KR960705780A - 평활근 이완제로서의 디아미노사이클로부텐-3.4-디온(Diaminocyclobutene-3.4-diones as smooth muscle relaxants) - Google Patents

평활근 이완제로서의 디아미노사이클로부텐-3.4-디온(Diaminocyclobutene-3.4-diones as smooth muscle relaxants) Download PDF

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KR960705780A
KR960705780A KR1019960702542A KR19960702542A KR960705780A KR 960705780 A KR960705780 A KR 960705780A KR 1019960702542 A KR1019960702542 A KR 1019960702542A KR 19960702542 A KR19960702542 A KR 19960702542A KR 960705780 A KR960705780 A KR 960705780A
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안토니 부테라 죤
아담 앤테인 슈일러
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이곤 이. 버그
아메리칸 홈 프로덕츠 코포레이션
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Abstract

일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염은 평활근 이완제이다.
상기 식에서, R1및 R2는 독립적으로 수소, 직쇄 또는 측쇄 알킬이거나, 모노- 또는 비-사이클릭 알킬이고, A는 알킬, 퍼플루오로알킬, 알콕시, 퍼플루오로알콕시, 아미노, 알킬아미노, 디알킬아미노, 알킬설폰아미도, 알킬카복스아미도, 니트로, 시아노 또는 카복실에 의해 치환될 수 있는 N-헤테로사이클이거나, A는 시아노, 니트로, 알킬, 퍼플루오로알킬, 알콕시, 퍼플루오로알콕시, 아미노, 알킬아미노, 디알킬아미노, 설파밀, 알킬설폰아미도, 아릴카복스아미도, 알킬설포닐, 퍼플루오로알킬설포닐, 아릴설포닐, 클로로, 브로모, 플루오로, 요오도, 1-이미다졸릴 또는 카복실 중에서 선택된 1 또는 2개의 치환제를 함유하는 치환된 페닐 그룹이다.

Description

평활근 이완제로서의 디아미노사이클로부텐-3.4-디온(Diaminocyclobutene-3.4-diones as smooth muscle relaxants)
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Claims (15)

