는 각각 알케닐기임).
  6. 하기 일반식(Ⅱ-C)를 가진 화합물을 제조함에 있어서,
    (상기 일반식에서,
    S, R1, Z 및 W는 특허청구의 범위 제1항에서 정의한 바와 같으며,
    Y는 -CH-CH(OH)- 또는 -CH(OH)-CH2-임).
    하기 일반식(Ⅱ-D)를 가진 화합물을 산화시커서 해당하는 에폭시드를 제조한 다음 리튬 알루미늄 수소화물로써 전기 에폭시드를 환원시키는 것이 특징인 제조방법.
    (상기 일반식에서,
    S, R1, Z 및 W는 위에서 정의한 바와 같음).
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019810003501A 1980-09-19 1981-09-18 2-히드록시-4-(치환)페닐시클로알칸류와 그 유도체 및 중간체의 제조 방법 KR860000299B1 (ko)

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