KR920006314A - 아릴알킬아민, 이의 제조방법 및 이를 함유하는 약제학적 조성물 - Google Patents

아릴알킬아민, 이의 제조방법 및 이를 함유하는 약제학적 조성물 Download PDF

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KR920006314A
KR920006314A KR1019910015523A KR910015523A KR920006314A KR 920006314 A KR920006314 A KR 920006314A KR 1019910015523 A KR1019910015523 A KR 1019910015523A KR 910015523 A KR910015523 A KR 910015523A KR 920006314 A KR920006314 A KR 920006314A
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에몽-알트 자비에르
굴라우익 삐에르
프로이에또 빈센조
반 브뢰크 디디에르
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알링 시. 세워드
사노피
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Abstract

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아릴알킬아민, 이의 제조방법 및 이를 함유하는 약제학적 조성물
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Claims (13)

  1. 하기 일반식(1)의 화합물 또는 그의 무기산 또는 유기산과의 염.
    상식에서, -Y는·Cy-N의기[식중, Cy는 수소, 할로겐원자, 히드록실 C1∼C4알콕시, C1∼C4알킬, 트리플루오메틸 중에서 선택된 동일하거나 상이한 치환체 중의 하나로 한번 이상 치환된 페닐 또는 비치환된 페닐, C3∼C7시클로알킬기, 피리미디닐기 또는 피리딜기이다]이거나,의기[식중, Ar은 수소, 할로겐원자, 히드록실, C1∼C4알콕시, 트리플루오로메틸, C1∼C4알킬 중에서 선택된 동일하거나 상이한 치환체 중의 하나로 한번 이상 치환된 페닐 또는 피치환된 페닐, 피리딜기, 티에닐기이고, X는 0또는 1이며, X는 히드록실, C1∼C4알킬렌이 C1∼C3인 아미노알킬렌, -N-(X1)2의 기(여기서, X1기는 각각 수소, C1∼C4알킬이다),AIK의 기(여기서, AIK는 C1∼C6알킬이다),의기(여기서, AIK1은 C1∼C3알킬렌이고, AIK1'는 C1∼C3알킬이다), C1∼C4아실, -S-X2의기(여기서, X2는 수소 또는 C1∼C4알킬기이다), 또는 X는 X가 결합된 탄소원자 및 헤테로고리내에서 인접한 탄소원자와 함께 이중결합을 형성하다]이고, -m은 2 또는 3이며, -Ar'는 수소, 할로겐 원자, 바람직하게는 염소 또는 불소원자, 트리플로우로메틸, C1∼C4알콕시, C1∼C4알킬 중에서 선택된 동일하거나 상이한 치환체중의 하나로 한번 이상 치환된 페닐 또는 비치환된 페닐, 티에닐, 벤조티에닐, 나프틸, 인돌릴, C1∼C3알킬로 N-치환된 인돌릴이고, -R은 수소, C1∼C6알킬이며, -T는중에서 선택된 기(식중, W는 산소 또는 황원자이다)이고, -Z는 수소이거나, T가의 기일 경우 M 또는 OM이거나, T가의 기일 경우 M(여기서, M은 C1∼C6알킬, 방향족 고리에 할로겐, 트리플루오로메틸, C1∼C4알킬, 히드록실, C1∼C4알콕시가 임의 치환되었으며 알킬이 C1∼C3기인 페닐알킬, 알킬이 C1∼C3기인 피리딜알킬, 니프틸고리계에 할로겐, 트리플루오로메틸, C1∼C4알킬, 히드록실, C1∼C4알콕시가 임의 치환되었으며, 알킬이 C1∼C3기인 나프틸알킬, 알킬이 C1∼C3기인 피리딜 티오알킬, 스티릴, 임의 치환된 일-, 이- 또는 삼원 방향족 또는 헤테로방향족기이다.]
  2. 제1항에 있어서, Ar'가 3,4-디클로로페닐기인 화합물 또는 그의 무기산 또는 유기산과의 염.