  1. 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염.
    상기 식에서, R1및 R2는 서로 독립적으로 수소, C1-10직쇄 알킬, C1-10측쇄 알킬 또는 C3-10사이클릭 또는 비사이클릭이 알킬이고, A는
    로 이루어진 그룹(여기서, R3은 수소, C1-6알킬, C1-6퍼플루오로알킬, C1-6알콕시, C1-6퍼플루오로알콕시, 아미노, C1-6알킬아미노, C2-12디알킬아미노, C1-6알킬설폰아미도, C2-7알킬카복스아미도, 니트로, 시아노, 또는 카복실이다)으로부터 선택되거나, A는 일반식의 치환된 페닐 그룹(여기서, R4및 R5는 서로 독립적으로 시아노, 니트로, 아미노, C1-6알킬, C1-6퍼플루오로알킬, C1-6알콕시, C1-6퍼플루오로알콕시, 아미노, C1-6알킬아미노, C2-12디알킬아미노, 설파밀, C1-6알킬설폰아미도, C6-12알킬설폰아미도, C2-7알킬카복스아미도, C7-13아릴카복스아미도, C1-6알킬설포닐, C1-6퍼플루오로알킬설포닐, C6-12아릴설포닐, 클로로, 브로모, 플루오로, 요오도, 1-이미다졸릴, 카복실 및 수소로 이루어진 그룹으로부터 선택되고, 단, R4및 R5는 동시에 수소일 수 없다)이다.
  2. 제1항에 있어서, A가
    로 이루어진 그룹으로부터 선택되거나, A가 일반식의 치환된 페닐 그룹(여기서, R4및 R5는 서로 독립적으로 시아노, 니트로, 아미노, 클로로, 브로모, 플루오로, 요오도, 1-이미다졸릴, 카복실 또는 수소로 이루어진 그룹으로부터 선택되고, 단 R4및 R5는 동시에 수소일 수 없다)인 화합물 또는 이의 약제학적으로 허용되는 염.
  3. 제1항에 있어서, A가
    로 이루어진 그룹으로부터 선택되거나, A가 일반식의 치환된 페닐 그룹(여기서, R4및 R5는 서로 독립적으로 시아노, 니트로, 아미노, 클로로, 브로모, 플루오로, 요오도, 1-이미다졸릴, 카복실 및 수소로 이루어진 그룹으로부터 선택되고, 단 R4및 R5는 동시에 수소일 수 없다)인 화합물 또는 이의 약제학적으로 허용되는 염.
  4. 알킬 그룹의 탄소수가 1 내지 6이고 페닐 그룹이 1 또는 2개의 시아노, 니트로, 아미노, 할로 또는 카복실 그룹에 의해 치환된 3-알킬아미노-4-[(치환된 페닐)아미노]-사이클로부트-3-엔-1,2-디온.
  5. 제1항에 있어서, 3-(피라딘-4-일아미노)-4-(1,2,2-트리메틸-프로필아미노)-사이클로부트-3-엔-1,2-디온; (엑소)-3-(비사이클로[2.2.1]헵트-2-일아미노)-4-(피리딘-4-일아미노)-4-사이클로부트-3-엔-1,2-디온; 3-(피리딘-3-일아미노)-4-(1,2,2-트리메틸-프로필아미노)-사이클로부트-3-엔-1,2-디온; 3-(2-메틸에틸아미노)-4-(피리딘-3-일아미노)(사이클로부트-3-엔-1,2-디온; 3-디메틸아미노-4-(피리딘-3-일아미노)-사이클로부트-3-엔-1,2-디온; 3-아미노-4-(피리딘-3-일아미노)-사이클로부트-3-엔-1,2-디온 또는 3-3급-부틸아미노-4-(피리딘-3-일아미노)-사이클로부트-3-엔-1,2-디온인 화합물.
  6. 제1항에 있어서, 3-3급-부틸아미노-4-(이소퀴놀린-5-일아미노)- 사이클로부트-3-엔-1,2-디온; 3-아미노-4-(이소퀴놀린-5-일아미노)-사이클로부트-3-엔-1,2-디온; 3-(퀴놀린-8-일아미노)-4-(1,2,2-트리메틸-프로필아미노)-사이클로부트-3-엔-1,2-디온; 3-메틸아미노-4-(퀴놀린-8-일아미노)-사이클로부트-3-엔-1,2-디온; 3-아미노-4-(퀴놀린-8-일아미노)-사이클로부트-3-엔-1,2-디온; 3-(퀴놀린-3-일아미노)-4-(1,2,2-트리메틸-프로필아미노)-사이클로부트-3-엔-1,2-디온; 3-3급-부틸아미노-4-(퀴놀린-3-일아미노)-사이클로부트-3-엔-1,2-디온; 3-(퀴놀린-3-일아미노)-4-(1,1-디메틸-프로필아미노)-사이클로부트-3-엔-1,2-디온; 3-(6-메톡시-퀴놀린-8-일아미노)-4-(1,2,2-트리메틸-프로필아미노)-사이클로부트-3-엔-1,2-디온; 3-(6-메톡시-퀴놀린-8-일아미노)-4-메틸아미노-사이클로부트-3-엔-1,2-디온; 3-3급-부틸아미노-4-(퀴놀린-6-일아미노)-사이클로부트-3-엔-1,2-디온 또는 3-(이소퀴놀린-5-일아미노)-4-메틸아미노-사이클로부트-3-엔-1,2-디온인 화합물.
