KR850000413A - 아미노-피리딘 유도체의 제조방법 - Google Patents

아미노-피리딘 유도체의 제조방법 Download PDF

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KR850000413A
KR850000413A KR1019840003591A KR840003591A KR850000413A KR 850000413 A KR850000413 A KR 850000413A KR 1019840003591 A KR1019840003591 A KR 1019840003591A KR 840003591 A KR840003591 A KR 840003591A KR 850000413 A KR850000413 A KR 850000413A
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프람로즈 바그리 제한
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존. 지. 호스만
아메리칸 홈 프로닥트 코포레이숀
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • 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
    • C07D213/60—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 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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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
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    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D405/02—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 two hetero rings
    • C07D405/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
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    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

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Abstract

내용 없음.

Description

아미노-피리딘 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (8)

  1. (a) 일반식(IV)의 피리미딘을 일반식(V)의 아민과 반응시켜 일반식(I)에 상응하는 화합물을 수득하거나, (b) 일반식(Ⅲ)의 화합물을 일반식(V)의 아민과 반응시켜 일반식(VI)의 화합물을 수득하고, 일반식(VI) 화합물을 일반식(II)의 아미딘과 함께 축합시켜 일반식(I)에 상응하는 화합물을 수득하고, (c)필요에 따라서, R2가 옥소인 일반식(I) 화합물을 R2가 옥소인 일반식(I) 화합물의 나트륨염과 포스포로 우스 옥시클로라이드를 반응시켜 R2가 티옥소인 일반식(I)에 상응하는 화합물로 전환시켜서 일반식(VII)의 4-클로로피리미딘을 수득한 다음, 일반식(VII)의 4-클로로피리미딘을 수산화칼륨 및 유화수소의 에탄올수용액으로서 처리하여 일반식(I)에 상응하는 화합물을 수득하거나, 필요에 따라서, 일반식(VII)의 4-클로로피리미딘을 과잉의 암모니아가 함유된 불활성유기용매 용액으로서 처리하여 일반식(I)에 상응하는 화합물을 수득하고, (d) 필요에 따라서, R3가 시아노인 일반식(I)의 화합몰을 황산으로 가수분해하여 R3가 아미노카보닐인 일반식(I)에 상응하는 화합물을 수득함을 특징으로 하여 일반식(I)화합물 또는 임상학적으로 허용되는 이들 부가염을 제조하는 방법.
    상기 일반식(I)에 있어서, R1은 저급알킬, 사이클로(저급)알킬, 페닐(저급)알킬, 또는 트리플루오로메틸이고, R2는 옥소, 티옥소, 또는 이미노이고; R3는 시아노, 아미노 카보닐, 니트로, 메틸설포닐 또는 아미노설포닐이고; R4,R5,R6,R7및 R8는 각각 독립적으로 수소 또는 저급알킬이고; R9는 수소, 저급알케닐, 1-피페리디닐, 1-필로리디닐, 1-피페라지닐, 저급알키닐, 사이클로(저급)알킬, 2,3 또는 4-피리디닐, 2 또는 3-프라닐, 2 또는 3-인도릴, 2 또는 3-티에닐, 5-이미다조릴, 4-몰포리닐, 페닐, 페닐 모노- 또는 히드록시 혹은 저급 알콕시로서 이치환된 것, 이미다조릴, 4-티오몰포리닐, 피라지닐, 피리다지닐, 트리아지닐, 필로릴, 피라조릴, 티아조릴, 옥사디아조릴, 티아디아조릴, 이소자조릴, 프라조릴, 옥사티아조릴, 퀴노리닐, 이소-퀴노리닐, 피리도피리미디닐, 벤조자조릴, 벤지미다조릴, 벤조자지닐, 벤즈피로닐, 이소인도릴, 또는 인도라지닐이고; m 및 n는 각각 독립적으로 0 내지 2의 정수이며; 상기 일반식(II),(III),(IV),(V),(VI) 및 (VII)에 있어서, R2는 옥소이고, R3은 시아노, 니트로, 메틸설포닐 또는 아미노설포닐이고, R10은 저급알킬이고, 그외는 일반식(I)에서 정의된 바와 같다.