  3. 제1항 또는 제2항에 있어서, X가 히드록실, 아세틸옥시 또는 일반식(여기서, AIK는 C1∼C6알킬이다)인 화합물 또는 그의 무기산 또는 유기산과의 염.
  4. 제1항 내지 제3항중 어느 한 항에 있어서, R이 메틸인 화합물 또는 그의 무기산 또는 유기산과의 염.
  5. 제1항 내지 제4항중 어느 한 항에 있어서, T가 -C=0 기 인 화합물 또는 그의 무기산 또는 유기산과의 염.
  6. 제1항 내지 제5항중 어느 한 항에 있어서, T가 -C=0기이고 Z가 티에닐기인 화합물 또는 그의 무기산 또는 유기산과의 염.
  7. 제1항 내지 제5항중 어느 한 항에 있어서, T가 -C=0 기이고 Z가 염소와 같은 할로겐으로 이치환 될수 있는 페닐기인 화합물 또는 그의 무기산 또는 유기산과의 염.
  8. 제1항에 내지 제7항중 어느 한 항에 있어서, 라세미형 또는 거울상 이성질체형의 N-메틸-N-[4-(4-페닐-4-아세틸아미노피페리딜)-2-(3,4-디클로로페닐)부틸]벤즈아미드 및 그의 무기산 또는 유기산과의 염.
  9. (-)-N-메틸-N-[4-(4-페닐-4-아세틸 아미노피페리딜-2-(3,4-디클로로페닐)부틸]벤즈아미드 및 그의 무기산 또는 유기산과의 염.
  10. (+)-N-메틸-N-[4-(4-페닐-4-아세틸 아미노피페리딜-2-(3,4-디클로로페닐)부틸]벤즈아미드 및 그의 무기산 또는 유기산과의 염.
  11. 하기한 바를 특징으로 하는 제1항 내지 제7항에 따른 화합물의 제조방법. -a)광학적으로 순수한 형태일 수 있는 하기 일반식(Ⅱ) 또는 (Ⅱ'")의 유리 아민을, T가 -CO-인 일반식(Ⅰ)의 화합물을 제조하는 경우 하기 일반식(Ⅲ)의 산의 관능 유도체로 처리하거나 또는 T가 -C(W)-NH-인 일반식(Ⅰ)의 화합물을 제조하는 경우 하기 일반식(Ⅲ')의 이소(티오)시아네이트로 처리하여 하기 일반식(Ⅳ)의 화합물을 형성하고,
    [상기식에서, m, Ar', R, Z 및 W는 제1항에서 정의한 바와같고, E는 예를들면, 테트라히드로-2-피라닐 옥시 또는의기(여기서, Y는 제1항에서 정의한 바와같고 X가 히드록실일때, 이 히드록실기는 보호될 수 있다)와 같은 O-보호기이다.]-b)E가 테트라히드로피라닉옥시기인 경우, 산을 작용시켜 테트라히드로피라닐 기를 제거하며, 이 탈보호는 일반식 (Ⅱ'")의 화합물을 수득하기 위하여 임의적으로 일반식(Ⅱ)의 화합물 상에서 직접 행한 후 일반식(Ⅱ)의 화합물 상에서 직접 행한후 일반식(Ⅲ) 또는 (Ⅲ')의 화합물로 처리하고, c)수득한 하기 일반식(Ⅴ)의 N-치환 알칸올아민을 메탄술포닐 클로라이드로 처리하며,
    d)수득한 하기 일반식(Ⅵ)의 메실레이트를 하기 일반식(Ⅶ)의 2급 아민으로 처리하고,
    (식중, Y는 제1항에서 정의한 바와같다) e) 적당하다면, X로 나타내는 히드록실을 탈보호시킨 후, 수득한 생성물을 그의 염으로 임의로 전환시킨다,
  12. 제1항 내지 제7항중 어느 한 항에 따른 일반식(Ⅰ)의 화합물을 유효성분으로서 함유하는 약제학적 조성물.
