KR960022438A - 나프틸옥시아세트산 유도체 - Google Patents

나프틸옥시아세트산 유도체 Download PDF

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KR960022438A
KR960022438A KR1019950056504A KR19950056504A KR960022438A KR 960022438 A KR960022438 A KR 960022438A KR 1019950056504 A KR1019950056504 A KR 1019950056504A KR 19950056504 A KR19950056504 A KR 19950056504A KR 960022438 A KR960022438 A KR 960022438A
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naphthyl
alkylene
oxy
acetic acid
alkyl
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유키 나가오
가즈히코 도리스
다카유키 마루야마
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우에노 도시오
오노 야쿠힝 고교 가부시키가이샤
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    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/40—Acylated substituent nitrogen atom
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
    • C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
    • C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
    • C07C235/18—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides
    • C07C235/20—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having at least one of the singly-bound oxygen atoms further bound to a carbon atom of a six-membered aromatic ring, e.g. phenoxyacetamides having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/32—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
    • C07C235/34—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton containing six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/66—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and singly-bound oxygen atoms, bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
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    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/26—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C243/28—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of a saturated carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/16—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms containing cyano groups and singly-bound oxygen atoms bound to the same carbon atom of an acyclic carbon skeleton
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings

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Abstract

본 발명은 하기 일반식(Ⅰ)의 나프틸옥시아세트산 유도체, 이의 무독성 염, 이의 무독성 산부가염 또는 이의 수화물에 관한 것인데, 상기 화합물들은 PGE2수용체에 결합하여 PGE2에 대한 길항 또는 작용 활성을 나타내므로, 이들은 PGE2길항물질 또는 PGE2작용물질로서 유용하다;
[상기 식에서, R1은 수소, 알킬, 알킬렌 - (-COOR10, -OH, -CONR4R5, -CHNR6- 알킬렌- OH, -NR4R5, -시아노 또는 테트라졸릴)이고; A는 단일결합, 알킬렌, 알케닐렌, -S-알킬렌, -O-알킬렌이고; B는 NR3CO, CONR3이고 ; R2는 (1) 알킬, (2) 알케닐, (3) 페닐, 시클로알킬, 나프틸 및 질소 원자를 함유하는 헤테로시클릭 고리(이때, 상기 고리는 1-3개의 알킬, 알콕시 및 할로겐 등에 의해 치환될 수 있음) 중 1-3개의 치환체로 치환된 알킬 또는 알케닐이고, (4) NR7R8또는 (5) 알킬렌 -NR7R8이다.)