  7. 제1항에 있어서, 3-3급-부틸아미노-4-(1H-인다졸-6-일아미노)-사이클로부트-3-엔-1,2-디온; (엑소)-4-[2-(비사이클로[2.2.1]헵트-2-일아미노)-3, 4-디옥소-사이클로부트-1-에닐아미노]-벤조니트릴; 또는 4-[3,4-디옥소-2-(1,2,2-트리메틸-프로필아미노)-사이클로부트-1-에닐아미노]-벤젠설폰아미드인 화합물.
  8. 제1항에 있어서, 4-[3,4-디옥소-2-(1,2,2-트리메틸-프로필아미노)-사이클로부트-1-에닐아미노]-벤조니트릴인 화합물.
  9. 제1항에 있어서, (+)-(R)-4-[3,4-디옥소-2-(1,2,2-트리메틸-프로필아미노)-사이클로부트-1-에닐아미노]-3-에틸-벤조니트릴인 화합물.
  10. 제1항에 있어서, (+)-(R)-4-[3,4-디옥소-2-(1,2,2-트리메틸-프로필아미노)-사이클로부트-1-에닐아미노]-3-메톡시-벤조니트릴인 화합물.
  11. 평활근 수축 역효과 저하를 필요로 하는 환자에게 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염을 경구 또는 비경구적으로 투여함을 포함하여, 평활근 수축 역효과를 저하시키는 방법.
    상기 식에서, R1및 R2는 서로 독립적으로 수소, C1-10직쇄 알킬, C1-10측쇄 알킬 또는 C3-10사이클릭 또는 비사이클릭 알킬이고, A는
    로 이루어진 그룹(여기서, R3은 수소, C1-6알킬, C1-6퍼플루오로알킬, C1-6알콕시, C1-6퍼플루오로알콕시, 아미노, C1-6알킬아미노, C2-12디알킬아미노, C1-6알킬설폰아미도, C2-7알킬카복스아미도, 니트로, 시아노, 또는 카복실이다)으로부터 선택되거나, A는 일반식의 치환된 페닐 그룹(여기서, R4및 R5는 서로 독립적으로 시아노, 니트로, 아미노, C1-6알킬, C1-6퍼플루오로알킬, C1-6알콕시, C1-6퍼플루오로알콕시, 아미노, C1-6알킬아미노, C2-12디알킬아미노, 설파밀, C1-6설폰아미도, C6-12알킬설폰아미도, C2-7알킬카복스아미도, C7-13아릴카복스아미도, C1-6알킬설포닐, C1-6퍼플루오로알킬설포닐, C6-12아릴설포닐, 클로로, 브로모, 플루오로, 요오도, 1-이미다졸릴, 카복실 및 수소로 이루어진 그룹으로부터 선택되고, 단, R4및 R5는 동시에 수소일 수 없다)이다.
  12. 제10항에 있어서, 평활근 역 수축이 요실금을 야기시키는 방법.
  13. 제10항에 있어서, 평활근 역 수축이 과민성 장 증후군을 야기시키는 방법.
  14. 약제학적으로 허용되는 담체와의 배합물로 또는 약제학적으로 허용되는 담체와 함께 제1항 내지 제8항중의 어느 한 항에 따르는 화합물을 포함하는 약제학적 조성물.
  15. 일반식(Ⅱa)의 화합물을 일반식(Ⅳ)의 화합물과 반응시키고, 경우에 따라 A1을 A로 전환시키거나, Ra1을 R1으로 전환시키거나 Ra2를 R2로 전환시키고, 경우에 따라, 일반식(Ⅰ)의 화합물을 이의 약제학적으로 허용되는 염으로 전환시키거나, 일반식(Ⅰ)의 화합물의 염을 일반식(Ⅰ)의 화합물을 전환시킴을 포함하여 제1항에 따르는 화합물을 제조하는 방법.
    상기 식에서, A1은 제1항에서 정의한 A이거나, 이로 전환될 수 있는 원자의 그룹이고, X는 이탈 그룹이며, Ra1및 Ra2는 각각 제1항에서 정의한 R1및 R2이거나, 이로 전환될 수 있는 원자의 그룹이다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019960702542A 1993-11-17 1994-11-01 평활근 이완제로서의 디아미노사이클로부텐-3.4-디온(Diaminocyclobutene-3.4-diones as smooth muscle relaxants) KR960705780A (ko)

