KR870010045A - 4h-1-벤조피란-4-온 유도체 및 이의 제조방법 - Google Patents

4h-1-벤조피란-4-온 유도체 및 이의 제조방법 Download PDF

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KR870010045A
KR870010045A KR870003427A KR870003427A KR870010045A KR 870010045 A KR870010045 A KR 870010045A KR 870003427 A KR870003427 A KR 870003427A KR 870003427 A KR870003427 A KR 870003427A KR 870010045 A KR870010045 A KR 870010045A
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락스미나라얀 카티지 삼바
가나파티 나이크 람찬드라
타브 다우드브하이 라크 다왈라 아프
세인 노만하이 도하드왈라 알리후
헬무트 루프 리차드
존 데 소오자 노엘
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하인리히 벡커, 베른하르트 베크
훽스트 아크티엔게젤샤프트
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    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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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    • C—CHEMISTRY; METALLURGY
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    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings

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Abstract

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Description

4H-1-벤조피란-4-온 유도체 및 이의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
제1도는 본 발명에 따르는 일반식(Ⅰ)의 화합물을 제조하는 방법을 개괄적으로 도시한 것이다.
제2도는 제1도에 따른 방법중에서 본 발명에 따르는 바람직한 화합물중 하나를 제조하는 방법으로 도시한 예이다.

Claims (12)

  1. 하기 일반식(Ⅰ)의 화합물 및 이의 약물학적으로 허용되는 산 부가염 및 광학적 이성체.
    상기식에서,
    R1은 수소, 비치환되거나 치환된 C1-C6-알킬, 아릴-C1-C4-알킬, C3-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C4-알킬, C2-C6-알케닐, C3-C6-알키닐, 아릴, 카복실 또는 알데히드 또는 -COO-C1-C4-알킬 그룹이고,
    R2는 수소, C1-C6-알킬, 니트로, 아미노, 디-C1-C4-알킬아미노 또는 디-C1-C4-알킬아미노메틸 또는 할로겐원자이며,
    R3는 C1-C4-알킬, 치환된 C1-C4-알킬, 하이드록실, C1-C4-알콕시, 아릴-C1-C4-알킬, 니트로, 할로겐, 아미노 C1-C4-알킬아미노 또는 디-C1-C4-알킬아미노이고,
    R4는 수소, 하이드록실, C1-C4-알콕시, C1-C4-알카노일옥시, C1-C4-알콕시카보닐, 아릴옥시, 아미노, C1-C4-알킬아미노 또는 디-(C1-C4-알킬)-아미노이며,
    R5는 수소, C1-C6-알킬, 치환된 C1-C6-알킬, 아릴-C|1-C4-알킬, C3-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C4-알킬, -C1-C4-알카노일 또는 아로일이고,
    m은 0 내지 3의 정수이며,
    n은 0 내지 2의 정수이고,
    단, 상기 식에서 세라미 화합물 5,7-디하이드록시-2-메틸-8-[4'-(3'하이드록시-1'-메틸)-피페리디닐]-4H-1-벤조피란-4온은 제외된다.
  2. 제1항에 있어서, R1,R2및 R5가 상기에서 정의된 바와 같고, R3및 R4가 하이드록실 그룹이며, m이 2이고 n이 1인 화합물.
  3. 제1항에 있어서, R1이 수소 또는 C1-C3-알킬이고, R2가 수소 또는 C1-C3-알킬이며, R3및 R4가 각각 하이드록실 그룹이고, R5가 C1-C3-알킬 또는 C3-C5-사이클로알킬이며, m 이 2이고 n이 1인 화합물.
  4. 시스-(±)-2-(2-클로로페닐)-5,7-디하이드록시-8-[4'-(3'-하이드록시-1'-메틸)-페레리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산 부가염.
  5. 시스-(-)-2-(2-클로로페닐)-5,7-디하이드록시-8-[4'-(3'-하이드록시-1'-메틸)-페레리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산 부가염.
  6. 시스-(-)-2-페닐-5,7-디하이드록시-8-[4'-(3'-하이드록시-1'-메틸)-페레리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산 부가염.
  7. 시스-(±)-2-페닐-5,7-디하이드록시-8-[4'-(3'-하이드록시-1'-메틸)-페레리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산 부가염.
  8. 시스-(±)-2-(P-를루오로페닐)-5,7-디하이드록시-8-[4'-(3'-하이드록시-1'-메틸)-페레리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산 부가염.
  9. 시스-(±)-2-(2-피리딜)-8-[4'-(3'-하이드록시-1'-메틸)-페레리디닐]-4H-1-벤조피란-4-온 및 이의 약물학적으로 허용되는 산 부가염.
  10. 일반식(ⅩⅡ)의 화합물을 알칼리 금속 또는 알킬리금속 수소화물 및 일반식 R1-COO-알킬의 산의 알킬 에스테르와 반응시켜 일반식(ⅩⅢ)의 디케톤을 수득하고, 생성된 화합물을 무기산과 반응시킴으로써 폐환시켜 R4가 하이드록실 그룹이고 R2가 수소인 일반식(Ⅰ)의 화합물을 수득하거나, 경우에 따라, R5가 CH3인 일반식(Ⅰ)의 화합물을 하이드록실 그룹을 보호시킨 후에, 브롬화시아노겐과 반응시키고, 생성된 화합물을 산성 또는 알칼리성 조건하에서 반응시켜 R5가 수소인 일반식(Ⅰ)의 화합물을 수득하거나, 경우에 따라, R5가 수소인 일반식(Ⅰ)의 화합물을 할라이드, 산 클로라이드, 토실레이트 및 에논과 같은 적합한 친천자성 시약과 반응시켜 R5가 비치환되거나 치환된 C1-C6-알킬, 아릴-C1-C4-알킬, C3-C|6-사이클로알킬 또는 C3-C6-사이클로알킬-C1-C4-알킬인 일반식(Ⅰ)의 화합물을 수득하거나, 경우에 따라, R2가 수소인 일반식(Ⅰ)의 화합물을 2급 아민 하이드로클로라이드 및 파라포름알데히드와 반응시켜 R2가 디알킬아미노 메틸인 일반식(Ⅰ)의 화합물을 수득하거나, 또는, 경우에 따라, R2가 수소인 일반식(Ⅰ)의 화합물을 니트로화시켜 R2가 NO2인 일반식(Ⅰ)의 화합물을 수득하거나, 경우에 따라, R2가 NO2인 일반식(Ⅰ)의 화합물을 수소화시켜 R2가 아미노그룹인 일반식(Ⅰ)의 화합물을 수득함을 특징으로 하여, 일반식(Ⅰ)의 화합물 및 이의 약물학적으로 허용되는 산 부가염 및 광학적 이성체를 제조하는 방법.
    상기식에서,
    R1은 수소, 비치환되거나 치환된 C1-C6-알킬, 아릴-C1-C4-알킬, C3-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C4-알킬, C2-C6-알케닐, C3-C6-알키닐, 아릴, 카복실 또는 알데히드 또는 -COO-C1-C4-알킬 그룹이고,
    R2는 수소, C1-C6-알킬, 니트로, 아미노, 디-C1-C4-알킬아미노 또는 디-C1-C4-알킬아미노메틸 또는 할로겐원자이며,
    R3는 C1-C4-알킬, 치환된 C1-C4-알킬, 하이드록실, C1-C4-알콕시, 아릴-C1-C4-알킬, 니트로, 할로겐, 아미노, C1-C4-알킬아미노 또는 디-C1-C4-알킬아미노이고,
    R4는 수소, 하이드록실, C1-C4-알콕시, C1-C4-알카노일옥시, C1-C4-알콕시카보닐, 아릴옥시, 아미노, C1-C4-알킬아미노 또는 디-(C1-C4-알킬)-아미노이며,
    R5는 수소, C1-C6-알킬, 치환된 C1-C6-알킬, 아릴-C|1-C4-알킬, C3-C6-사이클로알킬, C3-C6-사이클로알킬-C1-C4-알킬, C1-C4-알카노일 또는 아로일이고,
    m은 0 내지 3의 정수이며,
    n은 0 내지 2의 정수이다.
  11. 제1항에서 청구된 일반식(Ⅰ)의 화합물 또는 이의 약물학적으로 허용되는 산 부가염을 함유하는 약제.
  12. 소염 및 또는 면역조절 작용을 갖는 약제를 제조하는데 있어서의 제1항에서 청구된 화합물의 용도.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR87003427A 1986-04-11 1987-04-10 Process for preparing 4h-1-benzopyran-4-one derivatives KR950009861B1 (en)