  2. 제1항에 있어서, R1이 저급알킬, 사이클로(저급) 알킬 또는 벤질이고; R2가 옥소, 티옥소 또는 이미노이고; R3가 시아노 또는 아미노카보닐이고; R4,R6및 R8가 각각 독립적으로 수소 또는 저급알킬이고; R9이 저급 알케닐, 사이클로(저급) 알킬, 2,3 또는 4-피리디닐, 2 또는 3-프라닐, 2 또는 3-인도릴, 2 또는 3-티에닐, 4-몰포리닐, 페닐 또는 페닐모노 또는 하이드록시 혹은 저급 알콕시로서 이치환된 것이고; m 및 n이 각각 독립적으로 0 내지 2의 정수이거나 또는 임상학적으로 허용되는 그들의 부가염인 방법.
  3. 제1항에 있어서, R1이 저급알킬, 사이클로(저급) 알킬 또는 벤질이고; R2가 옥소 또는 티옥소이고; R3가 시아노이고; R4,R5및 R7이 수소이고; R6및 R8가 각각 독립적으로 수소 또는 저급 알킬이고; R9이 저급알케닐, 2,3 또는 4-피리디닐, 2-프라닐, 3-인도릴, 3-티에닐, 4-몰돌리닐, 페닐 또는 페닐모노 또는 저급 알콕시로서 이치환된 것이고; m 및 n이 각각 독립적으로 0 내지 2의 정수이거나, 또는 임상학적으로 허용되는 그들의 부가염인 방법.
  4. 제1항에 있어서, 제조된 일반식(I)의 화합물이 1,4-디하이드로-2-메틸-4-옥소-6-[(3-피리디닐메틸)아미노]-5-피리미딘카보니트릴; 1,4-디하이드로-2-메틸-6- [N-메틸-N-(3-피리디닐메틸)-아미노]-4-옥소-5-피리미딘 카보니트릴; 1,4-디하이드로-2-메틸-4-옥소-6 -[(페닐에틸)아미노]-5-피리미딘카보니트릴; 1,4-디하이드로-2-메틸-4-옥소-6-[(2-피리디닐에틸)아미노]-5-피리미딘카보니트릴; 1,4 -디하이드로-2-메틸-4-옥소-6-[(4-피리디닐에틸)아미노]-5-피리미딘 카보니트릴; 1,4-디하이드로-2-메틸-4-옥소-6-[(2-피리디닐메틸)아미노]-5-피리미딘카보니트릴 ; 1,4-디하이드로-2-메틸-4-옥소-6-[(페닐메틸)아미노]-5-피리딘카보니트릴; 1,4-디하이드로-2-메틸-4-옥소-6-[2-(3-피리디닐)에틸아미노]-5-피리미딘카보니트릴; 1,4-디하이드로-2-메틸-4-옥소-6-[2-(4-피리디닐)에틸아미노]-5-피리미딘 카보니트릴; 1,4-디하이드로-2-메틸-6-[(3-피리디닐메틸)아미노]-4-티옥소-5-피리미딘카보니트릴; 1,4-디하이드로-2-에틸-4-옥소-6-[(3-피리디닐메틸)아미노]-5-피리미딘카보니트릴; 1,4-디하이드로-2-(1-메틸 에틸)-4-옥소-6-[(3-피리디닐메틸)아미노]-5-피리미딘카보니트릴; 2-사이클로프로필-1,4-디하이드로-4-옥소-6-[(3-피리디닐메틸)아미노]-5-피리미딘카보니트릴; 1,4-디하이드로-2-(1,4-디메틸에틸)-4-옥소-6-[(3-피리디닐에틸)아미노]-5-피리미딘카보닐; 1,4-디하이드로-4-옥소-2-페닐메틸-6-[(3-피리디닐메틸)아미노]-5-피리미딘카보니트릴; 1,4-디하이드로-2-메틸-4-옥소-6-[[1-(3-피리디닐)에틸]아미노]-5-피리미딘카보니트릴 또는 약제학적으로 허용되는 그들의 부가염인 방법.
  5. 제1항에 있어서, 제조된 일반식(I)의 화합물이 1,4-디하이드로-6-[(2-프라닐메틸)아미노]-2-메틸-4-옥소-5-피리미딘카보니트릴; 1,4-디하이드로-2-메틸-6-[[2-(4-몰포리닐)에틸]아미노]-4-옥소-5-피리미딘 카보니트릴; 1,4-디하이드로-2-메틸-4-옥소-6-[[2-(3-티에닐)에틸]아미노]-5-피리미딘카보니트릴; 1,4-디하이드로-6-[[2-(3,4-디메톡시페닐)에틸]아미노)-2-메틸-4-옥소-5-피리미딘카보니트릴; 1,4-디하이드로-6-[[2-(1H-인돌-3-일)에틸]아미노]-2-메틸-4-옥소-5-피리미딘카보니트릴; 1,4-디하이드로-2-메틸-4-옥소-6-[(2-프로페닐)아미노]-5-피리미딘카보니트릴 또는 약제학적으로 허용되는 그들의 부가염인 방법.
  6. 아래 일반식(I)의 화합물 또는 임상학적으로 허용되는 그들의 염을 약제학적으로 허용되는 담체와 함께 혼합하는 것을 특징으로 하여, 강심적인 약제학적 조성물을 제조하는 방법.
    상기식에서, R1은 저급알킬, 사이클로(저급)알킬, 페닐(저급) 알킬, 또는 트리플루오로 메틸이고; R2는 옥소, 티옥소, 또는 이미노이고; R3은 시아노, 아미노 카보닐, 니트로, 메틸설포닐 또는 아미노 설포닐이고; R4,R5,R6,R7및 R8는 각각 독립적으로 수소, 또는 저급알킬이고; R9는 저급알킬, 1-피페리디닐, 1-필로리디닐, 1-피페라지닐, 저급알키닐, 사이클로(저급)알릴, 2,3 또는 4-피리디닐, 2 또는 3-프라닐, 2-또는 3-인도릴, 2 또는 3-티에닐, 5-이미다조릴, 4-몰포리닐, 페닐, 페닐 모노-또는 히드록시 혹은 저급알콕시로서 이치환된 것, 이미다조릴, 4-티오몰포리닐, 피라지닐, 피리다지닐, 트리아지닐, 필로릴, 피라-조릴, 티아조릴, 옥사디아조릴, 티아디아조릴, 이소자조릴, 푸라조릴, 옥사티아조릴, 퀴노리닐, 이소퀴노리닐, 피리도피리미디닐, 벤조자조릴, 벤지미다조릴, 벤조자지닐, 벤즈피로닐, 이소인도릴 또는 인도라지닐이고; m 및 n는 각각 독립적으로 0 내지 2의 정수이다.
  7. 제6항에 있어서, 일반식(I)의 화합물이 제1항 내지 4항 어느 하나의 방법으로 제조하는 방법.
  8. 일반식(II)의 화합물을 일반식(III)의 화합물과 함께 축합하여 일반식(IV)의 화합물을 제조하는 방법.
    상기식에서, R1은 저급알킬, 사이클로(저급)알킬, 페닐(저급)알킬 또는 트리플루오로메틸이고; R3은 시아노, 니트로, 메틸설포닐 또는 아미노설포닐이고; R10은 저급알킬이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019840003591A 1983-06-30 1984-06-25 아미노-피리딘 유도체의 제조방법 Expired KR900001180B1 (ko)