  13. 제12항에 있어서, 활성 성분을 하나 이상의 약제학적 부형제와 혼합한 복용단위인 약제학적 조성물.
    ※ 참고사항 : 최초출원 내용에 의하여 공개되는 것임.
KR1019910015523A 1990-09-05 1991-09-05 아릴알킬아민, 이의 제조방법 및 이를 함유하는 약제학적 조성물 KR100194823B1 (ko)

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Families Citing this family (117)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6218364B1 (en) 1988-06-20 2001-04-17 Scott L. Harbeson Fluorinated neurokinin A antagonists
US5830863A (en) * 1988-06-20 1998-11-03 Merrell Pharmaceuticals Inc. Neurokinin A antagonists
AU638264B2 (en) * 1989-08-10 1993-06-24 Aventis Inc. Cyclic neurokinin a antagonists
FR2676053B1 (fr) * 1991-05-03 1993-08-27 Sanofi Elf Nouveaux composes dialkylenepiperidino et leurs enantiomeres, procede pour leur preparation et compositions pharmaceutiques les contenant.
GB9201179D0 (en) * 1992-01-21 1992-03-11 Glaxo Group Ltd Chemical compounds
FR2688219B1 (fr) * 1992-03-03 1994-07-08 Sanofi Elf Sels d'ammonium quaternaires de composes aromatiques amines, leur preparation et compositions pharmaceutiques les contenant.
FR2688218A1 (fr) * 1992-03-03 1993-09-10 Sanofi Elf Sels d'ammonium quaternaires de composes aromatiques amines, leur preparation et compositions pharmaceutiques les contenant.
US5391819A (en) * 1992-09-30 1995-02-21 Merck & Co., Inc. Process of making chiral 2-aryl-1,4-butanediamine derivatives as useful neurokinin-A antagonists
FR2696178B1 (fr) * 1992-09-30 1994-12-30 Sanofi Elf Amides basiques quaternaires, procédé pour leur préparation et compositions pharmaceutiques en contenant.
US5583134A (en) * 1992-09-30 1996-12-10 Sanofi 1-azoniabicyclo[2.2.2] octanes and pharmaceutical compositions in which they are present
GB9321557D0 (en) * 1992-11-03 1993-12-08 Zeneca Ltd Carboxamide derivatives
FR2700472B1 (fr) * 1993-01-19 1995-02-17 Rhone Poulenc Rorer Sa Association synergisante ayant un effet antagoniste des récepteurs NK1 et NK2.
US5869496A (en) * 1993-01-28 1999-02-09 Merck & Co., Inc. Spiro-substituted azacycles as tachykinin receptor antagonists
US5512680A (en) * 1993-02-26 1996-04-30 Sanofi Process for the preparation of an optically pure aminoalcohol
US5635510A (en) * 1993-05-06 1997-06-03 Merrell Pharmaceuticals Inc. Substituted pyrrolidin-3-yl-alkyl-piperidines
CN1081635C (zh) * 1993-05-06 2002-03-27 默里尔药物公司 取代的吡咯烷 -3-基-烷基-哌啶
GB9310066D0 (en) * 1993-05-17 1993-06-30 Zeneca Ltd Alkyl substituted heterocycles
GB9310713D0 (en) * 1993-05-24 1993-07-07 Zeneca Ltd Aryl substituted heterocycles
GB9317104D0 (en) * 1993-08-17 1993-09-29 Zeneca Ltd Therapeutic heterocycles
WO1995011880A1 (en) * 1993-10-27 1995-05-04 Merck Sharp & Dohme Limited Substituted amides as tachykinin antagonists
GB9322643D0 (en) * 1993-11-03 1993-12-22 Zeneca Ltd Lactam derivatives
US6869957B1 (en) 1993-11-17 2005-03-22 Eli Lilly And Company Non-peptide tachykinin receptor antagonists
US6403577B1 (en) * 1993-11-17 2002-06-11 Eli Lilly And Company Hexamethyleneiminyl tachykinin receptor antagonists
GB9325074D0 (en) * 1993-12-07 1994-02-02 Zeneca Ltd Bicyclic heterocycles
US5589489A (en) * 1993-12-15 1996-12-31 Zeneca Limited Cyclic amide derivatives for treating asthma
EP0739336B1 (en) * 1994-01-13 1998-08-26 MERCK SHARP & DOHME LTD. Gem-disubstituted azacyclic tachykinin antagonists
GB2287404A (en) * 1994-03-15 1995-09-20 Pfizer Antiinflammatory and analgesic compositions
FR2717477B1 (fr) * 1994-03-18 1996-06-07 Sanofi Elf Composés antagonistes sélectifs du récepteur NK3 humain et leur utilisation comme médicaments et outils de diagnostic.
