KR930007904A - 방향족 아미딘 유도체 및 이의 염 - Google Patents

방향족 아미딘 유도체 및 이의 염 Download PDF

Info

Publication number
KR930007904A
KR930007904A KR1019920020309A KR920020309A KR930007904A KR 930007904 A KR930007904 A KR 930007904A KR 1019920020309 A KR1019920020309 A KR 1019920020309A KR 920020309 A KR920020309 A KR 920020309A KR 930007904 A KR930007904 A KR 930007904A
Authority
KR
South Korea
Prior art keywords
group
salt
anticoagulant
naphthyl
aromatic amidine
Prior art date
Application number
KR1019920020309A
Other languages
English (en)
Other versions
KR100205152B1 (ko
Inventor
다카야스 나가하라
나오아키 가나야
가즈에 이나무라
유키오 요코야마
Original Assignee
스즈키 다다시
다이이치세이야쿠가부시키가이샤
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 스즈키 다다시, 다이이치세이야쿠가부시키가이샤 filed Critical 스즈키 다다시
Publication of KR930007904A publication Critical patent/KR930007904A/ko
Application granted granted Critical
Publication of KR100205152B1 publication Critical patent/KR100205152B1/ko

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/44—Iso-indoles; Hydrogenated iso-indoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
    • C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
    • C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom 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
    • C07D207/12—Oxygen or sulfur atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—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
    • 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
    • C07D211/20—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—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
    • 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
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/81—Radicals substituted by nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
    • C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D333/60—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Hydrogenated Pyridines (AREA)
  • Pyrrole Compounds (AREA)
  • Furan Compounds (AREA)
  • Solid-Sorbent Or Filter-Aiding Compositions (AREA)
  • Medicinal Preparation (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Materials For Medical Uses (AREA)
  • Cultivation Of Plants (AREA)
  • Seasonings (AREA)
  • Preparation Of Compounds By Using Micro-Organisms (AREA)

Abstract

본 발명은 활성 성분으로서, 하기 일반식(Ⅰ)의 방향족 아미딘 유도체 또는 이의 염을 포함하는 항응고제에 관한 것이다.
상기식에서로 나타낸 그룹은 인돌릴, 벤조푸라닐, 벤조티에닐,
벤즈이미다졸릴, 벤즈옥사졸릴, 벤조티아졸릴, 나프틸, 테트라하이드로나프틸 및 인다닐로부터 선택된 그룹이며; X는 단일 결합, 산소 원자, 황 원자 또는 카보닐 그룹이고; Y는 치환체 그룹을 임의로 갖는 포화되거나 불포화된 5- 또는 6-원 테로사이클릭 잔기 또는 사이클릭 탄화수소 잔기, 치환체 그룹을 임의로 갖는 아미노 그룹 치환체 그룹을 임의로 가는 아미노알킬 그룹이다.
본 발명의 화합물은 이의 탁월한 FXa억제 활성에 근거하여 높은 항응고능을 갖는다.

Description

방향족 아미딘 유도체 및 이의 염
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (22)

