KR920002562A - 구아니딘 - Google Patents

구아니딘 Download PDF

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KR920002562A
KR920002562A KR1019910011300A KR910011300A KR920002562A KR 920002562 A KR920002562 A KR 920002562A KR 1019910011300 A KR1019910011300 A KR 1019910011300A KR 910011300 A KR910011300 A KR 910011300A KR 920002562 A KR920002562 A KR 920002562A
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guanidine
group
amidino
ethylene
piperidinylmethyl
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KR1019910011300A
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KR100218600B1 (ko
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애커만 쟝
반너 데이비드
구베르나토르 클라우스
해드베리 폴
힐페르트 쿠르트
뮐러 클라우스
라블레르 루드빅
슈미트 게르아르트
비. 쵸프 토마스
페터 베셀 한스
비르쯔 비트
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쟝-자크 오게이, 롤란드 보러
에프. 호프만-라 롯슈 아크티엔게젤샤프트
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    • C07C279/12—Derivatives of guanidine, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of guanidine groups bound to acyclic carbon atoms of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
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    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
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    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
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Abstract

내용 없음

Description

구아니딘
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (20)

  1. 하기 일반식(Ⅰ)의 구아니딘, 및 그의 수화물 또는 용매화물 및 생리학적으로 유용한 염.
    상기식에서, R은 아릴, 헤테로아릴 또는 헤테로사이클릴이고, T는 CH2또는 O이며, L은 NH 또는 O이고, -N(X)-M-은 -N-(SO2-R°)-CH2-그룹 또는 페닐환이 임의로 치환된 이소퀴놀릴렌 그룹이며, R°는 R과 동일한 의미를 갖거나, 또는 X가 H, -CH2COOH, -CH2COO-C1-4-알킬, -CH2CO-(테트라-내지 헵타메틸렌이미노) 또는 임의로는 N-모노-또는 N-디-C1-4-알킬화된 -CH2CONH2이고,M은 R'-(CH2)1-2CH=, R'-COCH2CH=, R"-COCH2CH=, R'-(CO)1-2NHCH2CH=, 벤질-OCONHCH2CH=, -CH2〔R'-(CO)1-2NH〕CH-, -CH2(벤질-OCONH)CH-또는 -CH(CO-Q)CH2-그룹이며, R'는 아릴, 헤테로아릴, 사이클로알킬 또는 헤테로사이클릴이고, R"는 임의로는 옥소, -COO-C1-4-알킬, -(CH2)0-1OH, -(CH2)0-1OCO-C1-4-알킬 및 임의로 모노-또는 디-C1-4-알킬화된 카바모일로 이루어진 그룹중에서 선택된 2개 이하의 치환체로 가진 테트라-내지 헵타메틸리렌이미노이며, Q는 임의로 O 또는 S-원자에 의해 차단되고, 임의로는 C1-4알킬, COOH, -COO-C1-4알킬, -CH2OH 및 -CH2O-벤질로 이루어진 그룹중에서 선택된 2개 이하의 치환체로 치환된 벤질아미노 또는 테트라-내지 헵타 메틸렌이미노 그룹이다.
  2. 제1항에 있어서, 하기 일반식(ⅠA)를 갖는 구아니딘, 및 그의 수화물 또는 용매화물 및 생리학적으로 유용한 염.
    상기식에서 -N(X')-M'-는 페닐 환이 임의로 치환된 이소퀴놀릴렌 그룹이거나, 또는 X'가 H, -CH2COOH, -CH2COO-C1-4-알킬, -CH2CO-(테트라-내지 헵타메틸렌이미노) 또는 임의로는 N-모노-또는 N-디-C1-4-알킬화된 -CH2CONH2이고, M'는 R' -(CH2)1-2CH=, R' -COCH2CH= 또는 -CH(CO-Q')CH2-그룹이며, Q'는 벤질아미노, 모르폴리노 또는 테트라-내지 헵타메틸렌 이미노이고, R, R', L 및 T는 제1항에서 정의된 의미를 갖는다.