Description

나프틸옥시아세트산 유도체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. 하기 일반식(Ⅰ)의 화합물, 이의 무독성 염, 이의 무독성, 산부가염 또는 이의 수화물
    [상기 식에서, R1은 (i)수소, (ⅱ) C1-4 알킬, (ⅲ) (C1-4 알킬렌)-COOR10(이때, R10은 수소 또는 C1-4 알킬임), (ⅳ) (C1-4 알킬렌)-OH, (ⅴ) (C4-4알킬렌)-CONR4R5(이때, R4및 R5는 각각 독립적으로 수소 또는 C1-4 알킬임.), (ⅵ) (C1-4 알킬렌)-CONR6-(C1-4 알킬렌)-OH(이때, R6는 수소 또는 C1-4 알킬임), (ⅶ) (C1-4 알킬렌)-NR4R5(이때, R4및 R5는 상기 정의한 바와 동일한 의미임), (ⅶ) (C1-4 알킬렌)-시아노 또는 (ⅸ) (C1-4 알킬렌)-테트라졸릴이고; A는 단일 결합, C1-6 알킬렌, C2-6 알케닐렌, -S-(C1-6 알킬렌) 또는 -O-(C1-6 알킬렌)이고, B는 NR3CO 또는 CONR3(이때, R3은 수소 또는 C1-4 알킬임), R2는 (ⅰ) C1-6 알킬, (ⅱ) C2-6 알케닐, (ⅲ) 페닐, C4-7 시클로알킬, 나프틸 및 하나의 질소 원자를 함유하는 구성 원소가 4-7개인 헤테로시클릭 고리로부터 선택되는 1-3개의 치환분(들)에 의해 치환되는 C1-6 알케닐, (ⅳ) 페닐, C4-7 시클로알킬, 나프틸 및 하나의 질소 원자를 함유하는 구성 원소가 4-7 개인 헤테로시클릭 고리로부터 선택되는 1-3개의 치환분(들)에 의해 치환되는 C2-6 알케닐, (ⅴ) NR7R8(이때, R7및 R8은 각각 독립적으로 페닐, C4-7 시클로알킬, 나프틸 및 하나의 질소 원자를 함유하는 구성원소가 4-7개인 헤테로시클릭 고리임) 또는 (ⅵ) (C1-6 알킬렌)- NR7R8(이때, R7및 R8은 상기 정의한 바와 동일한 의미임), 단, R2내의 고리는 C1-4 알킬, C1-4 알킬, C1-4 알콕시, 할로겐, 니트로 또는 트리플루오로메틸중 1-3개에 의해 치환될 수 있음.]
  2. 제1항에 있어서, R1이 (C1-4 알킬렌)-COOR10인 화합물.
  3. 제1항에 있어서, R1은 수소, C1-4 알킬, (C1-4 알킬렌)-OH, (C1-4 알킬렌)-CONR4R5, (C1-4 알킬렌)-CONR6-(C1-4 알킬렌)-OH, (C1-4 알킬렌)-NR4R5, (C1-4 알킬렌)-시아노 또는 (C1-4 알킬렌)-테트라졸릴인 화합물.
  4. 제2항에 있어서, R2가 (ⅰ) C1-6 알킬, (ⅱ) C2-6 알케닐, (ⅲ-a) 페닐, C4-7 시클로알킬 및 나프틸로 구성되는 군으로부터 선택되는 1-3개의 치환분(들)에 의해 치환되는 C1-6 알킬, (ⅳ-a) 페닐, C4-7 시클 로알킬 및 나프틸로 구성되는 군으로부터 선택되는 1-3개의 치환분(들)에 의해 치환되는 C2-6 알케닐, (ⅴ-a)NR7aR8a(이때, R7a및 R8a은 각각 독립적으로 페닐, C4-7 시클로알킬 또는 나프틸임) 또는 (ⅵ-a) (C1-6 알킬렌)-NR7aR8a(이때, R7a및 R8a은 상기 정의한 바와 동일한 의미임)인 화합물.
  5. 제2항에 있어서, R2가 (ⅲ-b) 본질적인 치환분으로서 하나의 질소 원자를 함유하고, 추가의 기를 함유하지 않거나 페닐, C4-7 시클로알킬, 나프틸 및 하나의 질소 원자를 함유하는 구성 요소가 4-7개인 헤테로시클릭 고리로부터 선택되는 추가 치환분으로서의 추가 기(들)을 하나 또는 두 개 함유하는 구성원소가 4-7개인 하나의 헤테로시클릭 고리에 의해 치환된 C1 알킬, (ⅳ-b) 본질적인 치환분으로서 하나의 질소 원자를 함유하고, 추가의 기를 함유하지 않거나 페닐, C4-7 시클로알킬, 나프틸 및 하나의 질소 원소를 함유하는 구성원소가 4-7개인 헤테로시클릭 고리로부터 선택되는 추가 기(들)을 추가 치환분으로서 하나 또는 두 개 함유하는 구성원소가 4-7개인 하나의 헤테로시클릭 고리에 의해 치환된 C2-6 알케닐, (ⅴ-b) NR7bR8b(이때, R7b및 R8b중 하나는 페닐, C4-7 시클로알킬, 나프틸 및 하나의 질소 원자를 함유하는 구성원소가 4-7개인 헤테로시 클릭 고리이며, 나머지는 하나의 질소 원자를 함유하는 구성원소가 4-7개인 헤테로시클릭 고리 또는 (ⅵ-b)(C1-6 알킬렌)-NR7bR8b(이때, R7b및 R8b는 상기 정의한 바와 동일한 의미임)인 화합물.