  1. 하기 일반식(Ⅰ)의 방향족 아미딘 유도체 또는 약제학적으로 허용되는 이의 염.
  3. 상기식에서, R1은 수소원자 또는 저급 알콕시 그룹이며; R2는 수소 원자, 저급 알킬 그룹, 저급 알콕시 그룹, 카목실그룹, 알콕시카보닐 그룹, 카복시알킬 그룹 또는 알콕시 카보닐알킬 그룹이고; R3는 수소 원자, 카복실 그룹, 알콕시카보닐 그룹, 카복시알킬 그룹, 알콕시카보닐알킬 그룹, 카복시알콕시 그룹 또는 알콕시카보닐알콕시 그룹이며; R4는 수소 원자, 하이드록시 그룹, 저급 알킬 그룹 또는 저급 알콕시 그룹이고; n은 0 내지 4의 정수이며; a는 하이드록시알킬, 카복실, 알콕시카보닐, 카복시알킬 및 알콕시키보닐알킬로 이루어진 그룹으로부터 선택된 1개 또는 2개의 치환체를 가질 수 있는 가질 수 1 내지 4의 알킬렌 그룹이고; X는 단일 결합, 산소 원자, 황 원자 또는 카보닐 그룹이며, Y는 치환체 그룹을 임의로 갖는 포화되거나 불포화된 5- 또는 6-원 테로사이클릭 잔기 또는 사이클릭 탄화수소 잔기, 치환체 그룹을 임의로 갖는 아미노 그룹 치환체 그룹을 임의로 갖는 아미노알킬 그룹이고;로 나타낸 그룹은 인돌릴, 벤조푸라닐, 벤조티에닐, 벤즈이미다졸릴, 벤즈옥사졸릴, 벤조티아졸릴, 나프틸, 테트라하이드로나프틸 및 인다닐로 이루어진 그룹으로부터 선택된 원이다.
  4. 제1항에 있어서,로 나타낸 그룹이 인돌릴, 벤조푸라닐, 벤조티에닐, 벤즈이미다졸릴, 벤즈옥사졸릴, 벤조티아졸릴, 나프틸, 테트라하이드로나프틸로 이루어진 그룹으로부터 선택된 원인 방향족 아미딘 유도체 또는 이의 염.
  5. 제1항에 있어서, 포화되거나 불포화된 5- 또는 6-원 헤테로사이클릭 잔기가 질소 및 소 원자로부터 선택된 1개 또는 2개의 헤테로 원자를 함유하는 방향족 아미딘 유도체 또는 이의 염.
  6. 2-[4-[(1-아세트이미도일-3-피롤리디닐)옥시]페닐]-3-(7-아미디노-2-나프틸)프로피온산인 방향족 아미딘 유도체 또는 이의 염.
  7. (+)-2-[[(3S)-1-아세트이미도일-3-피롤리디닐)옥시]페닐]-3-(7-아미디노-2-나프틸)프로피온산인 방향족 아미딘 유도체 또는 이의 염.
  8. (2S)-2-[4-[((3S)-1-아세트이미도일-3-피롤리디닐)옥시]페닐]-3-(7-아미디노-2-나프틸)프로피온산인 방향족 아미딘 유도체 또는 이의 염.
  9. (2R)-2-[4-[((3S)-1-아세트이미도일-3-피롤리디닐)옥시]페닐]-3-(7-아미디노-2-나프틸)프로피온산인 방향족 아미딘 유도체 또는 이의 염.
  10. 2-[4-[(1-아세트이미도일-3-피롤리디닐)메톡시]페닐]-3-(5-아미디노벤조[b]티엔-2-일)프로피온산인 방향족 아미딘 유도체 또는 이의 염.
  11. (+)-2-[[((2S)-1-아세트이미도일-2-피롤리디닐)메톡시]페닐]-3-(5-아미디노벤조[b]티엔-2-일)프로피온산인 방향족 아미딘 유도체 또는 이의 염.
  12. 2-[4-[(1-아세트이미도일-4-피롤리디닐)옥시]페닐]-3-(7-아미디노-2-나프틸)프로피온산인 방향족 아미딘 유도체 또는 이의 염.
  13. (+)-2-[4-[(1-아세트이미도일-4-피롤리디닐)옥시]페닐]-3-(7-아미디노-2-나프틸)프로피온산인 방향족 아미딘 유도체 또는 이의 염.
  14. 제1항의 화합물 또는 이의 염을 활성 성분으로서 함유하는, 항응고제 또는 혈전증 또는 색전증을 예방하거나 치료하기에 유용한 제제.
  15. 제2항의 화합물 또는 이의 염을 활성 성분으로서 함유하는, 항응고제 또는 혈전증 또는 색전증을 예방하거나 치료하기에 유용한 제제.
  16. 제3항의 화합물 또는 이의 염을 활성 성분으로서 함유하는, 항응고제 또는 혈전증 또는 색전증을 예방하거나 치료하기에 유용한 제제.
  17. 제4항의 화합물 또는 이의 염을 활성 성분으로서 함유하는, 항응고제 또는 혈전증 또는 색전증을 예방하거나 치료하기에 유용한 제제.
  18. 제5항의 화합물 또는 이의 염을 활성 성분으로서 함유하는, 항응고제 또는 혈전증 또는 색전증을 예방하거나 치료하기에 유용한 제제.
  19. 제6항의 화합물 또는 이의 염을 활성 성분으로서 함유하는, 항응고제 또는 혈전증 또는 색전증을 예방하거나 치료하기에 유용한 제제.
  20. 제9항의 화합물 또는 이의 염을 활성 성분으로서 함유하는, 항응고제 또는 혈전증 또는 색전증을 예방하거나 치료하기에 유용한 제제.
  21. 제11항의 화합물 또는 이의 염을 활성 성분으로서 함유하는, 항응고제 또는 혈전증 또는 색전증을 예방하거나 치료하기에 유용한 제제.
  22. ※참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019920020309A 1991-10-31 1992-10-31 방향족 아미딘 유도체, 이의 염 및 이를 함유하는 약제 KR100205152B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP91-286088 1991-10-31
JP28608891 1991-10-31

Publications (2)