  3. 제2항에 있어서, X'가 H이며, R,M',L 및 T가 제2항에서 정의된 의미를 갖는 구아니딘.
  4. 제1항에 있어서, 하기 일반식(ⅠB)를 갖는 구아니딘.
    상기식에서, M"은 R"-COCH2CH=, R' -(CO)1-2NHCH2CH=, 벤질 -OCONHCH2CH=, -CH2〔R' -(CO)1-2NH〕CH-, -CH2(벤질-OCONH)CH- 또는 -CH(CO-Q")CH2-그룹이고, Q"는 임의로는 O 또는 S 원자에 의해 차단되고, C1-4-알킬, COOH, -COO-C1-4-알킬, -CH2OH 및 -CH2O-벤질로 이루어진 그룹중에서 선택된 2개 이하의 치환체에 의해 임의로 치환된 테트라-내지 헵타메틸렌이미노 그룹이며, R, R', R", L 및 T는 제1항에서 정의된 의미를 갖는다.
  5. 제1항에 있어서, R, L, T, M 또는 N(X)-M- 및 X가 제1항에서와 동일한 의미를 갖지만, 단, X가 H는 아닌 구아니딘.
  6. 제1항에 있어서, R이 아릴, 특히 나프릴, 하이드록시나프틸, 4-비페닐, 2-안트릴, 요오도페닐, 니트로페닐, 벤질옥시페닐, 디메톡시페닐, 4-메톡시-2,3,6-트리메틸레닐, 2,4,6-트리이소프로필페닐, 카복시페닐, 메톡시카보닐페닐, 벤질옥시나프틸, 페닐설포닐페닐, 헥사하이드로아제피노일페닐 또는 t-부틸 페닐인 구아니딘.
  7. 제1항에 있어서, R이 헤테로아릴, 특히 3-메틸-8-퀴놀릴, 5-(1-메틸-5-트리플루오로메틸피라졸-3-일)-2-티에닐 또는 벤조티에닐인 구아니딘.
  8. 제1항 또는 제2항에 있어서, R이 헤테로사이클릴, 특히 3-메틸-1,2,3,5-테트라하이드로-8-퀴놀릴인 구아니딘.
  9. 제1항에 있어서, -N(X)-M-이 이소퀴놀릴렌 또는 N-디메틸아미노나프틸설포닐-아미노메틸렌인 구아니딘.
  10. 제1항 또는 제2항에 있어서, X가 H 또는 -CH2COOH인 구아니딘.
  11. 제1항에 있어서, M이 R'-(CH2)1-2CH= 그룹, 특히 3-인돌릴에틸리덴, 2,3-디옥소-1-인돌리닐에틸리덴, 펜에틸리덴, 1,4-디옥소-5H-2,5-벤조디아제핀-5-일에틸리덴, (플루오로, 클로로, 요오도, 시아노, 니트로, 아미노, 카복시, C1-4알콕시카보닐 또는 하이드록시)-펜에틸리덴, 사이클로헥실프로필리덴, 데칼릴, 에틸리덴, 이미다졸릴에틸리덴, 티에닐에틸덴, (메틸, 브로모, 플루오로 또는 카복시메틸)-3-인돌릴에틸리덴, 나프틸에틸리덴, (에톡시카보닐카보닐아미노, 메톡시카보닐 에틸카보닐아미노, 벤질옥시카보닐에틸카보닐아미노, 에톡시카보닐아미노, 벤조일카보닐아미노, 카복시벤조일아미노, 메톡시에톡시아세트아미도, 아세트아미도, 카복시카보닐아미노, 카복시프로피오닐아미노, 톨릴설폰아미도, 요오드페닐설폰아미도, 카복시페닐설폰아미도 또는 에톡시카보닐메틸아미노)펜에틸리덴, 옥소벤즈옥사졸린에틸리덴 또는 5-브로모-또는 5-메틸-2,3-디옥소-1-인돌리닐에틸리덴인 구아니딘.