FR2719311B1 (fr) * 1994-03-18 1998-06-26 Sanofi Sa Composés antagonistes sélectifs du récepteur NK3 humain et leur utilisation comme médicaments et outils de diagnostic.
FR2717478B1 (fr) * 1994-03-18 1996-06-21 Sanofi Sa Composés antagonistes sélectifs du récepteur NK3 humain et leur utilisation comme médicaments et outils de diagnostic.
FR2717802B1 (fr) * 1994-03-25 1996-06-21 Sanofi Sa Nouveaux composés aromatiques, procédé pour leur préparation et compositions pharmaceutiques en contenant.
FR2718136B1 (fr) * 1994-03-29 1996-06-21 Sanofi Sa Composés aromatiques aminés, procédé pour leur obtention et compositions pharmaceutiques les contenant.
US5434158A (en) * 1994-04-26 1995-07-18 Merck & Co., Inc. Spiro-substituted azacycles as neurokinin-3 antagonists
GB9408872D0 (en) * 1994-05-03 1994-06-22 Zeneca Ltd Heterocyclic compounds
BR9508375A (pt) * 1994-07-12 1997-10-28 Lilly Co Eli Antagonista de receptor de taquicinina heterociclica
AU3162695A (en) * 1994-08-03 1996-03-04 Asta Medica Aktiengesellschaft Indol, indazol, pyridopyrrol and pyridopyrazol derivatives with anti-asthmatic, anti-allergic, anti-inflammatory and immunomodulating effects
TW432061B (en) * 1994-08-09 2001-05-01 Pfizer Res & Dev Lactams
ES2132709T3 (es) 1994-08-25 1999-08-16 Merrell Pharma Inc Nuevas piperidinas substituidas utiles para el tratamiento de las enfermedades alergicas.
US5607936A (en) * 1994-09-30 1997-03-04 Merck & Co., Inc. Substituted aryl piperazines as neurokinin antagonists
US5998444A (en) * 1995-10-24 1999-12-07 Zeneca Ltd. Piperidinyl compounds as NK1 or NK2 antagonists
DE69534213T2 (de) * 1994-10-25 2006-01-12 Astrazeneca Ab Therapeutisch wirksame Heterocyclen
US6008223A (en) * 1994-10-27 1999-12-28 Zeneca Limited Therapeutic compounds
GB9421709D0 (en) * 1994-10-27 1994-12-14 Zeneca Ltd Therapeutic compounds
CA2162786A1 (en) * 1994-11-22 1996-05-23 Philip Arthur Hipskind Heterocyclic tachykinin receptor antagonists
FR2729952B1 (fr) * 1995-01-30 1997-04-18 Sanofi Sa Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant
FR2729954B1 (fr) * 1995-01-30 1997-08-01 Sanofi Sa Composes heterocycliques substitues, procede pour leur preparation et compositions pharmaceutiques les contenant
GB9505084D0 (en) * 1995-03-14 1995-05-03 Pfizer Ltd Benzamide derivative
EP0815105B1 (en) * 1995-03-15 2001-10-04 Aventis Pharmaceuticals Inc. Heterocyclic substituted piperazinone derivatives as tachykinin receptor antagonists
US6294537B1 (en) * 1995-03-17 2001-09-25 Sanofi-Synthelabo Compounds which are specific antagonists of the human NK3 receptor and their use as medicinal products and diagnostic tools
DE69633442T2 (de) * 1995-04-13 2006-01-05 Aventis Pharmaceuticals Inc. Neue substituierte piperazinderivate mit tachykininrezeptor-antagonistischer wirkung
US5716970A (en) * 1995-04-27 1998-02-10 Pharmacia & Upjohn Company Diuretic compound