Publication Number Publication Date
KR930007904A true KR930007904A (ko) 1993-05-20
KR100205152B1 KR100205152B1 (ko) 1999-07-01

Family

ID=17699787

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019920020309A KR100205152B1 (ko) 1991-10-31 1992-10-31 방향족 아미딘 유도체, 이의 염 및 이를 함유하는 약제

Country Status (29)

Country Link
US (4) US5576343A (ko)
EP (1) EP0540051B1 (ko)
JP (2) JP2879718B2 (ko)
KR (1) KR100205152B1 (ko)
CN (3) CN1049434C (ko)
AT (1) ATE136293T1 (ko)
AU (1) AU666137B2 (ko)
BG (1) BG63237B2 (ko)
CA (1) CA2081836C (ko)
CZ (1) CZ284381B6 (ko)
DE (1) DE69209615T2 (ko)
DK (1) DK0540051T3 (ko)
EE (1) EE03024B1 (ko)
ES (1) ES2088073T3 (ko)
FI (1) FI107923B (ko)
GR (1) GR3019832T3 (ko)
HK (1) HK1002999A1 (ko)
HR (1) HRP921147B1 (ko)
HU (1) HU221976B1 (ko)
IL (1) IL103564A (ko)
MX (1) MX9206295A (ko)
NO (1) NO302948B1 (ko)
NZ (1) NZ244936A (ko)
PL (1) PL170312B1 (ko)
RU (1) RU2139851C1 (ko)
SG (1) SG78251A1 (ko)
SK (1) SK327692A3 (ko)
TW (1) TW210998B (ko)
ZA (1) ZA928276B (ko)

