KR840006215A - 벤즈이미다졸 유도체의 제조방법 - Google Patents

벤즈이미다졸 유도체의 제조방법 Download PDF

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KR840006215A
KR840006215A KR1019830004492A KR830004492A KR840006215A KR 840006215 A KR840006215 A KR 840006215A KR 1019830004492 A KR1019830004492 A KR 1019830004492A KR 830004492 A KR830004492 A KR 830004492A KR 840006215 A KR840006215 A KR 840006215A
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알프레드 스피쳐 웨인
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아더 알. 웨일
일라이 릴리앤드 캄파니
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Abstract

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Description

벤즈이미다졸 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (15)

  1. (A) 일반식(Ⅱ)의 벤즈이미다졸 화합물을 일반식 R1X의 화합물로 알킬화시켜 R2가 하이드록시 또는 아미노가 아닌 일반식(Ⅰ)화합물을 생성시키거나; (B) 일반식(Ⅴ) 화합물을 바람직하게는 무기산의 존재하에 포름산 또는 락트산과 가열하여 R2가 수소 또는 1-하이드록시에틸인 일반식(Ⅰ) 화합물을 생성시키거나; (C) 일반식(Ⅴ)화합물을 시아노겐 할라이드로 페환시켜 R2가 아미노인 일반식(Ⅰ)화합물을 생성시키거나; (D) 일반식 (IB)의 벤즈이미다졸 화합물을 C1-C4알킬할라이드로 알킬화시켜 R2가 C1-C4알킬아미노인 일반식(Ⅰ)화합물을 생성시키거나; (E) 일반식(IC)의 벤즈이미다졸 화합물을 약염 기존재하에 메틸할라이드로 알킬화시켜 R2가 메틸메르갚토인 일반식(Ⅰ) 화합물을 생성시키거나; (F) 일반식(IB)의 벤즈이미다졸 화합물을 C2-C4무수물, 무수 포름산 및 무수 아세트산의 혼합무수물 또는 C1-C4아실할라이드로 아실화시켜 R2가 C1-C4아실아미노인 일반식(Ⅰ) 화합물을 생성시키거나; (G) 일반식 (Ⅱ)의 벤즈이미다졸 화합물을 R4R5NH및 포름알데하이드와 반응시켜 R1이 R4R5NCH2-인 일반식(Ⅰ)화합물을 생성시키거나; (H) 일반식 (Ⅴ)화합물을 일반식(Ⅶ)의 β-케토에스테르와 축합시켜 R2가 수소이고, R1이 C5-C7사이클로알켄-1-일인 화합물을 생성시키거나; (I) 일반식 (ID)의 벤즈이미다졸 화합물을 무수물 또는 아실할라이드로 에스테르화시켜 R3가 C2-C8알카노일옥시, 비치환된 또는 치환된 페페아세톡시, 또는 비치환된 또는 치환된 벤조일옥시인 일반식(Ⅰ)화합물을 생성시키거나; (J) 일반식(IA)의 벤즈이미다졸 화합물을 하이드록실아민, 또는 그의 염산염, 히드라진 또는 C1-C4알콕시아민과 반응시켜 Z가 하이드록시이미노, 히드라조노 또는 C1-C4알콕시이미노인 일반식(Ⅰ)화합물을 생성시키거나; (K)Z가 하이드록시아미노인 일반식(Ⅰ)화합물을 C1-C4무수물 또는 C1-C4아실할라이드로 아실화시켜 Z가 C1-C4아실옥시이미노인 일반식(Ⅰ)화합물을 생성시키거나; (L) Z가 하이드록시이미노인 일반식(Ⅰ)화합물을 C1-C4알킬할라이드로 에테르화시키거나 R3가인 일반식(Ⅰ)화합물을 C1-C4알콕시아민으로 알킬화시켜 Z가 C1-C4알콕시이미노인 일반식(Ⅰ)화합물을 생성시키거나; (M) 일반식(IF)의 벤즈이미다졸 화합물을 산으로 탈수시켜 Z가 C1-C7알킬리덴, =CHCN,=CHCONH2, 또는 =CHCO2(C1-C4알킬)인 일반식(Ⅰ)화합물을 생성시키거나; (N) 일반식(IGC)의 벤즈이미다졸 화합물을 할로겐하제와 반응시켜 Z가 =CHBr, =CHCl, =CBr2, =CCl2또는 =CBrCl인 일반식(Ⅰ) 화합물을 생성시키거나; (O) 일반식(Ⅰ)의 벤즈이미다졸 화합물을 그의 5 및 6이성체로 분리시키거나; (P) Z가 하이드록시이미노, C1-C4알콕시이미노, C1-C4아실옥시이미노 또는 히드라조노인 일반식(Ⅰ)의 벤즈이미다졸 화합물을 그의 산 및 안티 이성체로 분리시키거나; (Q) Z가 C1-C7알킬리덴, =CHBr, =CHCl, =CBr2, =CCl2, =CBrCl, =CHCN, =CHCONH2또는 =CHCO2(C1-C4알킬)인 일반식(Ⅰ)의 벤즈이미다졸 화합물을 그의 시스 또는 트란스 이성체로 분리시키거나; (R) 일반식(Ⅰ)화합물을 염화하여 약학적으로 무독한 염을 생성시킴을 특징으로 하여 일반식(Ⅰ)의 벤즈이미다졸 화합물 및 그의 약학적으로 무독한염을 제조하는 방법.