  12. 제1항에 있어서, M이 (R' 또는 R")COCH2CH= 그룹, 특히 헥사하이드로아제피노일에틸리덴, (메톡시카보닐 또는 카복시)-피롤리디노일에틸리덴, 3,4-디하이드로-2(1H)-이소퀴놀리노일에틸리덴, (니트로, 아미노, 요오도 또는 포름아미도벤조일에틸리덴, 모르폴리노에틸리덴, 헵타하이드로아조시노일에틸리덴, (에톡시카보닐, 아세톡시메틸, 디메틸카바모일, 이소부티릴옥시메틸 또는 부티릴옥시메틸)-피페리디노일에틸리덴, 3-메톡시카보닐-4-옥소피페리디노일에틸리덴 똔ㄴ 4-아세톡시-3-에톡시카보닐피페리디노일에틸리덴인 구아니딘.
  13. 제1항에 있어서, M이 R'-(CO)1-2NHCH2CH= 그룹, 특히 벤조일카복스아미도에틸리덴, 티에노일카복스아미도에틸리덴, 벤조일아미도에틸리덴 또는 벤질옥시카복스아미도에틸리덴인 구아니딘.
  14. 제1항에 있어서, M이 -CH2〔R'-(CO)1-2NH〕CH- 그룹, 특히 2-(카복시벤조일아미도)에틸렌, 2-(벤질옥시벤조일아미도)에틸렌, 2-(2-피페리딘카복스아미도)에틸렌, 2-(하이드록시벤조일아미도) 에틸렌 또는 2-(아미노벤조일아미도)에틸렌인 구아니딘.
  15. 제1항에 있어서, M이 -CH(CO-Q)CH2- 그룹, 특히 1-(벤질아미노카보닐)에틸렌, 1-(헥사하이드로아제피노일)에틸렌, 1-(모르폴리노일)에틸렌, 1-(헵타하이드로아조시노일)에틸렌, 1-〔2-(벤질옥시메틸모르폴리노일)〕에틸렌, 1-〔2-(하이드록시메틸모르폴리노일)〕에틸렌, 1-(2-에톡시카보닐-4-메틸피페리디노일)에틸렌, 1-(2-카복시-4-메틸피페리디노일)에틸렌 또는 1-(3-카복시헥사하이드로-1,4-옥스아제피노일)에틸렌인 구아니딘.
  16. 제1항, 제2항 또는 제6항에 있어서, R이 아릴, 특히 나프틸 또는 니트로-또는 요오도페닐이고, L이 NH이며, 피페리딘 또는 모르폴린 환내의 비대칭 C원자가 (S)- 배위를 갖는 구아니딘.
  17. 제1항, 제11항 또는 제12항에 있어서, 하기 일반식(ⅠC)를 갖는 구아니딘.
    상기식에서, A는 아릴, 아로일 또는 헤테로사이클릴, 특히 페닐, 니트로 페닐, 인돌릴, 2,3-디옥소-1-인돌리일 또는 아미노 벤조일이다.