Families Citing this family (126)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6087380A (en) 1949-11-24 2000-07-11 Boehringer Ingelheim Pharma Kg Disubstituted bicyclic heterocycles, the preparations and the use thereof as pharmaceutical compositions
IL110172A (en) * 1993-07-22 2001-10-31 Lilly Co Eli Bicycle compounds and pharmaceuticals containing them
US5731324A (en) * 1993-07-22 1998-03-24 Eli Lilly And Company Glycoprotein IIb/IIIa antagonists
US6448269B1 (en) 1993-07-22 2002-09-10 Eli Lilly And Company Glycoprotein IIb/IIIa antagonists
US6137002A (en) * 1993-07-22 2000-10-24 Eli Lilly And Company Glycoprotein IIb/IIIa antagonists
CA2134192A1 (en) * 1993-11-12 1995-05-13 Michael L. Denney 5, 6-bicyclic glycoprotein iib/iiia antagonists
CA2168858A1 (en) * 1994-06-06 1995-12-14 Shinichiro Ono Novel fused-ring carboxylic acid compound or salt thereof, and medicinal use thereof
US5869501A (en) * 1994-12-02 1999-02-09 Yamanouchi Pharmaceutical Co. Ltd Amidinonaphthyl derivative or salt thereof
US5691364A (en) * 1995-03-10 1997-11-25 Berlex Laboratories, Inc. Benzamidine derivatives and their use as anti-coagulants
PT813525E (pt) * 1995-03-10 2004-02-27 Berlex Lab Derivados de benzamidina e sua utilizacao como anticoagulantes
US5612363A (en) * 1995-06-02 1997-03-18 Berlex Laboratories, Inc. N,N-di(aryl) cyclic urea derivatives as anti-coagulants
DE19530996A1 (de) * 1995-08-23 1997-02-27 Boehringer Mannheim Gmbh Cyclische Guanidine, Verfahren zu ihrer Herstellung und Arzneimittel
US5849759A (en) * 1995-12-08 1998-12-15 Berlex Laboratories, Inc. Naphthyl-substituted benzimidazole derivatives as anti-coagulants
US5939418A (en) * 1995-12-21 1999-08-17 The Dupont Merck Pharmaceutical Company Isoxazoline, isothiazoline and pyrazoline factor Xa inhibitors
US5994375A (en) * 1996-02-12 1999-11-30 Berlex Laboratories, Inc. Benzamidine derivatives substituted by amino acid and hydroxy acid derivatives and their use as anti-coagulants
DE19612828C1 (de) * 1996-03-30 1997-02-27 Boehringer Mannheim Gmbh Verfahren zur Herstellung von Naphthonitrilderivaten und deren Verwendung zur Herstellung von Faktor-Xa-Inhibitoren
EP0918768B1 (en) * 1996-05-31 2002-01-09 C & C Research Laboratories Aromatic amidine derivatives useful as selective thrombin inhibitors
AU3645697A (en) * 1996-07-08 1998-02-02 Du Pont Pharmaceuticals Company Amidinoindoles, amidinoazoles, and analogs thereof as inhibitors of factor xa and of thrombin
US5977138A (en) * 1996-08-15 1999-11-02 Schering Corporation Ether muscarinic antagonists
US5693641A (en) * 1996-08-16 1997-12-02 Berlex Laboratories Inc. Bicyclic pyrimidine derivatives and their use as anti-coagulants
US5753635A (en) * 1996-08-16 1998-05-19 Berlex Laboratories, Inc. Purine derivatives and their use as anti-coagulants
TW430652B (en) * 1996-09-06 2001-04-21 Daiichi Seiyaku Co Process for preparing 2-phenyl-3-naphthyl propionic acid derivatives
CA2264521A1 (en) 1996-09-12 1998-03-19 Schering Aktiengesellschaft Benzamidine derivatives substituted by cyclic amino acid or cyclic hydroxy acid derivatives and their use as anti-coagulants
US6008234A (en) * 1996-09-12 1999-12-28 Berlex Laboratories, Inc. Benzamidine derivatives substituted by cyclic amino acid and cyclic hydroxy acid derivatives and their use as anti-coagulants
US6004985A (en) * 1996-10-09 1999-12-21 Berlex Laboratories, Inc. Thio acid derived monocylic N-heterocyclics as anticoagulants
EP0842941A1 (de) * 1996-11-16 1998-05-20 Roche Diagnostics GmbH Neue Phosphonate, Verfahren zu ihrer Herstellung und Arzneimittel
WO1998026803A1 (fr) * 1996-12-19 1998-06-25 Daiichi Pharmaceutical Co., Ltd. Composition pharmaceutique pour administration par voie orale
SE9604744D0 (sv) * 1996-12-20 1996-12-20 Pharmacia & Upjohn Ab A modified coagulation agent
PE121699A1 (es) * 1997-02-18 1999-12-08 Boehringer Ingelheim Pharma Heterociclos biciclicos disustituidos como inhibidores de la trombina
US7109326B2 (en) 1997-04-15 2006-09-19 Genentech, Inc. Halo-alkoxycarbonyl prodrugs
US6271227B1 (en) 1997-04-30 2001-08-07 Eli Lilly And Company Antithrombotic Agents
CA2288224A1 (en) 1997-04-30 1998-11-05 Mary George Johnson Antithrombotic agents
US6350774B1 (en) 1997-04-30 2002-02-26 Eli Lilly And Company Antithrombotic agents
JP2001523255A (ja) * 1997-04-30 2001-11-20 イーライ・リリー・アンド・カンパニー 抗血栓剤
AU7170798A (en) * 1997-04-30 1998-11-24 Eli Lilly And Company Antithrombotic agents
JP2002514217A (ja) 1997-04-30 2002-05-14 イーライ・リリー・アンド・カンパニー 抗血栓物質
DE69819539T2 (de) 1997-05-01 2004-09-30 Eli Lilly And Co., Indianapolis Antithrombotische mittel
TW513402B (en) * 1997-05-30 2002-12-11 Daiichi Seiyaku Co Process for preparing 3-(7-amidino-2-naphthyl)-2-phenylpropionic acid derivatives
FR2764511B1 (fr) * 1997-06-13 2000-09-08 Sanofi Sa Compositions pour le traitement et la prevention de la thrombose arterielle et utilisation d'un inhibiteur du facteur xa seul et/ou en combinaison avec un antiagregant plaquettaire
WO1999000128A1 (en) 1997-06-26 1999-01-07 Eli Lilly And Company Antithrombotic agents
