KR870002122A - 1,4-디하이드로피리딘 유도체의 제조방법 - Google Patents

1,4-디하이드로피리딘 유도체의 제조방법 Download PDF

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KR870002122A
KR870002122A KR1019850005902A KR850005902A KR870002122A KR 870002122 A KR870002122 A KR 870002122A KR 1019850005902 A KR1019850005902 A KR 1019850005902A KR 850005902 A KR850005902 A KR 850005902A KR 870002122 A KR870002122 A KR 870002122A
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레홉 아키발트 죤
제임스 워드 테렌스
오팔코 앨버트
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데이비드 에릭 기벤스
죤 와이어스 앤드 브라더 리미티드
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Abstract

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Description

1,4-디하이드로피리딘 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (26)

  1. 일반식(Ⅱ),(Ⅲ) 및 (Ⅳ)의 화합물을 반응시키거나, 일반식(Ⅱ)의 화합물을 일반식(Ⅴ)의 화합물과 반응시키거나, ArCHO, 일반식(Ⅵ) 및 (Ⅴ)의 화합물을 반응시키거나, 일반식(Ⅶ)의 화합물을 일반식(Ⅷ)의 화합물과 반응시켜 각각에 상응하는 일반식(I)의 화합물을 제조하거나, R이 수소인 일반식(I)의 화합물을 강염기의 존재하에 일반식 R-Z3(여기서, R은 하기 정의한 바와 같으며 수소는 아니고, Z3는 할로겐 또는 설포닐옥시 그룹이다)의 알킬화제로 알킬화하여 상응하는 일반식(I)의 화합물을 제조하거나, 에스테르 그룹을 갖는 일반식(I)의 화합물을, 경우에 따라서는 선택적으로 가수분해시켜 카복실그룹을 갖는 일반식(I)의 화합물을 제조하거나, 카복실그룹을 갖는 일반식(I)의 화합물을 에스테르화시켜 에스테르그룹을 갖는 일반식(I) 화합물의 제조하거나, 카복실그룹을 갖는 일반식(I)의 화합물을 염기와 반응시켜 그의 염을 생성하거나 일반식(I) 화합물의 카복실레이트 염을 산성화시켜 유리산을 생성하거나, 일반식(I)의 화합물에 산을 가하여 산부가염으로 전환시키거나 산부가염을 염기성화시켜 일반식(I)의 화합물을 생성하거나, 염기성 치환체을 갖는 일반식(I)의 화합물을 알킬화제와 반응시켜 4급 암모늄염으로 전환시킴을 특징으로 하여, 일반식(I)의 화합물 또는 그의 염을 제조하는 방법.
  4. 상기식에서, Ar는 임의치환된 아릴 라디칼이고, R은 수소 또는 임의 치환된 알킬 또는 아르알킬 그룹이고, R1과 R2는 동일하거나 상이하며, 수소이거나 할로겐, 하이드록시, 카복시, 시아노, 알콕시, 알킬티오, 아릴옥시, 알콕시카보닐, 아미노, 치환된 아미노 및 임의 치환된 아릴로부터 선택된 하나 이상의 그룹으로 임의치환된, 포화 또는 불포화, 사이클릭 또는 아시이클릭 지방족 탄화수소 잔기이고, A는 -XR3그룹이고, 여기서 X는 일반식 -(CHR6)p-Y-(CHR7)q-의 그룹이거나 일반식 -(CHR6)r-O-(CHR7)s- 그룹이고 (여기서, Y는 -S-, NR8또는 직접 결합이고, p와 q는 Y가 직접 결합일 경우 둘다 0이 아닌 조건하에 각각 0,1 또는 2이고, r과 s중의 하나는 0,1 또는 2이고, 그 나머지는 0이며, R6,R7및 R8은 독립적으로 수소 또는 저급알킬이고, R3는 산소, 질소 또는 황으로부터 선택된 다른 환 헤테로원자를 임의로 포함하는 임의 치환된 질소환 헤태로아릴 라디칼이다), B는 수소, 카복실 또는 저급 알콕시카보닐이거나, 저급알콕시, 카복실, 저급알콕시카보닐 또는 아미노로임의 치환된 저급알킬, 또는 1 내지 2개의 저급알킬그룹으로 임의 치환된 아미노이고, 상기 일반식(Ⅱ) 및 (Ⅳ)에서, T1및 T2중의 하나는 A이며 다른 하나는 B이고, 단 이때 a) r이 0일 수 없고, b) Y가 -S- 또는 -NR8-인 경우 p는 1 또는 라는 조건하에 A는 상기 정의한 바와 같고 B는 수소, 카복실, 저급 알콕시카보닐 또는 임의 치환된 저급 알킬이고, 상기 일반식(Ⅱ),(Ⅴ) 및 (Ⅵ)에서, T2가 A일때 T1이 임의 치환된 아미노일 수 없다는 조건하에 T1및 T2중의 하나는 A이고 다른 하나는 B이며, 단 이때 a) r이 0일 수 없고, b) Y가 -S- 또는 -NR8-인 경우 p는 1 또는 2라는 조건하에 A 및 B는 상기 정의한 바와 같으며, 상기 일반식(Ⅶ) 및 (Ⅷ)에서, Z1및 Z2중의 하나는 할로겐 또는 설포닐옥시그룹이고, 그 나머지는 경우에 따라 -YH, -Y, -OH 또는 -O(여기서 Y는 상기 정의한 바와같다)이고, V 및 W는 각각 0,1 또는 2이며, 단 이때 (i) V가 2이고 Z2가 -YH 또는 -Y인 경우에 Z1은 디알킬아미노 또는 4급 암모늄그룹일 수 있고, (ⅱ) Z1또는 Z2중의 하나가 -OH 또는 -O인 경우에, V 및 W 중의 하나는 0이다.