  18. 제1항 또는 제2항에 있어서, 하기 화합물들로 이루어진 그룹으로부터 선택된 구아니딘, (R)-N-〔(RS)-1-아미디노-3-피페리디닐메틸〕-α-(2-나프틸설폰아미도)-2,3-디옥소-1-인돌린프로피온아미드, (R)-N-〔(RS)-1-아미디노-3-피페리디닐메틸〕-α-(2-나프틸설폰아미도)-o-니트로하이드로신아미드, (R)-N-〔(RS)-1-아미디노-3-피페리디닐메틸〕-α-(a-니트로벤젠설폰아미도)-인돌-3-프로피온아미드, (R)-N-〔(S)-1-아미디노-3-피페리디닐메틸〕-α-(p-요오도벤젠설폰아미도)-인돌-3-프로피온아미드, (R)-N-〔(S)-1-아미디노-3-피페리디닐메틸〕-α-(p-요오도벤젠설폰아미도)-p-니트로하이드로신남아미드, (R)-N-〔(RS)-1-아미디노-3-피페리디닐메틸〕-3-(o-아미노벤조일)-(2-나프틸설폰아미도)프로피온아미드, N-〔(R)-α-〔〔(S)-1-아미디노-3-피페리디닐〕메틸카바모일〕-펜에닐〕-N-(2-나프틸설포닐)글리신, (R)-N-〔(S)-1-아미디노-3-피페리디닐메틸〕-1,2,3,4-테트라하이드로-2-(2-나프틸설포닐)-3-이소퀴놀린카복스아미드, (S)-N-〔(RS)-1-아미디노-3-피페리디닐메틸〕-헥사하이드로-β-(2-나프틸설폰아미도)-γ-옥소-1H-1-아제핀부티르아미드, (R)-N-〔(S)-1-아미디노-3-피페리디닐메틸〕-α-(2-나프틸설폰아미도)-2,3-디옥소-1-인돌린프로피온아미드, 4'-〔(R)-2〔〔〔(S)-1아미디노-3-피페리디닐메틸〕메틸〕카바모임〕-2-(2-나프틸설폰아미드)에틸〕옥사닐산, (S)-N-〔(RS)-1-아미디노-3-피페리디닐메틸〕메닐〕-헥사하이드로-β-(2-나프틸설폰아미도)-γ-옥소-1(2H)-아조신부티르아미드, (2RS, 4R)-1-〔N4-〔〔(S)-1-아미디노-3-피페리디닐메틸〕메닐〕-N2-(2-니프틸설포닐)-L-아스파라기닐〕-4-메틸-2-피페리딘카복실산, 4'-〔(R)-2-〔〔〔(S)-1아미디노-3-피페리디닐〕메틸〕카바모일〕-2-(2-나프틸설폰아미도)에틸〕숙신아닐리드산.
  19. 제1항 내지 제18항중 어느 한항에 따른 화합물을 활성성분으로서 함유하는 약제학적 제제.
  20. 하기 일반식(Ⅲ),(Ⅳ) 및 (Ⅴ)의 화합물.
    상기식들에서, R, T, L, X 및 M은 제1항에서 정의된 바와 같다.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102271668B1 (ko) * 2021-01-22 2021-07-02 김기련 원자력 발전소 증기발생기 랜싱 프로세스장치

Families Citing this family (87)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
TW201303B (ko) * 1990-07-05 1993-03-01 Hoffmann La Roche
SE9103612D0 (sv) * 1991-12-04 1991-12-04 Astra Ab New peptide derivatives
GB9200420D0 (en) * 1992-01-09 1992-02-26 James Black Foundation The Lim Amino acid derivatives
TW223629B (ko) * 1992-03-06 1994-05-11 Hoffmann La Roche
SG48063A1 (en) * 1992-03-06 1998-04-17 Hoffmann La Roche Sulfonamidocarboxamides
DE4242655A1 (de) * 1992-12-17 1994-06-23 Behringwerke Ag Verwendung von Thrombin-Inhibitoren zur Inhibition okularer Fibrinbildung
JPH06340619A (ja) * 1993-05-03 1994-12-13 Bristol Myers Squibb Co グアニジニルまたはアミジニル置換メチルアミノ複素環トロンビン抑制剤
CA2122397A1 (en) * 1993-05-03 1994-11-04 Spencer D. Kimball Guanidinyl- or amidinyl-substituted heterocyclic thrombin inhibitors
US5783563A (en) * 1993-06-03 1998-07-21 Astra Aktiebolag Method for treatment or prophylaxis of venous thrombosis
SE9301916D0 (sv) * 1993-06-03 1993-06-03 Ab Astra New peptides derivatives
US6984627B1 (en) 1993-06-03 2006-01-10 Astrazeneca Ab Peptide derivatives
TW394760B (en) * 1993-09-07 2000-06-21 Hoffmann La Roche Novel Carboxamides, process for their preparation and pharmaceutical composition containing the same
US5770575A (en) * 1994-03-16 1998-06-23 Ortho Pharmaceutical Corporation Nipecotic acid derivatives as antithrombotic compounds
EP0684238A3 (en) * 1994-04-27 1997-01-15 Hoffmann La Roche Process for the preparation of dicarboxamides.