AU735144B2 (en) 1997-07-23 2001-07-05 Yamanouchi Pharmaceutical Co., Ltd. Novel hexahydro-1,4-diazepine derivatives or their salts
ZA986594B (en) * 1997-07-25 1999-01-27 Abbott Lab Urokinase inhibitors
US6258822B1 (en) 1997-08-06 2001-07-10 Abbott Laboratories Urokinase inhibitors
US5886191A (en) * 1997-08-18 1999-03-23 Dupont Pharmaceuticals Company Amidinoindoles, amidinoazoles, and analogs thereof
US6740682B2 (en) 1997-08-29 2004-05-25 Tularik Limited Meta-benzamidine derivatives as serine protease inhibitors
WO1999011617A1 (fr) * 1997-09-01 1999-03-11 Yamanouchi Pharmaceutical Co., Ltd. Nouveaux derives de naphtamide et sels de ces derives
US6207697B1 (en) 1997-09-09 2001-03-27 Dupont Pharmaceuticals Company Benzimidazolinones, benzoxazolinones, benzopiperazinones, indanones, and derivatives thereof as inhibitors of factor Xa
DE19743435A1 (de) * 1997-10-01 1999-04-08 Merck Patent Gmbh Benzamidinderivate
EP1030844A1 (en) * 1997-11-10 2000-08-30 Array Biopharma Inc. Compounds which inhibit tryptase activity
US6150379A (en) * 1997-11-26 2000-11-21 Axys Pharmaceuticals, Inc. Compounds and compositions as anticoagulants
WO1999026932A1 (en) * 1997-11-26 1999-06-03 Axys Pharmaceuticals, Inc. By amidino group substituted heterocyclic derivatives and their use as anticoagulants
WO1999026933A1 (en) * 1997-11-26 1999-06-03 Axys Pharmaceuticals, Inc. Substituted amidinoaryl derivatives and their use as anticoagulants
KR19990043605A (ko) * 1997-11-29 1999-06-15 이경하 선택적 트롬빈 억제제로 유용한 방향족 아미딘유도체
US6686364B2 (en) 1997-12-08 2004-02-03 Berlex Laboratories, Inc. Benzamidine derivatives and their use as anti-coagulants
US6140351A (en) * 1997-12-19 2000-10-31 Berlex Laboratories, Inc. Ortho-anthranilamide derivatives as anti-coagulants
NZ503809A (en) * 1997-12-19 2002-04-26 Schering Ag Ortho-anthranilamide derivatives as anti-coagulants
US6114532A (en) * 1998-02-03 2000-09-05 Boehringer Ingelheim Pharma Kg Bicyclic heterocycles, the preparation thereof, and their use as pharmaceuticals
AU2720199A (en) * 1998-02-03 1999-08-23 Boehringer Ingelheim Pharma Kg Five-membered, benzo-condensed heterocycles used as antithrombotic agents
EP0937723A1 (de) * 1998-02-18 1999-08-25 Roche Diagnostics GmbH Neue Sulfonamide, Verfahren zu ihrer Herstellung sowie diese enthaltende Arzneimittel
KR19990074598A (ko) * 1998-03-12 1999-10-05 성재갑 고체상 반응을 이용한 벤즈아미딘 유도체의 신규한 제조방법
AP1224A (en) 1998-03-19 2003-11-14 Bristol Myers Squibb Co Biphasic controlled release delivery system for high solubility pharmaceuticals and method.
HUP0101137A3 (en) 1998-04-10 2003-03-28 Japan Tobacco Inc Anticoagulant amidines and their pharmaceutical use
US6284756B1 (en) 1998-04-30 2001-09-04 Eli Lilly And Company Antithrombotic agents
DE19834751A1 (de) * 1998-08-01 2000-02-03 Boehringer Ingelheim Pharma Disubstituierte bicyclische Heterocyclen, ihre Herstellung und ihre Verwendung als Arzneimittel
US6284796B1 (en) 1998-08-06 2001-09-04 Abbott Laboratories Ukokinase inhibitors
US6504031B1 (en) 1998-08-06 2003-01-07 Milan Bruncko Naphthamidine urokinase inhibitors
DE19839499A1 (de) * 1998-08-29 2000-03-02 Merck Patent Gmbh 2-Oxo-2H-chinolinderivate
JP2000080046A (ja) 1998-09-03 2000-03-21 Dai Ichi Seiyaku Co Ltd 多臓器障害の予防・治療剤
US6362216B1 (en) 1998-10-27 2002-03-26 Array Biopharma Inc. Compounds which inhibit tryptase activity
CA2287549A1 (en) * 1998-10-28 2000-04-28 Jefferson Ray Mccowan Antithrombotic agents
US6262088B1 (en) 1998-11-19 2001-07-17 Berlex Laboratories, Inc. Polyhydroxylated monocyclic N-heterocyclic derivatives as anti-coagulants
US6127376A (en) 1998-12-04 2000-10-03 Berlex Laboratories, Inc. Aryl and heterocyclyl substituted pyrimidine derivatives as anti-coagulants
DE69919743T2 (de) 1998-12-14 2005-09-01 F. Hoffmann-La Roche Ag Phenylglycin-derivate
US6689780B1 (en) 1998-12-23 2004-02-10 Eli Lilly And Company Heteroroaromatic amides as inhibitor of factor Xa
AU2381600A (en) 1998-12-23 2000-07-31 Du Pont Pharmaceuticals Company Thrombin or factor xa inhibitors
WO2000039117A1 (en) * 1998-12-23 2000-07-06 Eli Lilly And Company HETEROROAROMATIC AMIDES AS INHIBITOR OF FACTOR Xa
CN100488947C (zh) 1999-01-13 2009-05-20 杰南技术公司 丝氨酸蛋白酶抑制剂
FR2793687B1 (fr) * 1999-04-26 2001-08-24 Sanofi Sa Nouvelle composition injectable d'un anticoagulant
FR2793247B1 (fr) * 1999-05-04 2001-06-22 Synthelabo Derives de 6-[[(aryl et heteroaryl)oxy]methyl]naphtalene-2- carboximidamide, leur preparation et leur application en therapeutique
AU5102800A (en) * 1999-05-31 2000-12-18 Daiichi Pharmaceutical Co., Ltd. Remedies for periodontal diseases
WO2001002356A1 (fr) * 1999-07-01 2001-01-11 Sankyo Company, Limited Dérivés d'indoline ou tétrahydroquinoline
US6350761B1 (en) * 1999-07-30 2002-02-26 Berlex Laboratories, Inc. Benzenamine derivatives as anti-coagulants
GB9924155D0 (en) * 1999-10-12 1999-12-15 Rhone Poulenc Rorer Pharma Chemical compounds
ES2250196T3 (es) * 1999-08-26 2006-04-16 Aventis Pharmaceuticals Inc. Aminoiminometil o aminometil dihidrobenzofuranos y benzopiranos sustituidos.
US6844367B1 (en) 1999-09-17 2005-01-18 Millennium Pharmaceuticals, Inc. Benzamides and related inhibitors of factor Xa