GB9508786D0 (en) 1995-04-29 1995-06-21 Zeneca Ltd Substituted heterocycles
US5719156A (en) * 1995-05-02 1998-02-17 Schering Corporation Piperazino derivatives as neurokinin antagonists
US5696267A (en) * 1995-05-02 1997-12-09 Schering Corporation Substituted oximes, hydrazones and olefins as neurokinin antagonists
US5795894A (en) * 1995-05-02 1998-08-18 Schering Corporation Piperazino derivatives as neurokinn antagonists
US5688960A (en) * 1995-05-02 1997-11-18 Schering Corporation Substituted oximes, hydrazones and olefins useful as neurokinin antagonists
DE69626123T2 (de) * 1995-06-06 2003-10-09 Schering Corp Substituierte benzokondensierte heterocyclen als neurokinin antagonisten
US5654316A (en) * 1995-06-06 1997-08-05 Schering Corporation Piperidine derivatives as neurokinin antagonists
FR2738245B1 (fr) * 1995-08-28 1997-11-21 Sanofi Sa Nouveaux derives de piperidine, procede pour leur obtention et compositions pharmaceutiques les contenant
US5892039A (en) * 1995-08-31 1999-04-06 Schering Corporation Piperazino derivatives as neurokinin antagonists
FR2738819B1 (fr) * 1995-09-14 1997-12-05 Sanofi Sa Nouveaux composes antagonistes selectifs du recepteur nk3 humain, procede pour leur obtention et compositions pharmaceutiques les contenant
GB9523526D0 (en) * 1995-11-17 1996-01-17 Zeneca Ltd Therapeutic compounds
US6211199B1 (en) 1995-11-17 2001-04-03 Aventis Pharmaceuticals Inc. Substituted 4-(1H-benzimidazol-2-yl-amino)piperidines useful for the treatment of allergic diseases
RU2135494C1 (ru) 1995-12-01 1999-08-27 Санкио Компани Лимитед Гетероциклические соединения и композиция на их основе, проявляющая антагонистическое действие в отношении рецепторов тахикинина
US6423704B2 (en) 1995-12-20 2002-07-23 Aventis Pharmaceuticals Inc. Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic diseases
US6194406B1 (en) 1995-12-20 2001-02-27 Aventis Pharmaceuticals Inc. Substituted 4-(1H-benzimidazol-2-yl)[1,4]diazepanes useful for the treatment of allergic disease
US5998439A (en) * 1996-02-21 1999-12-07 Hoescht Marion Roussel, Inc. Substituted N-methyl-N-(4-(piperidin-1-yl)-2-(aryl)butyl)benzamides useful for the treatment of allergic diseases
CN1096460C (zh) * 1996-02-21 2002-12-18 阿温蒂斯药物公司 用于治疗过敏性疾病的新的取代的n-甲基-n-(4-(哌啶-1-基)-2-(芳基)丁基)苯甲酰胺
US5922737A (en) * 1996-02-21 1999-07-13 Hoechst Marion Roussel, Inc. Substituted N-methyl-N-(4-(4-(1H-Benzimidazol-2-YL-amino) piperidin-1-YL)-2-(arlyl) butyl) benzamides useful for the treatment of allergic diseases
US5932571A (en) * 1996-02-21 1999-08-03 Hoechst Marion Roussel, Inc. Substituted N-methyl-N-(4-(4-(1H-benzimidazol-2-yl) {1,4}diazepan-1-yl)-2-(aryl) butyl) benzamides useful for the treatment of allergic diseases
CN1143856C (zh) * 1996-02-21 2004-03-31 阿温蒂斯药物公司 可用于治疗过敏性疾病的新的取代的 n-甲基 - n - ( 4 - ( 4 - ( 1 h-苯并咪唑 - 2 -基 ) [ 1 , 4 ]二氮杂环庚烷-1-基)-2-(芳基)丁基)苯甲酰胺类化合物