US5536867A (en) * 1994-04-27 1996-07-16 Hoffmann-La Roche Inc. Process for the manufacture of dicarboxamides
US5637599A (en) * 1994-06-17 1997-06-10 Corvas International, Inc. Arginine mimic derivatives as enzyme inhibitors
SE9404196D0 (sv) * 1994-12-02 1994-12-02 Astra Ab New antithrombotic formulation
US5731439A (en) * 1995-03-24 1998-03-24 The Dupont Merck Pharmaceutical Company Piperidine containing aminobornic acids
SA96170106A (ar) * 1995-07-06 2005-12-03 أسترا أكتيبولاج مشتقات حامض أميني جديدة
ATE229800T1 (de) * 1995-09-29 2003-01-15 Dimensional Pharm Inc Guanidino proteiase inhibitoren
US5792769A (en) * 1995-09-29 1998-08-11 3-Dimensional Pharmaceuticals, Inc. Guanidino protease inhibitors
DK0861236T4 (da) * 1995-11-13 2006-12-18 Sanofi Aventis Deutschland Cykliske og heterocykliske N-substituerede alphaiminohydroxam- og carboxylsyrer
TW541316B (en) * 1995-12-21 2003-07-11 Astrazeneca Ab Prodrugs of thrombin inhibitors
KR19990076817A (ko) * 1995-12-29 1999-10-15 3-디멘져널 파마슈티칼즈 인코오포레이티드 아미디노 프로테아제 억제제
ZA9756B (en) * 1996-01-16 1997-07-17 Warner Lambert Co Process for preparing 4,6-disubstituted pyrido[3,4-d]-pyrimidines
US6919375B1 (en) 1996-01-23 2005-07-19 Shionogi & Co., Ltd. Sulfonated amino acid derivatives and metalloproteinase inhibitors containing the same
ATE359264T1 (de) 1996-01-23 2007-05-15 Shionogi & Co Sulfonierte aminosäurederivate und metalloproteinase-inhibitoren, die diese enthalten
CA2242416C (en) * 1996-01-23 2006-03-21 Shionogi & Co., Ltd. Sulfonated amino acid derivatives and metalloproteinase inhibitors containing the same
US6025355A (en) 1997-05-19 2000-02-15 Cambridge Neuroscience, Inc. Pharmaceutically active compounds and methods of use
US5780480A (en) * 1996-02-28 1998-07-14 Merck & Co., Inc. Fibrinogen receptor antagonists
SE9602263D0 (sv) * 1996-06-07 1996-06-07 Astra Ab New amino acid derivatives
US5668289A (en) * 1996-06-24 1997-09-16 Merck & Co., Inc. Pyridinone thrombin inhibitors
SE9602646D0 (sv) 1996-07-04 1996-07-04 Astra Ab Pharmaceutically-useful compounds
US6242198B1 (en) 1996-07-25 2001-06-05 Cambridge Neuroscience, Inc. Methods of treatment of eye trauma and disorders
US5872138A (en) * 1996-09-13 1999-02-16 Merck & Co., Inc. Thrombin inhibitors
US5869487A (en) * 1996-10-24 1999-02-09 Merck & Co., Inc. Pyrido 3,4-B!pyrazines for use as thrombin inhibitors
SG116433A1 (en) * 1996-10-30 2005-11-28 Tanabe Seiyaku Co S type 2-substituted hydroxy-2-indolidinylbutyric ester compounds and process for preparation thereof.