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US08/153,706 US5354763A (en) 1993-11-17 1993-11-17 Substituted N-heteroaryl and N-aryl-1,2-diaminocyclobutene-3,4-diones
US08/153,706 1993-11-17
PCT/US1994/012561 WO1995014005A1 (en) 1993-11-17 1994-11-01 Diaminocyclobutene-3,4-diones as smooth muscle relaxants

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Families Citing this family (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5466712A (en) * 1994-11-04 1995-11-14 American Home Products Corporation Substituted n-aryl-1,2-diaminocyclobutene-3,4-diones
ES2128774T3 (es) * 1994-11-16 1999-05-16 American Home Prod Diaminociclobuten-3,4-dionas.
US5464867A (en) * 1994-11-16 1995-11-07 American Home Products Corporation Diaminocyclobutene-3,4-diones
CN1227543A (zh) * 1996-06-17 1999-09-01 美国家用产品公司 作为钾通道调节剂的环丁烯－3,4－二酮的杂环甲基氨基衍生物
US5872139A (en) * 1996-06-17 1999-02-16 American Home Products Corporation Heterocyclymethylamino derivatives of cyclobutene-3,4-diones
US5750574A (en) * 1996-07-17 1998-05-12 American Home Products Corporation Fluorinated N-arylmethylamino derivatives of cyclobutene-3,4-diones
US5780505A (en) * 1996-07-17 1998-07-14 American Home Products Corporation Substituted N-arylmethylamino derivatives of cyclobutene-3, 4-diones
US5763474A (en) * 1996-07-17 1998-06-09 American Home Products Corporation Substituted N-arylmethylamino derivatives of cyclobutene-3,4-diones
US5846999A (en) * 1996-07-17 1998-12-08 American Home Products Corporation Substituted N-arylmethylamino derivatives of cyclobutene-3,4-diones
AU6250298A (en) * 1997-01-30 1998-08-25 American Home Products Corporation Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones
US5840764A (en) * 1997-01-30 1998-11-24 American Home Products Corporation Substituted hydroxy-anilino derivatives of cyclobutene-3,4-diones
US6376555B1 (en) 1998-12-04 2002-04-23 American Home Products Corporation 4-substituted-3-substituted-amino-cyclobut-3-ene-1,2-diones and analogs thereof as novel potassium channel openers
EP1135365A1 (en) * 1998-12-04 2001-09-26 American Home Products Corporation 4-3-substituted-amino-cyclobut-3-ene-1,2-diones and use for influencing smooth muscle contraction
AU6019900A (en) * 1999-11-24 2001-06-04 Sumika Fine Chemicals Co., Ltd. Anhydrous mirtazapine crystals and process for producing the same
US20030204085A1 (en) * 2001-02-02 2003-10-30 Taveras Arthur G. 3, 4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor antagonists
US6495576B2 (en) 2001-02-07 2002-12-17 Abbott Laboratories Aminal diones as potassium channel openers
MY149050A (en) * 2001-04-16 2013-07-15 Merck Sharp & Dohme 3,4 di-substituted cyclobutene-1,2-diones as cxc-chemokine receptor ligands
US20040106794A1 (en) * 2001-04-16 2004-06-03 Schering Corporation 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
US7132445B2 (en) * 2001-04-16 2006-11-07 Schering Corporation 3,4-Di-substituted cyclobutene-1,2-diones as CXC-chemokine receptor ligands
EP1434775A1 (en) * 2001-10-12 2004-07-07 Schering Corporation 3,4-di-substituted maleimide compounds as cxc-chemokine receptor antagonists
US6878709B2 (en) * 2002-01-04 2005-04-12 Schering Corporation 3,4-di-substituted pyridazinediones as CXC chemokine receptor antagonists
WO2003080053A1 (en) * 2002-03-18 2003-10-02 Schering Corporation Combination treatments for chemokine-mediated diseases
CN1720240B (zh) * 2002-10-09 2010-10-27 先灵公司 作为cxc-和cc-趋化因子受体配体的噻二唑二氧化物和噻二唑氧化物