KR100642953B1 (ko) 1999-10-28 2006-11-10 상꾜 가부시키가이샤 벤즈아미딘 유도체
AU2108601A (en) * 1999-12-15 2001-06-25 Axys Pharmaceuticals, Inc. Salicylamides as serine protease inhibitors
US20030065176A1 (en) * 2000-01-29 2003-04-03 Myung-Gyun Kang Factor xa inhibitors with aryl-amidines and derivatives, and prodrugs thereof
WO2001056989A2 (en) * 2000-02-01 2001-08-09 Cor Therapeutics, Inc. Inhibitors of factor xa
US20020072530A1 (en) * 2000-02-01 2002-06-13 Bing-Yan Zhu Indole and benzimidazole inhibitors of factor Xa
DK1259485T3 (da) 2000-02-29 2006-04-10 Millennium Pharm Inc Benzamider og beslægtede inhibitorer for faktor Xa
US20030225036A1 (en) * 2000-03-20 2003-12-04 Aleksandr Kolesnikov Non-amidine containing protease inhibitors
JP2001261674A (ja) * 2000-03-22 2001-09-26 Mitsui Chemicals Inc ベンゾチオフェン誘導体およびそれを有効成分として含有する核内レセプター作動薬
DE10014645A1 (de) 2000-03-24 2001-09-27 Merck Patent Gmbh Substituierte Biphenylderivate
ES2260222T3 (es) * 2000-04-25 2006-11-01 Abbott Laboratories Naftamidina que inhibe la uroquinasa.
US6495562B1 (en) 2000-04-25 2002-12-17 Abbott Laboratories Naphthamidine urokinase inhibitors
US20020037912A1 (en) * 2000-08-11 2002-03-28 Leahy Ellen M. Factor viia inhibitors
AU2002246336B2 (en) 2001-04-05 2005-05-19 Sankyo Company, Limited Benzamidine derivative
TWI240723B (en) * 2001-06-20 2005-10-01 Wyeth Corp Substituted naphthyl benzofuran derivatives as inhibitors of plasminogen activator inhibitor-1 (PAI-1)
DE10130718A1 (de) * 2001-06-26 2003-01-02 Merck Patent Gmbh Kohlenhydratderivate
CA2452391A1 (en) * 2001-07-09 2003-01-23 Axys Pharmaceuticals, Inc. 2-[5-(5-carbamimidoyl-1h-heteroaryl)-6-hydroxybiphenyl-3-yl]-succinic acid derivatives as factor viia inhibitors
DE10139060A1 (de) 2001-08-08 2003-02-20 Merck Patent Gmbh Phenylderivate
WO2003040086A1 (fr) * 2001-11-09 2003-05-15 Kissei Pharmaceutical Co., Ltd. Derives de 5-amidino-2-hydroxybenzene-sulfonamide, composition medicinales les contenant, leur utilisation medicale et produits intermediaires utilises dans le cadre de leur production
US20030181488A1 (en) 2002-03-07 2003-09-25 Boehringer Ingelheim Pharma Gmbh & Co. Kg Administration form for the oral application of 3-[(2-{[4-(hexyloxycarbonylamino-imino-methyl)-phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionic acid ethyl ester and the salts thereof
UA80131C2 (en) * 2002-05-28 2007-08-27 Dimensional Pharm Inc Thiophene amidines, compositions thereof, and methods of treating complement-mediated diseases and conditions
JP2006096668A (ja) * 2002-11-08 2006-04-13 Ono Pharmaceut Co Ltd エラスターゼ阻害剤と血液凝固系および／または線溶系酵素阻害剤との組み合わせからなる医薬
CN100513398C (zh) 2002-12-03 2009-07-15 Axys药物公司 作为因子viia抑制剂的2-(2-羟基联苯-3-基)-1h-苯并咪唑-5-甲脒衍生物
DE10302500A1 (de) 2003-01-23 2004-07-29 Merck Patent Gmbh Carbonsäureamidderivate
DE10308907A1 (de) 2003-02-28 2004-09-09 Merck Patent Gmbh Ethynylderivate
DE10339862A1 (de) 2003-08-29 2005-03-24 Boehringer Ingelheim Pharma Gmbh & Co. Kg 3-[(2-{[4-(Hexyloxycarbonylamino-imino-methyl)- phenylamino]-methyl}-1-methyl-1H-benzimidazol-5-carbonyl)-pyridin-2-yl-amino]-propionsäure-ethylester-Methansulfonat und dessen Verwendung als Arzneimittel
CA2540826A1 (en) * 2003-10-01 2005-04-14 The Procter & Gamble Company Melanin concentrating hormone antagonists
CN1605336A (zh) 2003-10-10 2005-04-13 中国医学科学院药物研究所 左旋丁基苯酞在制备预防和治疗脑梗塞的药物中的应用
TWI396686B (zh) 2004-05-21 2013-05-21 Takeda Pharmaceutical 環狀醯胺衍生物、以及其製品和用法
JP2006036710A (ja) * 2004-07-28 2006-02-09 Mitsui Chemicals Inc 光学活性な３−ヒドロキシテトラヒドロフランの製造法
GB2431927B (en) 2005-11-04 2010-03-17 Amira Pharmaceuticals Inc 5-Lipoxygenase-activating protein (FLAP) inhibitors
US8399666B2 (en) 2005-11-04 2013-03-19 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
US7977359B2 (en) 2005-11-04 2011-07-12 Amira Pharmaceuticals, Inc. 5-lipdxygenase-activating protein (FLAP) inhibitors
EP1800727A1 (en) * 2005-12-20 2007-06-27 DSMIP Assets B.V. Process for the treatment of an aqueous mixture comprising a dipolar aprotic compound
ES2382055T3 (es) 2006-11-02 2012-06-04 Millennium Pharmaceuticals, Inc. Métodos para sintetizar sales farmacéuticas de un inhibidor del factor Xa
US8227492B2 (en) * 2007-08-07 2012-07-24 Cadila Healthcare Limited Sulfoxamine derivatives as factor Xa inhibitors
TW200920369A (en) 2007-10-26 2009-05-16 Amira Pharmaceuticals Inc 5-lipoxygenase activating protein (flap) inhibitor
MX2010012814A (es) 2008-05-23 2010-12-20 Amira Pharmaceuticals Inc Inhibidor de proteina activadora de 5-lipoxigenasa.
JP2011522882A (ja) * 2008-06-12 2011-08-04 コリア インスティテュート オブ サイエンス アンド テクノロジー β−アミロイドフィブリル形成阻害剤として作用するスチリルベンゾフラン誘導体及びその製造方法
US8546431B2 (en) 2008-10-01 2013-10-01 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
CA2804926C (en) 2010-07-09 2019-01-08 James Trinca Green Combination immediate/delayed release delivery system for short half-life pharmaceuticals including remogliflozin
PT3307734T (pt) 2015-06-09 2020-02-25 Abbvie Inc Moduladores de recetores nucleares (ror) para o tratamento de doenças inflamatórias e autoimunes