US6017934A (en) * 1997-01-22 2000-01-25 Merck & Co., Inc. Thrombin inhibitors
US5792779A (en) * 1997-02-19 1998-08-11 Merck & Co., Inc. Pyridinone thrombin inhibitors
US5932606A (en) * 1997-03-24 1999-08-03 Merck & Co., Inc. Pyrazinone, pyridinone, piperidine and pyrrolidine thrombin inhibitors
DE19719621A1 (de) 1997-05-09 1998-11-12 Hoechst Ag Sulfonylaminocarbonsäuren
DK0877019T3 (da) 1997-05-09 2002-04-08 Hoechst Ag Substituerede diaminocarboxylsyrer
DE19719817A1 (de) * 1997-05-13 1998-11-19 Hoechst Ag Substituierte 6- und 7-Aminotetrahydroisochinolincarbonsäuren
AR013084A1 (es) 1997-06-19 2000-12-13 Astrazeneca Ab Derivados de amidino utiles como inhibidores de la trombina, composicion farmaceutica, utilizacion de dichos compuestos para la preparacion demedicamentos y proceso para la preparacion de los compuestos mencionados
US6011038A (en) * 1997-09-05 2000-01-04 Merck & Co., Inc. Pyrazinone thrombin inhibitors
US6087373A (en) * 1997-09-23 2000-07-11 Merck & Co., Inc. Thrombin inhibitors
US6133297A (en) * 1997-09-30 2000-10-17 Merck & Co., Inc. Thrombin inhibitors
SE9704543D0 (sv) 1997-12-05 1997-12-05 Astra Ab New compounds
US6001855A (en) * 1998-01-02 1999-12-14 Hoffman-La Roche Inc. Thiazole derivatives
SI0928793T1 (en) * 1998-01-02 2002-10-31 F. Hoffmann-La Roche Ag Thiazole derivatives
NZ508005A (en) 1998-04-24 2003-05-30 Dimensional Pharm Inc Amino acid amidinohydrazones, alkoxyguanidines and aminoguanidines useful as serine protease inhibitors
US6147078A (en) * 1998-05-19 2000-11-14 Merck & Co., Inc. Pyrazinone thrombin inhibitors
EP1082324A4 (en) * 1998-05-26 2002-01-02 Merck & Co Inc IMIDAZOPYRIDINE COMPOUNDS AS THROMBINE INHIBITORS
DE19824470A1 (de) * 1998-05-30 1999-12-02 Boehringer Ingelheim Pharma Neue Neurokininantagonisten, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende pharmazeutische Zusammensetzungen
DE59903329D1 (en) 1998-07-16 2002-12-12 Aventis Pharma Gmbh Phosphin- und phosphonsäurederivate als arzneimittel
WO2000018762A1 (en) * 1998-09-28 2000-04-06 Merck & Co., Inc. Thrombin inhibitors
EP1124823A1 (en) 1998-10-30 2001-08-22 Merck & Co., Inc. Thrombin inhibitors
US6610692B1 (en) 1998-10-30 2003-08-26 Merck & Co., Inc. Thrombin inhibitors
DE19851184A1 (de) 1998-11-06 2000-05-11 Aventis Pharma Gmbh N-Arylsulfonyl-aminosäure-omega-amide
SE9804313D0 (sv) 1998-12-14 1998-12-14 Astra Ab New compounds
EP1150996B1 (en) 1999-01-13 2007-11-21 AstraZeneca AB New amidinobenzylamine derivatives and their use as thrombin inhibitors
KR100377557B1 (ko) * 1999-02-12 2003-03-26 주식회사 엘지생명과학 아실 구아니딘 작용기를 갖는 선택적 트롬빈 억제제
JP2000302757A (ja) * 1999-04-16 2000-10-31 Shiseido Co Ltd Ｎ−置換ピペリジン誘導体
US6239132B1 (en) 1999-04-23 2001-05-29 Merck & Co., Inc. Thrombin inhibitors
EP1189618A4 (en) 1999-06-04 2002-06-19 Merck & Co Inc thrombin
UA58636C2 (uk) 1999-06-04 2003-08-15 Мерк Енд Ко., Інк. Піразинонові інгібітори тромбіну, фармацевтична композиція, спосіб інгібування утворення тромбів у крові, спосіб лікування станів, пов'язаних із тромбоутворенням
JP2003514905A (ja) 1999-11-23 2003-04-22 メルク エンド カムパニー インコーポレーテッド ピラジノン系トロンビン阻害薬
ES2189572B1 (es) * 1999-12-31 2004-06-01 Jose Manuel Valero Salinas Maquina para aplicacion de refuerzo de fibra de vidrio en encofrados desechables para columnas.