  5. 제1항에 있어서, R3가 환원자 5 내지 10개를 함유하는 모노-또는 비-사이클릭 질소환 헤테로 아릴라디칼인 방법.
  6. 제2항에 있어서, R6가 이미다졸릴, 피리딜, 티아졸릴, 피롤릴, 벤즈이미다졸릴, 퀴놀릴, 이소퀴놀릴 또는 이미다조피리딜인 방법.
  7. 제1항 내지 제3항중 어느 하나에 있어서, X가 -NH-, -O-, -S-, -CH2-, -CH(CH3)-, -CH(CH3)CH2-, -CH2CH(CH3)-, -OCH2-, -CH2O-, -(CH2)2O- 또는 일반식 -CH-Z-CH2-, -(CH2)2-Z-CH2- 또는 -CH2-Z-(CH2)2-의 그룹(여기서 Z는 S,NH 또는 직접 결합이다)인 방법.
  8. 제1항 내지 제4항중 어느 하나에 있어서, Ar가 임의 치환된 페닐, 피리딜, 퀴놀릴 또는 벤즈이미다졸릴인 방법.
  9. 제5항에 있어서, Ar가 2- 또는 3-니트로페닐, 2,3-디클로로페닐, 2-트리풀루오로메틸페닐, 펜타플루오로페닐, 나프틸, 피리딜 또는 할로피리딜인 방법.
  10. 제1항 내지 제6항중 어느 하나에 있어서, B가 H,CH3-,NH2-,NMe2-,NH2CH2-,CH3CH2-,CH3OCH2-,CH3OOC-,HOOC-,HOOCCH2- 또는 CH3OOCH2-인 방법.
  11. 제1항 내지 제7항중 어느 하나에 있어서, 제조된 화합물중의 R이 수소, 메틸, 에틸, n-프로필, 이소프로필, 벤질, 카브에톡시메틸 또는 카브메톡시메틸인 방법.
  12. 제1항 내지 제8항중 어느 하나에 있어서, 제조된 화합물중의 R1및/또는 R2가 수소이거나, 환원자수 5 내지 10의 아릴, 저급알콕시, 아미노, 디저급-알킬아미노, 카복시 또는 저급 알콕시카보닐로 임의 치환된, 탄소수 1 내지 6의 포화 또는 불포화 아사이클릭 탄화수소쇄인 방법.
  13. 제1항 내지 제9항중 어느 하나에 있어서, 제조된 화합물중의 R1및/또는 R2가 수소, 메틸, 에틸, n-프로필, 이소프로필, 부틸, 메톡시메틸, 에톡시메틸, 메톡시, 프로필, 아미노메틸, 2-아미노에틸, 3-아미노프로필, 디메틸아미노에틸, 2-카복시에틸, 메톡시카보닐메틸, 에톡시카보닐메틸, 피리딜메틸, 피리딜에메, 이미다졸릴메틸 또는 이미다졸릴에틸인 방법.
  14. 제1항에 있어서, 제조된 일반식(I)의 화합물이 다음과 같은 화합물 또는 약제학적으로 허용 가능한 그의 염인 방법.
  15. 1,4-디하이드로-2-(이미다졸-1-일메틸)-6-메틸-4-(3-니트로페닐)피리딘-3,5-디카복실산 3-에틸-5-메틸 디에스테르,
  16. 1,4-디하이드로-2-[2-(이미다졸-1-일)-에틸]-6-메틸-4-(2-니트로페닐)피리딘-3,5-디카복실산디에메 에스테르,
  17. 1,4-디하이드로-2-[2-(1-이미다졸릴)에틸]-6-메틸-4-(2-니트로페닐)피리딘-3,5-디카복실산디메틸에스테르,
  18. 1,4-디하이드로-2-메틸-4-(3-니트로페닐)-6-[(3-피리딜옥시)메틸]피리딘-3,5-디카복실산 5-에틸-3-메틸 디에스테르,
  19. 2-[2-(1-벤즈이미다졸릴)에틸]-4-[2,3-디클로로페닐]-1,4-디하이드로-6-메틸피리딘-3,5-디카복실산 디메틸 에스테르,
  20. 4-(2,3-디클로로페닐)-1,4-디하이드로-2-메틸-6-(2-[2-메틸(1-이미다졸릴)]에틸) 피리딘-3,5-디카복실산 디메틸 에스테르,
  21. 4-(2,3-디클로로페닐)-1,4-디하이드로-2-[2-(1-이미다졸릴)에틸]-6-메틸피리딘-3,5-디카복실산 디메틸 에스테르,
  22. 1,4-디하이드로-2-[2-(1-이미다졸릴)에틸]-6-메틸-4-(3-니트로페닐)피리딘-3,5-디카복실산디에틸 에스테르,
  23. 1,4-디하이드로-2-(1-이미다졸릴메틸)-6-메틸-4-(3-니트로페닐)피리딘-3,5-디카복실산 디메틸에스테르,
  24. 1,4-디하이드로-2-(이미다졸-1-일메틸)-6-메틸-4-(3-니트로페닐)피리딘-3(5-디카복실산 3-에틸-5-이소프로필 디에스테르, 또는
  25. 1,4-디하이드로-2-(이미다졸-1-일메틸)-6-메틸-4-(퀴놀-4-일)피리딘-3,5-디카복실산 3-에틸-5-메틸 디에스테르.
  26. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019850005902A 1984-08-17 1985-08-16 1,4-디하이드로피리딘 유도체의 제조방법 KR930000167B1 (ko)

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GB848421039A GB8421039D0 (en) 1984-08-17 1984-08-17 Heterocyclic compounds
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HU194868B (en) 1988-03-28
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