KR850004095A - 아세틸렌 유도체의 제조방법 - Google Patents

아세틸렌 유도체의 제조방법 Download PDF

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KR850004095A
KR850004095A KR1019840007268A KR840007268A KR850004095A KR 850004095 A KR850004095 A KR 850004095A KR 1019840007268 A KR1019840007268 A KR 1019840007268A KR 840007268 A KR840007268 A KR 840007268A KR 850004095 A KR850004095 A KR 850004095A
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carbon atoms
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로버트 카슨 죤
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에취. 아이. 쉐르만
맥네이랩 인코포레이티드
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Abstract

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아세틸렌 유도체의 제조방법
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Claims (9)

  1. 하기 일반식(Ⅴ)의 화합물을 일반식 Ar―C≡C―H의 화합물과 커플링 시키거나, 하기 일반식(Ⅵ)의 화합물을 일반식 R1R2NH의 아민으로 무촉매환원적 알킬화시키거나, R1이 알킬, 시클로알킬 또는 시클로 알킬알킬인 일반식(Ⅰ)의 화합물을 제조하기 위해 R1이 수소인 일반식(Ⅰ)의 화합물을 환원적 알킬화시킴을 특징으로 하여, 하기 일반식(Ⅰ)의 아세틸렌, 약학적으로 허용되는 이의 산부가염 및 이의 제4암모늄 화합물을 제조하는 방법.
    상기식에서, Y는 독립적으로, 알킬, 알콕시, 알킬티오, 알킬술피닐, 알킬술포닐, 알카노일옥시, 알카노일아미노, 아미노, 모노알킬아미노, 디알킬아미노, 히드록시, 할로겐 또는 시아노이거나 인접한 고리탄 소상에서 메틸렌디옥시 또는 에틸렌디옥시를 형성하고, m은 0,1,2 또는 3이고, Ar은 고리탄소를 통해 아세틸렌 잔기에 결합된 페닐 또는 5―또는 6―원 복소환식 방향족 고리(이 고리들은, 독립적으로 알킬, 알콕시알킬티오, 알킬술피닐, 알킬술포닐, 카복스아미도, 할로겐, 플루오로알킬 또는 시아노중의 하나이상으로 치환될 수 있다)이고, R1및 R2는 독립적으로 수소, 알킬, 시클로, 알킬 또는 시클로알킬알킬이거나 R1및 R2가 알킬이며, 결합하여 산소 또는 황원자 또는 NR5잔기(여기서 R5는 수소 또는 알킬이다.)를 함유할 수 있는 5―내지 7―원 포화―고리를 형성하고, R3는 수소, 알킬 또는 알콕시 알킬이고, R4는 수소 또는 알킬이며, n은 0,1 또는 2이고, X는 브롬 또는 요오드이다.
  2. 제1항에 있어서, Y가 탄소수 약 1내지 6의 알킬; 탄소수 약 1내지 6의 알콕시; 탄소수 약 1내지 6의 알킬디오; 탄소수 약 1내지 6의 알킬술피닐; 탄소수 약 1내지 6의 알킬술포닐; 탄소수 약 2내지 6의 알카노일옥시; 탄소수 약 2내지 6의 알카노일아미노; 아미노; 탄소수 약 1내지 6모노알킬아미노; 탄소수 약 2내지 12의 디알킬아미노; 히드록시; 플루오로, 클로로 또는 브로모; 시아노; 또는 인접한 고리탄소상에서 메틸렌 디옥시 또는 에틸렌 디옥시를 형성하고; m은 0,1,2 또는 3이고, Ar이 고리탄소를 통해 아세틸렌 잔기에 결합되며 1,2 또는 3의 질소, 황 또는 산소원자를 함유하는 페닐 또는 5―또는 6―원 복소환식 방향족 고리 (이 고리들은 C1―C6알킬, C1―C6알킬시, C1―C6알킬티오, 탄소수 약 1내지 6의 알킬술피닐, 탄소수 약 1내지 6의 알킬술포닐, 카복스아미도, 플루오로, 클로로, 브로모, 요오도, 탄소수 약 1내지 6의 플루오로알킬 또는 시아노중의 하나이상으로 치환될 수 있다.)이고; R1및 R2가 수소; 탄소수 약 1내지 8의 알킬; 탄소수 약 3내지 6의 시클로알킬; 또는 탄소수 약 4 내지 7의 시클로알킬알킬이거나; R1및 R2가 알킬이며 결합하여 산소 또는 황원자 또는 NR5잔기 (여기서 R5가 수소 또는 탄소수 약 1내지 6의 알킬이다)를 함유할 수 있는 5―내지 7―원 포화―고리를 형성하고; R3가 수소; 탄소수 약 1내지 6의 알킬; 또는 각 알칼잔기의 탄소수가 약 1내지 6인 알콕시알킬이고; R4가 수소; 또는 탄소수 약 1내지 6의 알킬이며, n이 0,1 또는 2인 방법.
  3. 제1항에 있어서, 언급된 Ar중 5―또는 6―원 복소환식 고리가 티오펜, 피롤, 푸란, 피라졸, 이미다졸, 트리아졸, 옥사졸, 티아졸, 티아디아졸, 피리딘, 피리다진, 피리미딘, 피라진 및 트리아진중에서 선택되며 언급된 R1및 R2로부터 형성된 고리가 1―피롤리디닐, 4―탄소수 약 1내지 6의 알킬 피페라지닐 및 1―모르폴리노중에서 선택되는 방법.
  4. 제1항에 있어서, Y가 알콕시이고, m이 1,2 또는 3인 방법.
  5. 제1항에 있어서, R3및 R4중 적어도 하나가 수소가 아닌 방법.
  6. 제1항에 있어서, R1및 R2가 알킬인 방법.
  7. 제1항에 있어서, 언급된 약학적으로 허용되는 산부가염이 염산, 브롬화수소산, 요오드화수소산, 황산, 인산, 푸마르산, 말레산, 시클로헥실술팜산, 시트르산, 락트산 및 메탄술폰산, 중에서 선택된 산으로 부터 형성되며 언급된 제4암모늄 화합물이 알킬 할라이드 또는 알킬술페이트로부터 형성된 화합물인 방법.
  8. 제1항에 있어서, Y가 아세틸렌잔기에 대해 파라위치에 있는 메톡시이고; m이 1이고; Ar이 페닐이고; R4가 수소이고; n이고; R3가 메틸이고; R1가 메틸이며; R2가 n―헥실인 방법.
  9. 제1항에 있어서, Y가 메톡시이고, m이 1인 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840007268A 1983-11-21 1984-11-20 아세틸렌 유도체의 제조방법 KR850004095A (ko)

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CA1300632C (en) * 1984-02-06 1992-05-12 John Robert Carson Acetylene amines and their use as vasodilators and antihypertensives
US4663334A (en) * 1985-12-11 1987-05-05 Mcneilab, Inc. Heteroaromatic acetylenes useful as antihypertensive agents
PT85081A (en) * 1986-06-19 1987-07-01 Smithkline Beckman Corp Irreversible dopamine-beta-hydroxylase inhibitors
US4772755A (en) * 1987-03-19 1988-09-20 Mcneilab, Inc. 1,2-1,4 addition reaction sequence leading to disubstituted acelylenes
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FR2508453A1 (fr) * 1981-06-30 1982-12-31 Sanofi Sa Procede de preparation de derives des (thienyl-2)- et thienyl-3)-2 ethylamines et produits ainsi obtenus

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