CA2403558A1 (en) 2000-03-23 2001-09-27 Merck & Co., Inc. Thrombin inhibitors
SE0001803D0 (sv) 2000-05-16 2000-05-16 Astrazeneca Ab New compounds i
US6433186B1 (en) 2000-08-16 2002-08-13 Astrazeneca Ab Amidino derivatives and their use as thormbin inhibitors
AR035216A1 (es) 2000-12-01 2004-05-05 Astrazeneca Ab Derivados de acido mandelico ,derivados farmaceuticamente aceptables, uso de estos derivados para la fabricacion de medicamentos, metodos de tratamiento ,procesos para la preparacion de estos derivados, y compuestos intermediarios
US7129233B2 (en) 2000-12-01 2006-10-31 Astrazeneca Ab Mandelic acid derivatives and their use as thrombin inhibitors
MXPA03004848A (es) * 2000-12-06 2003-08-19 Aventis Pharma Gmbh Derivados de guanidina y amidina como inhibidores del factor xa.
AR034517A1 (es) * 2001-06-21 2004-02-25 Astrazeneca Ab Formulacion farmaceutica
US7534897B2 (en) 2002-05-16 2009-05-19 Shionogi & Co., Ltd. Indole arylsulfonaimide compounds exhibiting PGD 2 receptor antagonism
SE0201661D0 (sv) * 2002-05-31 2002-05-31 Astrazeneca Ab New salts
SE0201659D0 (sv) 2002-05-31 2002-05-31 Astrazeneca Ab Modified release pharmaceutical formulation
US7781424B2 (en) * 2003-05-27 2010-08-24 Astrazeneca Ab Modified release pharmaceutical formulation
DE10344936A1 (de) * 2003-09-27 2005-04-21 Aventis Pharma Gmbh Bicyclische Iminosäurederivate als Inhibitoren von Matrix-Metalloproteinasen
WO2005062851A2 (en) * 2003-12-22 2005-07-14 Pappolla Miguel A Indole-3-propionamide and derivatives thereof
US7795205B2 (en) 2004-04-12 2010-09-14 Canyon Pharmaceuticals, Inc. Methods for effecting regression of tumor mass and size in a metastasized pancreatic tumor
TW200827336A (en) 2006-12-06 2008-07-01 Astrazeneca Ab New crystalline forms
EP2989080A1 (en) 2013-04-22 2016-03-02 Reuter Chemische Apparatebau KG Process for preparing enantiomerically enriched 3-hydroxymethylpiperidine
EP3740482A1 (en) 2018-01-17 2020-11-25 Migal Galilee Research Institute Ltd. New methionine metabolic pathway inhibitors
EP3740466B1 (en) 2018-01-17 2024-03-06 Migal Galilee Research Institute Ltd. New methionine metabolic pathway inhibitors
US20220175723A1 (en) * 2019-04-22 2022-06-09 The Penn State Research Foundation Methods and compositions relating to inhibition of aldehyde dehydrogenases for treatment of cancer

Family Cites Families (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SE420919B (sv) * 1973-08-13 1981-11-09 Mitsubishi Chem Ind Forfarande for framstellning av n?722-dansyl-l-argininderivat och farmaceutiskt godtagbara syradditionssalter derav