US5869488A (en) * 1996-05-01 1999-02-09 Schering Corporation Piperazino derivatives as neurokinin antagonists
US5691362A (en) * 1996-06-05 1997-11-25 Schering-Plough Corporation Substituted benzene-fused hetero- and carbocyclics as nuerokinin antagonists
WO1998018761A1 (en) * 1996-10-28 1998-05-07 Schering Corporation Substituted arylalkylamines as neurokinin antagonists
US5789422A (en) * 1996-10-28 1998-08-04 Schering Corporation Substituted arylalkylamines as neurokinin antagonists
US5968929A (en) * 1996-10-30 1999-10-19 Schering Corporation Piperazino derivatives as neurokinin antagonists
US5945428A (en) * 1996-11-01 1999-08-31 Schering Corporation Substituted oximes, hydrazones and olefins as neurokinin antagonists
US5977139A (en) * 1996-12-15 1999-11-02 Hoechst Marion Roussel, Inc. Carboxysubstituted cyclic carboxamide derivatives
US5861417A (en) * 1996-12-19 1999-01-19 Hoechst Marion Roussel, Inc. Heterocyclic substituted pyrrolidine amide derivatives
US6124319A (en) * 1997-01-21 2000-09-26 Merck & Co., Inc. 3,3-disubstituted piperidines as modulators of chemokine receptor activity
JP2001508798A (ja) * 1997-01-21 2001-07-03 メルク エンド カンパニー インコーポレーテッド ケモカインレセプター活性のモジュレーターとしての3,3−二置換ピペリジン類
SK7602000A3 (en) * 1997-11-21 2001-01-18 Schering Corp Substituted oximes as neurokinin antagonists
US6013652A (en) * 1997-12-04 2000-01-11 Merck & Co., Inc. Spiro-substituted azacycles as neurokinin antagonists
US6316445B1 (en) 1998-05-15 2001-11-13 Aventis Pharmaceuticals Inc. Carboxy substituted acylic carboxamide derivatives
FR2779429B1 (fr) * 1998-06-03 2000-07-13 Synthelabo Derives d'oxindole, leurs preparations et leurs applications en therapeutique
CN1309638A (zh) 1998-07-10 2001-08-22 阿斯特拉曾尼卡有限公司 作为神经激肽受体拮抗剂的n-取代的萘甲酰胺
GB9922521D0 (en) * 1998-10-07 1999-11-24 Zeneca Ltd Compounds
GB9922519D0 (en) 1998-10-07 1999-11-24 Zeneca Ltd Compounds
FR2784377B3 (fr) * 1998-10-09 2000-11-17 Sanofi Sa Nouveaux composes derives d'ureidopiperidine, antagonistes selectifs des recepteurs nk3 humains, procede pour leur obtention et compositions pharmaceutiques les contenant
US6063926A (en) * 1998-11-18 2000-05-16 Schering Corporation Substituted oximes as neurokinin antagonists
GB9826941D0 (en) * 1998-12-09 1999-02-03 Zeneca Pharmaceuticals Compounds
WO2000035918A1 (fr) * 1998-12-16 2000-06-22 Nippon Kayaku Kabushiki Kaisha Procedes de preparation de nouveaux derives de naphtyridine
CA2346933A1 (en) * 1998-12-18 2000-06-22 Dupont Pharmaceuticals Company N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
US6605623B1 (en) * 1998-12-18 2003-08-12 Bristol-Myers Squibb Pharma Co. N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
CA2350730A1 (en) * 1998-12-18 2000-06-22 George V. Delucca N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