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1050302A (ko) * 1964-02-19
AU527371B2 (en) * 1980-09-16 1983-03-03 Torii & Co., Ltd. Amidine
US4681886A (en) * 1982-04-30 1987-07-21 E. R. Squibb & Sons, Inc. Substituted 4-phenoxy or 4-phenylthio prolines
JPS59139357A (ja) * 1983-01-28 1984-08-10 Torii Yakuhin Kk アミジン誘導体
US4563527A (en) * 1984-07-19 1986-01-07 Torii & Co., Ltd. Amidine compounds
EP0313943B1 (en) * 1987-10-20 1993-08-04 MITSUI TOATSU CHEMICALS, Inc. 1,2-naphtalocyanine near-infrared absorbent and recording/display materials using same
US5256812A (en) * 1989-01-31 1993-10-26 Hoffmann-La Roche Inc. Carboxamides and sulfonamides
US4952562A (en) * 1989-09-29 1990-08-28 Rorer Pharmaceutical Corporation Anti-thrombotic peptides and pseudopeptides
US5258398A (en) * 1991-12-16 1993-11-02 Rhone-Poulenc Rorer Pharmaceuticals Inc. Antithrombotic diaminoalkanoic acid derivatives
JPH08176139A (ja) * 1994-12-20 1996-07-09 Tokuyama Corp クロメン化合物