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US06/509,887 US4507304A (en) 1983-06-30 1983-06-30 Use of 6-amino-5-pyrimidinecarbonitrile derivatives as cardiotonic agents
US509887/83 1983-06-30
US06/509,886 US4505910A (en) 1983-06-30 1983-06-30 Amino-pyrimidine derivatives, compositions and use
US509886/83 1983-06-30
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EP0530149A1 (de) * 1991-08-30 1993-03-03 Ciba-Geigy Ag Schädlingsbekämpfungsmittel
DE10238723A1 (de) 2002-08-23 2004-03-11 Bayer Ag Phenyl-substituierte Pyrazolyprimidine
DE10238722A1 (de) 2002-08-23 2004-03-11 Bayer Ag Selektive Phosphodiesterase 9A-Inhibitoren als Arzneimittel zur Verbesserung kognitiver Prozesse
DE10238724A1 (de) 2002-08-23 2004-03-04 Bayer Ag Alkyl-substituierte Pyrazolpyrimidine
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DE10320785A1 (de) 2003-05-09 2004-11-25 Bayer Healthcare Ag 6-Arylmethyl-substituierte Pyrazolopyrimidine
US8044060B2 (en) 2003-05-09 2011-10-25 Boehringer Ingelheim International Gmbh 6-cyclylmethyl- and 6-alkylmethyl pyrazolo[3,4-D]pyrimidines, methods for their preparation and methods for their use to treat impairments of perception, concentration learning and/or memory
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JP5498392B2 (ja) 2007-11-30 2014-05-21 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング １，５−ジヒドロ−ピラゾロ［３，４−ｄ］ピリミジン−４−オン誘導体及びｃｎｓ障害の治療のためのｐｄｅ９ａモジュレーターとしてのそれらの使用
UA105362C2 (en) 2008-04-02 2014-05-12 Бьорингер Ингельхайм Интернациональ Гмбх 1-heterocyclyl-1, 5-dihydro-pyrazolo [3, 4-d] pyrimidin-4-one derivatives and their use as pde9a modulators
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