  6. 제4항에 있어서, [5-[(2-디페닐메틸아미노카르보닐에틸)나프틸-1-옥시]아세트산, [5-[2-(3,3-디페닐카르바조일)에틸]나프틸-1-옥시]아세트산, [5-[(2-디페닐메틸아미노카르보닐메톡시)나프틸-1-옥시]아세트산, [5-[(3,3-디페닐카르바조일)메톡시]나프틸-1-옥시]아세트산, [5-(디페닐메틸아미노카르보닐메틸)나프틸-1-옥시]아세트산, [5-(디페닐메틸아미노카르보닐)나프틸-1옥시]아세트산,[6-(디페닐메틸아미노카르보닐메틸)나프틸-1-옥시]아세트산, [6-(페닐메틸아미노카르보닐메틸)나프틸-1-옥시]아세트산, [5-(2-페닐에틸아미노카르보닐에틸]나프틸-1-옥시]아세트산, [5-(디페닐메틸아미노카르보닐)나프틸-1-옥시]아세트산, [6-(2-디페닐메틸아미노카르보닐에틸)나프틸-1-옥시]아세트산 또는 [5-[2-((1R-페닐-1-페닐에틸)아미노카르보닐에틸]나프틸-1-옥시]아세트산 [5-[2-((1S)-1-페닐에틸)아미노카르보닐]나프틸-1-옥시]아세트산, [5-[2-[N-디페닐메틸-N-에틸아미노카르보닐)에틸]나프틸-1-옥시]아세트산, [5-[2-(디페닐메틸아미노카르보닐)비닐]나프틸-1-옥시]아세트산, [5-[2-(디페닐메틸카르보닐아미노)에틸]나프틸-1-옥시]아세트산 또는 [5-[2-[1-페닐-1-(3-클로로페닐)메틸]아미노카르보닐에틸]나프틸-1-옥시]아세트산 또는 이의 메틸 에스테르인 화합물.
  7. 제5항에 있어서, [5-[2-[1-페닐-1-(3-피리딜)메틸]아미노카르보닐에틸]나프틸-1-옥시]아세트산 또는 이의 메틸 에스테르인 화합물.
  8. 제3항에 있어서, 1-메톡시-5-(2-디페닐메틸아미노카르보닐에틸)나프탈렌, 2-[5-(2-디페닐메틸아미노카르보닐에틸)나프틸-1-옥시]에탄올, [5-(2-디페닐메틸아미노카르보닐에틸)나프틸-1-옥시]아세트산 아미도, N,N-디메틸-[5-(2-디페닐메틸아미노카르보닐에틸)나프틸-1-옥시]아세트산 아미드, N-(2-히드록시에틸)-[5-(2-디페닐메틸아미노카르보닐에틸)나프틸-1-옥시]아세트산 아미드, 2-[5-(2-디페닐메틸아미노카르보닐에틸)나프틸-1-옥시]에틸아민, 5-[2-(디페닐메틸카르보닐아미노)에틸]나프트-1-올, 5-(2-디페닐메틸아미노카르보닐에틸)나프트-1-올, 1-시아노메톡시-5-(2-디페닐메틸아미노카르보닐에틸)나프탈렌, 1-테트라졸릴메톡시-5-(2-디페닐메틸아미노카르보닐에틸)나프탈렌, 1-메톡시-5-[2-[1-페닐-1-(3-클로로페닐)메틸]아미노카르보닐에틸]나프탈렌, 5-[2-[1-페닐-1-(3-클로로페닐)메틸]아미노카르보닐에틸]나프트-1-올 또는 1-시아노메특시-5-[2-[1-페닐-1-(3-클로로페닐)메틸]아미노카르보닐에틸]나프탈렌인 화합물.
  9. 제1항에 따른 일반식(Ⅰ)의 나프틸옥시아세트산 유도체, 이의 무독성염, 이의 무독성 산부가염 또는 이의 수화물의 유효량 및 약학적으로 허용가능한 담체 및/또는 피막을 함유하는, 낙태, 통중, 설사, 하제, 궤냥 위염, 고혈압 또는 혈전증의 치로 및/또는 예방, 또는 낙태 또는 수면 유도에 사용되는 약학 조성물.
    ※ 참고사항:최초출원 내용에 의하여 공개하는 것임.
KR1019950056504A 1994-12-28 1995-12-26 나프틸옥시아세트산유도체 KR100384261B1 (ko)

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US6335459B1 (en) 1998-12-23 2002-01-01 Syntex (U.S.A.) Llc Aryl carboxylic acid and aryl tetrazole derivatives as IP receptor modulators
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