US6486180B1 (en) 1998-12-18 2002-11-26 Bristol-Myers Squibb Pharma Company N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
US6331541B1 (en) 1998-12-18 2001-12-18 Soo S. Ko N-ureidoalkyl-piperidines as modulators of chemokine receptor activity
FR2792835B3 (fr) * 1999-04-27 2001-05-25 Sanofi Sa Utilisation du saredutant pour la preparation de medicaments utiles dans le traitement ou la prevention de l'ensemble des troubles de l'humeur, des troubles de l'adaptation ou des troubles mixtes anxiete-depression
WO2001047910A1 (fr) * 1999-12-24 2001-07-05 Mitsubishi Rayon Co., Ltd. Procede de preparation de tetrahydropyranyloxyamines
CN1440402A (zh) 2000-06-30 2003-09-03 布里斯托尔-迈尔斯斯奎布公司 作为趋化因子受体活性调节剂的n-脲基杂环烷基-哌啶
US6511994B2 (en) * 2000-10-11 2003-01-28 Merck & Co., Inc. Modulators of CCR5 chemokine receptor activity
EP1370520A1 (en) 2001-03-21 2003-12-17 Pharmacopeia, Inc. Aryl and biaryl compounds having mch modulatory activity
PE20021081A1 (es) 2001-04-12 2002-12-18 Pharmacopeia Drug Discovery Aril y biaril piperidinas con actividad moduladora mch
AU2002259147A1 (en) 2001-05-08 2002-11-18 Schering Corporation Use of neurokinin receptor antagonists to treat androgen-dependent diseases
DE60217363T2 (de) 2001-09-06 2007-10-11 Schering Corp. 17beta-hydroxysteroid dehydrogenase type 3 inhibitoren zur behandlung von androgen-abhängigen erkrankungen
DZ3292A1 (fr) 2001-09-13 2005-05-14 Solvay Pharm Gmbh Nouveaux composes de type 1-[1-(hetero)aryl-1-perhydroxyalkylmethyl]piperazine, methodes pour les preparer et medicaments renfermant cescomposes
ATE471315T1 (de) * 2001-10-17 2010-07-15 Schering Corp Piperidin- und piperazinacetamide als inhibitoren der 17beta-hydroxysteroiddehydrogenase des typs 3 zur behandlung androgenabhängiger krankheiten
CA2535646C (en) 2003-08-15 2010-08-10 H. Lundbeck A/S Cyclopropyl derivatives as nk3 receptor antagonists
CN102659774A (zh) 2005-08-15 2012-09-12 弗·哈夫曼-拉罗切有限公司 作为p2x3拮抗剂的哌啶和哌嗪衍生物
US7592344B2 (en) * 2005-11-30 2009-09-22 Solvay Pharmaceuticals Gmbh NK1 and NK2-antagonists and compositions and methods of using the same
FR2912057B1 (fr) * 2007-02-07 2009-04-17 Sanofi Aventis Sa Composition pharmaceutique contenant en association le saredutant et un inhibiteur selectif de la recapture de la serotonine ou un inhibiteur de la recapture de la serotonine/norepinephrine
WO2007136323A1 (en) * 2006-05-18 2007-11-29 Albireo Ab A novel process suitable for large-scale production of phenyl propan derivatives of formula i
TW200817003A (en) * 2006-07-31 2008-04-16 Sanofi Aventis Pharmaceutical composition comprising, in combination, saredutant and a selective serotonin peuptake inhibitor or a serotonin/norepinephrine reuptake inhibitor
US20090076083A1 (en) * 2007-09-19 2009-03-19 Protia, Llc Deuterium-enriched saredutant
CZ301920B6 (cs) * 2009-06-16 2010-07-28 Zentiva, K. S. Zpusob výroby (S)-4-methylamino-3-(3,4-dichlorfenyl)butan-1-olu