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DE19863612337 DE3612337A1 (de) 1986-04-11 1986-04-11 4h-1-benzopyran-4-on-derivate, ein verfahren zu ihrer herstellung und ihre verwendung als arzneimittel
DEP3612337.4 1986-04-11

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KR950009861B1 (en) 1995-08-29
PT84654A (de) 1987-05-01
ATE95519T1 (de) 1993-10-15
IE870941L (en) 1987-10-11
EP0241003B1 (de) 1993-10-06
HK1006021A1 (en) 1999-02-05
AU7139787A (en) 1987-10-15
ATA260587A (de) 1989-07-15
JPH0686446B2 (ja) 1994-11-02
PT84654B (pt) 1989-12-29
AU602891B2 (en) 1990-11-01
IL82149A0 (en) 1987-10-30
ZA872555B (en) 1987-11-25
CA1332238C (en) 1994-10-04
IN164232B (ko) 1989-02-04
IE62244B1 (en) 1995-01-11
DE3612337A1 (de) 1987-10-15
ES2060582T3 (es) 1994-12-01
US4900727A (en) 1990-02-13
DK185287A (da) 1987-10-12
DK169760B1 (da) 1995-02-20
IL82149A (en) 1994-01-25
DK185287D0 (da) 1987-04-10
DE3787661D1 (de) 1993-11-11
JPS62242680A (ja) 1987-10-23
AT389875B (de) 1990-02-12
EP0241003A3 (en) 1988-10-12

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