Also Published As

Publication number Publication date
NZ244936A (en) 1995-05-26
US5576343A (en) 1996-11-19
BG63237B2 (bg) 2001-06-29
CA2081836C (en) 2005-04-12
NO924164D0 (no) 1992-10-29
HK1002999A1 (en) 1998-09-30
ATE136293T1 (de) 1996-04-15
KR100205152B1 (ko) 1999-07-01
JP3461441B2 (ja) 2003-10-27
CN1168886A (zh) 1997-12-31
US5620991A (en) 1997-04-15
IL103564A (en) 1998-12-06
HRP921147B1 (en) 1999-04-30
FI107923B (fi) 2001-10-31
PL170312B1 (pl) 1996-11-29
PL296439A1 (en) 1993-08-23
FI924932A0 (fi) 1992-10-30
FI924932A (fi) 1993-05-01
US5866577A (en) 1999-02-02
ZA928276B (en) 1993-05-06
NO924164L (no) 1993-05-03
DE69209615T2 (de) 1997-01-09
CN1072677A (zh) 1993-06-02
IL103564A0 (en) 1993-03-15
EE03024B1 (et) 1997-08-15
SK279807B6 (sk) 1999-04-13
CZ327692A3 (en) 1993-05-12
US5962695A (en) 1999-10-05
DE69209615D1 (de) 1996-05-09
SK327692A3 (en) 1999-04-13
JP2879718B2 (ja) 1999-04-05
RU2139851C1 (ru) 1999-10-20
CN1097052C (zh) 2002-12-25
CN1062865C (zh) 2001-03-07
TW210998B (ko) 1993-08-11
GR3019832T3 (en) 1996-08-31
EP0540051A1 (en) 1993-05-05
CN1049434C (zh) 2000-02-16
CA2081836A1 (en) 1993-05-01
HUT65890A (en) 1994-07-28
DK0540051T3 (da) 1996-05-06
ES2088073T3 (es) 1996-08-01
HU9203433D0 (en) 1993-01-28
JPH10291931A (ja) 1998-11-04
HRP921147A2 (ko) 1995-10-31
SG78251A1 (en) 2001-02-20
NO302948B1 (no) 1998-05-11
AU666137B2 (en) 1996-02-01
CZ284381B6 (cs) 1998-11-11
EP0540051B1 (en) 1996-04-03
JPH05208946A (ja) 1993-08-20
AU2747092A (en) 1993-05-06
HU221976B1 (hu) 2003-03-28
CN1168885A (zh) 1997-12-31
MX9206295A (es) 1993-08-01

Similar Documents

Publication Publication Date Title
KR930007904A (ko) 방향족 아미딘 유도체 및 이의 염
ES2092580T3 (es) Derivado de 2-ariltiazol y composicion farmaceutica que contiene el mismo.
KR920000754A (ko) 환식아미드 유도체
EA200100755A1 (ru) 4-оксо-1,4-дигидро-3-хинолинкарбоксамиды как антивирусные агенты
KR910009672A (ko) 피리다진 유도체, 이의 제조방법 및 이것을 함유하는 약학 조성물
KR900016098A (ko) 카페인산의 유도체 및 이를 함유하는 약제학적 조성물
NO20020804L (no) Nye A-500359-derivater
KR927003564A (ko) 크로몬 유도체 및 이 화합물을 유효성분으로 하는 아르도스 리덕타제 저해제
KR900009640A (ko) 벤족 사제핀 유도체
KR950704252A (ko) N-치환 이미다졸 유도체
KR970032864A (ko) 골다공증 치료제
ES454285A1 (es) Procedimiento para preparar derivados de 4-amina trans-deca-hidroquinolina.
KR910020176A (ko) 알도스 환원효소 저해제
KR890002180A (ko) 세팔로스포린 유도체

Legal Events

Date Code Title Description
A201 Request for examination
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
FPAY Annual fee payment

Payment date: 20060327

Year of fee payment: 8

LAPS Lapse due to unpaid annual fee