CN1918138B (zh) * 2003-12-19 2011-05-04 先灵公司 作为cxc-和cc-趋化因子受体配体的噻二唑化合物
MXPA06007205A (es) * 2003-12-22 2006-08-31 Schering Corp Dioxidos de isotiazol como ligandos del receptor cxc y cc-quimiocina.
DE602004021404D1 (de) 2004-12-23 2009-07-16 Gpc Biotech Ag Quadratsäurederivate mit antiproliferativer Wirkung
EP1907399B1 (en) * 2005-06-29 2010-10-27 Schering Corporation 5,6-di-substituted oxadiazolopyrazines and thiadiazolopyrazines as cxc-chemokine receptor ligands
JP2009500334A (ja) * 2005-06-29 2009-01-08 シェーリング コーポレイション Ｃｘｃ−ケモカインレセプターリガンドとしてのジ置換オキサジアゾール
US7956185B2 (en) * 2006-05-26 2011-06-07 Abbott Laboratories Cyclobut-3-ene-1,2,-dione inhibitors of polo-like kinases
MX2009000123A (es) * 2006-07-07 2009-03-25 Schering Corp Ciclobuten-1,2-dionas 3,4-di-sustituidas como ligandos del receptor de quimiocina-cxc.
US8450348B2 (en) 2007-02-21 2013-05-28 Forma Tm, Llc Derivatives of squaric acid with anti-proliferative activity
AU2009264273B2 (en) 2008-06-24 2015-01-22 Onxeo Dk, Branch Of Onxeo S.A., France Squaric acid derivatives as inhibitors of the nicotinamide
UA103198C2 (en) * 2008-08-04 2013-09-25 Новартис Аг Squaramide derivatives as cxcr2 antagonists
US9178235B2 (en) 2009-09-04 2015-11-03 Lg Fuel Cell Systems, Inc. Reducing gas generators and methods for generating a reducing gas
US9083020B2 (en) 2009-09-04 2015-07-14 Lg Fuel Cell Systems Inc. Reducing gas generators and methods for generating reducing gas
US8597841B2 (en) 2009-09-04 2013-12-03 Lg Fuel Cell Systems Inc. Method for generating a gas which may be used for startup and shutdown of a fuel cell
US9118048B2 (en) 2009-09-04 2015-08-25 Lg Fuel Cell Systems Inc. Engine systems and methods of operating an engine
US8668752B2 (en) * 2009-09-04 2014-03-11 Rolls-Royce Fuel Cell Systems (Us) Inc. Apparatus for generating a gas which may be used for startup and shutdown of a fuel cell
US9140220B2 (en) 2011-06-30 2015-09-22 Lg Fuel Cell Systems Inc. Engine systems and methods of operating an engine
US9874158B2 (en) 2009-09-04 2018-01-23 Lg Fuel Cell Systems, Inc Engine systems and methods of operating an engine
US8889730B2 (en) 2012-04-10 2014-11-18 Pfizer Inc. Indole and indazole compounds that activate AMPK
CA2905242C (en) 2013-03-15 2016-11-29 Pfizer Inc. Indole compounds that activate ampk
JP2020530848A (ja) 2017-08-14 2020-10-29 アラーガン、インコーポレイテッドＡｌｌｅｒｇａｎ，Ｉｎｃｏｒｐｏｒａｔｅｄ ３，４−二置換３−シクロブテン−１，２−ジオンおよびその使用
CN112672791B (zh) 2018-09-21 2023-10-03 辉瑞公司 用作ccr6抑制剂的n-取代二氧代环丁烯基氨基-3-羟基-吡啶甲酰胺

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4390701A (en) * 1981-05-18 1983-06-28 Bristol-Myers Company 1-Amino-2-[3-(3-piperidinomethylphenoxy)propylamino]cyclobutene-3,4-dione
JPS60255756A (ja) * 1984-06-01 1985-12-17 Ikeda Mohandou:Kk アミノアルキルフエノキシ誘導体
US5011837A (en) * 1988-08-09 1991-04-30 E. R. Squibb & Sons, Inc. Aryl cyanoguanidines: potassium channel activators and method of making same
DE68926729T2 (de) * 1988-09-16 1997-02-13 Beecham Group Plc Benzopyranderivate mit einer blutdrucksenkenden Wirkung
GB8924373D0 (en) * 1989-10-30 1989-12-20 Beecham Group Plc Novel compounds
US5212283A (en) * 1992-03-03 1993-05-18 The United States Of America As Represented By The Administrator Of The National Aeronautics And Space Administration Polyimides containing the cyclobutene-3, 4-dione moiety
JPH0692915A (ja) * 1992-07-28 1994-04-05 Sumitomo Metal Ind Ltd １，２−ジアミノシクロブテン−３，４−ジオン誘導体及びその用途

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