  4. 상기식에서, R1은 C1-C8알킬, C2-C8알케닐, C3-C7사이클로알킬, C5-C7사이클로알켄-1-일, 2-피리딜, 티아졸릴, 아다만틸, 하이드록시-치환된 C1-C8알킬, 비치환된 또는 치환된 페닐, 비치환된 또는 치환된 벤질 또는 R4R5NCH2-(여기에서 R4및 R5는 독립적으로 C1-C3알킬이거나 R4및 R5가 부착된 질소원자와 함께 피롤리다노, 피페리디노 또는 모르폴리노이다)이며; R2는 수소, 아미노, C1-C4알킬아미노,메틸메르캅토, 하이드록시, C1-C4아실아미노 또는 1-하이드록시에틸이고 (단, 일반식(Ⅱ) 에서는 R2가 하이드록시 또는 아니노가 아니며 일반식(ID)에서는 하이드록시 그룹이 아님); R3는 C2-C8알카일옥시, 비치환된 또는 치환된 페닐 아세톡시,비치환된 또는 치환된 베조일옥시 또는(여기에서 Z는 산소, 하이드록시이미노, C1-C4알콕시이미노, C1-C4아실옥시이미노, 히드라조노, C1-C7알킬리덴, =CHBr, =CHCl, =CBr2, =CCl2, =CBrCl, =CHCN, =CHCONH2또는 =CHCO2(C1-C4알킬)이며, R6는 C1-C7알킬, C3-C7사이클로알킬, (C3-C7사이클로알킬) 메틸, 2-(C5-C7사이클로알킬)에틸, 비치환된 또는 치환된 벤질, 비치환된 또는 치환된 페닐이다)이며; R3는 5 또는 6위치에 있고 단, R2가 하이드록시인 경우에 R1은 단지 C5-C71-사이클로알케닐일수 있으며; X는 플루오로, 클로로, 브로모 또는 요도이고 n은 0내지 2이며, R7및 R8중의 하나는 수소이고, 다른 하나는 수소, C1-C6알킬, -CN, -CONH2, 또는 -CO2-(C1-C4알킬)을 나타낸다.
  5. 제1항의 (J)에 있어서, 1-(t-부틸)-6-벤조일벤즈이미다졸을 하이드록실아민 염산염과 반응시켜 1-(t-부틸)-6-(α-하이드록시이미노벤질)벤즈이미다졸을 제조하는 방법.
  6. 제1항의(J)에 있어서, 1-사이클로헥실-2-아미노-6-벤조일벤즈이미다졸을 하이드록실아민 염산염과 반응시켜 1-사이클로헤실-2-아미노6-(α-하이드록시이미노벤질)-벤즈이미다졸을 제조하는방법.
  7. 제1항의(J)에 있어서, 1-사이클로헥실-2-아미노-6-(4'-메톡시벤조일)벤즈이미다졸을 하이드록실아민 염산염과 반응시켜 1-사이클로헥실-2-아미노-6-(α-하이드록시이미노-4'-메톡시벤질)벤즈이미다졸을 제조하는 방법.
  8. 제1항의(J)에 있어서, 1-이소프로필-2-아미노-6-벤조일벤즈이미다졸을 하이드록실아민 염사염과 반응시켜 1-이소프로필-2-아미노-6-(α-하이드록시이미노벤질) 벤즈이미다졸을 제조하는 방법.
  9. 제1항의(J)에 있어서, 1-페닐-2-아미노-6-벤조일벤즈이미다졸을 하이드록실아민 염산염과 반응시켜 1-페닐-2-아미노-6-(α-하이드록시이미노벤질)벤즈이미다졸을 제조하는 방법.
  10. 제1항의(M)에 있어서, 1-이소프로필-2-아미노-6-(α-하이드록시-α-에틸벤질)벤즈이미다졸을 포름산과 반응시켜 1-이소프로필-2-아미노-6-(1-페닐-1-프로페닐)벤즈이미다졸을 제조하는 방법.
  11. 제1항의(N)에 있어서, 1-이소프로필-2-아미노-6-(1-페닐에테닐)벤즈이미다졸을 N-브로모숙신이미드와 반응시켜 1-이소프로필-2-아미노-6-(1-페닐-1-브로모에테닐)벤즈이미다졸을 제조하는 방법.
  12. 제1항의(M)에 있어서, 1-이소프로필-2-아미노-6-(α-하이드록시-α-시아노메틸벤질)벤즈이미다졸을 포름산과 반응시켜 1-이소프로필-2-아미노-6-(1-페닐-2-시아노에틸닐)벤즈이미다졸을 제조하는 방법.
  13. 제1항의(M)에 있어서, 1-페닐-2-아미노-6-(α-하이드록시-α-시아노메틸벤질)벤즈이미다졸을 포름산과 반응시켜 1-페닐-2-아미노-6-(1-페닐-2-시아노에틸닐)벤즈이미다졸을 제조하는 방법.
  14. 제1항의(M)에 있어서, 1-이소프로필-2-아미노-6-[α-하이드록시-α-비스(트리메틸실릴)아세트아미도]-벤질벤즈이미다졸을 염화 암모늄과 반응시켜 3-(1-이소프로필-2-아미노벤즈이미다졸-6-일)-3-페닐-2-프로펜아미드를 제조하는 방법.
  15. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019830004492A 1982-09-27 1983-09-26 벤즈이미다졸 유도체의 제조방법 KR840006215A (ko)

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GB8325360D0 (en) 1983-10-26
PT77398B (en) 1986-03-20
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AU1956683A (en) 1984-04-05
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FI833424A0 (fi) 1983-09-23
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US4492708A (en) 1985-01-08
EP0111993A3 (en) 1984-07-25

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