WO2016100940A1 (en) 2014-12-19 2016-06-23 The Broad Institute, Inc. Dopamine d2 receptor ligands
EP3233799B1 (en) 2014-12-19 2021-05-19 The Broad Institute, Inc. Dopamine d2 receptor ligands

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL254248A (ko) * 1959-07-29
NL6710477A (ko) * 1966-07-29 1968-01-30
US4145435A (en) * 1976-11-12 1979-03-20 The Upjohn Company 2-aminocycloaliphatic amide compounds
AT376669B (de) * 1982-11-26 1984-12-27 Laevosan Gmbh & Co Kg Verfahren zur herstellung neuer thienylessigsaeureamid-derivate und pharmazeutisch vertraeglicher saeureadditionssalze davon
ZA842753B (en) * 1983-05-18 1984-11-28 Upjohn Co 2-dihydropyrrolyl-cycloalkyl-amide analgesics
US4920116A (en) * 1985-06-28 1990-04-24 Schering A.G. N-(aminoalkyl)-substituted(N or C alkyl)-aryl-4(methylsulfonylamino)benzamides
US4751327A (en) * 1985-06-28 1988-06-14 Xerox Corporation Photoconductive imaging members with unsymmetrical squaraine compounds
GB8618188D0 (en) * 1986-07-25 1986-09-03 Ici Plc Diamine compounds
DE3766335D1 (de) * 1986-09-17 1991-01-03 Zambeletti Spa L N-1-acylierte-(1-(phenyl- oder benzyl-))-1,2-aethylendiamine.
FR2613719B1 (fr) * 1987-04-10 1991-03-22 Sanofi Sa Derives aromatiques, leur preparation et leur utilisation comme antimicrobiens
GB8801304D0 (en) * 1988-01-21 1988-02-17 Ici Plc Diamine compounds
IE903957A1 (en) * 1989-11-06 1991-05-08 Sanofi Sa Aromatic amine compounds, their method of preparation and¹pharmaceutical compositions in which they are present

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IE913082A1 (en) 1992-03-11
NO913469D0 (no) 1991-09-04
RU2070196C1 (ru) 1996-12-10
ATE174332T1 (de) 1998-12-15
JPH04261155A (ja) 1992-09-17
HU222351B1 (hu) 2003-06-28
CA2050639A1 (en) 1992-03-06
FI98457C (fi) 1997-06-25
HU211893A9 (en) 1995-12-28
IL99320A0 (en) 1992-07-15
PL167994B1 (pl) 1995-12-30
AU657272B2 (en) 1995-03-09
LV10606A (lv) 1995-04-20
NO913469L (no) 1992-03-06
DE69130597D1 (de) 1999-01-21
FI914174A (fi) 1992-03-06
CA2050639C (en) 1997-12-02
SG47703A1 (en) 1998-04-17
MY142065A (en) 2010-08-30
US5350852A (en) 1994-09-27
EP0474561A1 (fr) 1992-03-11
IL99320A (en) 1995-07-31
GR3029435T3 (en) 1999-05-28
HK1005290A1 (en) 1998-12-31
PT98849A (pt) 1992-07-31
LV10606B (en) 1996-04-20
FI914174A0 (fi) 1991-09-04
NO177226C (no) 1995-08-09
KR100194823B1 (ko) 1999-06-15
NO177226B (no) 1995-05-02
ES2127722T3 (es) 1999-05-01
PL291618A1 (en) 1992-08-24
JP2620435B2 (ja) 1997-06-11
CS272491A3 (en) 1992-03-18
DK0474561T3 (da) 1999-08-16
DE69130597T2 (de) 1999-05-20
UA27224C2 (uk) 2000-08-15
FI98457B (fi) 1997-03-14
HUT59098A (en) 1992-04-28
PT98849B (pt) 1999-02-26
CZ285994B6 (cs) 1999-12-15
EP0474561B1 (fr) 1998-12-09
US5236921A (en) 1993-08-17
BR9103802A (pt) 1992-05-19
AU8354291A (en) 1992-03-12
NZ239661A (en) 1994-06-27

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