US4258192A (en) * 1977-12-16 1981-03-24 Mitsubishi Chemical Industries Limited N2 -Arylsulfonyl-L-argininamides and the pharmaceutically acceptable salts thereof
JPS5564561A (en) * 1978-11-10 1980-05-15 Banyu Pharmaceut Co Ltd Salicylic acid derivative, its preparation, and pharmaceutical containing the same
US4433152A (en) * 1981-05-25 1984-02-21 Nippon Chemiphar Co., Ltd. Amidinopiperidine derivatives
JPS58194861A (ja) * 1982-05-10 1983-11-12 Nippon Chemiphar Co Ltd 新規ピペリジン誘導体およびその製造法
IT1231238B (it) * 1987-09-21 1991-11-26 Angeli Inst Spa Derivati ammidinici
US5037808A (en) * 1988-07-20 1991-08-06 Monsanto Co. Indolyl platelet-aggregation inhibitors
US5053393A (en) * 1988-07-20 1991-10-01 Monsanto Company Novel platelet-aggregation inhibitor
US4879313A (en) * 1988-07-20 1989-11-07 Mosanto Company Novel platelet-aggregation inhibitors
TW201303B (ko) * 1990-07-05 1993-03-01 Hoffmann La Roche
US5254569A (en) * 1991-01-14 1993-10-19 The Du Pont Merck Pharmaceutical Company (Amidomethyl)nitrogen heterocyclic analgesics
TW223629B (ko) * 1992-03-06 1994-05-11 Hoffmann La Roche
JPH0864561A (ja) * 1994-08-23 1996-03-08 Nippon Steel Corp 化学的機械的研磨法における終点検出方法及び化学的機械的研磨装置

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102271668B1 (ko) * 2021-01-22 2021-07-02 김기련 원자력 발전소 증기발생기 랜싱 프로세스장치

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NO177704C (no) 1995-11-08
MC2261A1 (fr) 1993-04-26
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AU7949091A (en) 1992-01-09
AU650458B2 (en) 1994-06-23
IL112712A0 (en) 1995-05-26
IL98690A (en) 1996-05-14
IL112712A (en) 1996-09-12
NO177704B (no) 1995-07-31
KR100218600B1 (ko) 1999-09-01
EP0468231A2 (de) 1992-01-29
ATE111890T1 (de) 1994-10-15
PT98221A (pt) 1992-05-29
JPH04230363A (ja) 1992-08-19
ES2061125T3 (es) 1994-12-01
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CA2044636A1 (en) 1992-01-06
US5583133A (en) 1996-12-10
US5595999A (en) 1997-01-21
PT98221B (pt) 1999-01-29
IE912344A1 (en) 1992-01-15
EP0468231A3 (en) 1992-04-01
HU912206D0 (en) 1991-12-30
FI102966B1 (fi) 1999-03-31
DE59103021D1 (de) 1994-10-27
JPH0730022B2 (ja) 1995-04-05
US5393760A (en) 1995-02-28
HU217815B (hu) 2000-04-28
HUT58288A (en) 1992-02-28
US5532232A (en) 1996-07-02
FI913282A (fi) 1992-01-06
US5260307A (en) 1993-11-09
NO912626L (no) 1992-01-06
IE66047B1 (en) 1995-12-13
US5763436A (en) 1998-06-09
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IL98690A0 (en) 1992-07-15
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EP0468231B1 (de) 1994-09-21

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