KR910000658A - 이미다졸릴- 알케노산 - Google Patents

이미다졸릴- 알케노산 Download PDF

Info

Publication number
KR910000658A
KR910000658A KR1019900008739A KR900008739A KR910000658A KR 910000658 A KR910000658 A KR 910000658A KR 1019900008739 A KR1019900008739 A KR 1019900008739A KR 900008739 A KR900008739 A KR 900008739A KR 910000658 A KR910000658 A KR 910000658A
Authority
KR
South Korea
Prior art keywords
methyl
compound
alkyl
formula
thienyl
Prior art date
Application number
KR1019900008739A
Other languages
English (en)
Other versions
KR0165837B1 (ko
Inventor
알란 핀켈스타인 조셉
와인스톡 조셉
맥쿨로치 키이난 리챠드
Original Assignee
스튜아트 알. 슈터
스미스클라인 비참 코포레이션
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 스튜아트 알. 슈터, 스미스클라인 비참 코포레이션 filed Critical 스튜아트 알. 슈터
Publication of KR910000658A publication Critical patent/KR910000658A/ko
Application granted granted Critical
Publication of KR0165837B1 publication Critical patent/KR0165837B1/ko

Links

Classifications

    • 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
    • C07D233/58—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 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring nitrogen 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
    • C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/415—1,2-Diazoles
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A61P27/06—Antiglaucoma agents or miotics
    • 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
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/02—Non-specific cardiovascular stimulants, e.g. drugs for syncope, antihypotensives
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/08—Vasodilators for multiple indications
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • 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
    • C07D233/66—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 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
    • C07D233/70—One oxygen atom
    • 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
    • C07D401/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D403/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D405/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D409/06—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 carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • Public Health (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Cardiology (AREA)
  • Ophthalmology & Optometry (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Endocrinology (AREA)
  • Reproductive Health (AREA)
  • Epidemiology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Medicinal Preparation (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
  • Polishing Bodies And Polishing Tools (AREA)
  • External Artificial Organs (AREA)

Abstract

내용 없음

Description

이미다졸릴-알케노산
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (17)

  1. 일반식(Ⅰ)의 화합물 또는 약제학적으로 허용되는 염.
  3. R1은 비치환되거나, Cl, Br, F, I C1-C4알킬, 니트로, CO2R7, 테트라졸-5-일, C1-C4알콕시, 하이드록시, SC1-C4알킬, SO2NHR7, SO3H, CONR7R7, CN, SO2C1-C4알킬 및 CnF2n+1(여기에서 n은 1내지 3이다)중에서 선택된 하나 내지 3개의 치환체에 의해 치환된, 페닐, 비페닐, 나프틸, 또는 아다만틸 메틸이고: R2는 비치환되거나, C1-C4알킬, 니트로, Cl, Br, F, I, 하이드록실, C1-C4알콕시, NR7R7, CO2R7, CN 및 CONR7R7중에서 선택된 1 내지 3개의 치환체에 의해 치환된, C2-C10알킬, C3-C10알케닐, C3-C10알키닐, C3-C6사이클로알킬 또는 (CH2)0-8페닐이며: X는 단일결합, S 또는 O이고: R3은 수소, Cl, Br, F, I, CHO, 하이드록시메틸, COOR7, CONR7R7, NO2, 또 CnF2n+1(여기에서 n은 1내지 3이다)이며: R4및 R5는 독립적으로 수소, C1-C6알킬, 티에닐-Y-, 피라졸릴-Y-, 이미다졸릴-Y-, 티아졸리-Y-, 푸릴-Y-, 피롤릴-Y, 티아졸릴-Y-, 옥사졸릴-Y-, 이속사졸릴-Y-, 피리딜-Y- 또는 테트라졸릴-Y-이고, 단 R4및 R5는 모두 수소 및 C1-C4알킬 중에서 선택되어서는 안되며, 헤테로 사이클릭 환은 각각 비치환되거나, C1-C4알킬, C1-C4알콕시, Cl, Br, F, I, NR7R7, CO2R7, SO2NHR7, SO3H 또는 CONR7R|7에 의해 치환되어야 하고: Y는 단일결합, S, O 또는 직쇄 또는 측쇄이거나 페닐 또는 벤질로 임의 치환된 C1-C6알킬이며, 여기에서 아릴그룹은 각각 비치환되거나 할로, NO2, CF3, C1-C4알킬, C1-C4알콕시, CN, 또는 CO2R7에 의해 치환되고, R6는 -Z-COOR8또는 -Z-CONR7R7이며: Z는 단일결합: 비닐: -CH2-O-CH2-: C1-C4알킬, 페닐, 벤질, 티에닐메틸 또는 푸릴메틸이다)이고: R7는 각각 독립적으로 수소, C1-C4알킬, 또는 (CH2)m페닐(여기에서 m은 0내지 4이다)이며: R8은 수소, C1-C6알킬, 또는 2-디(C|1-C4알킬)아미노-2-옥소에틸이다.
  4. 제1항에 있어서, R1이 비치환되거나, 클로로, 플루오로, 트리플루오로메틸, 니트로, 메틸, 메톡시, 하이드록시, 설파이드, 시아노, 카복시, 카보-C1-C4알콕시, 카바모일 및 테트라졸-5-일 중에서 선택된 하나 내지 3개의 치환체에 의해 치환된 페닐이고: X가 단일결합이며; R2가 C2-C8알킬이고: R3가 수소, 클로로, 플루오로 또는 트리플루오로 메틸이며: R4가 수소, 또는 C1-C4알킬이고: R5가 각각 메틸 또는 메톡시에의해 임의로 치환된 티에틸메틸, 푸릴메틸, 이미다졸릴메틸 또는 피리딜메틸이며: R6가 COOH, COOC1-C2알킬, CONH2인 화합물.
  5. 제1항 또는 제2항에 있어서, E(트랜스)이성체인 화합물.
  6. 제1항에 있어서, (E)-3-[2-n-부틸-1-{(4-카복시페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산 또는 이의 약제학적으로 허용되는 염.
  7. 제1항에 있어서, (E)-3-[2-n-부틸-1-{(4-카복시-3-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산 또는 이의 약제학적으로 허용되는 염.
  8. 제1항에 있어서, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(4-카복시-2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(4-카복메톡시 페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-헥실-1-{(4-카복시 페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-프로필-1-{(4-카복시페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-니트로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-푸릴)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(4-이미다졸릴)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(3-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(5-메틸-2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-시아노페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(4-메톡시-3-메틸페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(4-피리딜)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2-클로로페닐)메틸}-1H-이미다졸-5-일]-2-(5-메톡시-2-티에닐)메틸-2-프로페논산, (E)-3-[2-n-부틸-1-{(2,3-디클로로페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산, 또는 (E)-3-[2-n-부틸-1-{(2-트리플루오로메틸페닐)메틸}-1H-이미다졸-5-일]-2-(2-티에닐)메틸-2-프로페논산: 또는 이의 약제학적으로 허용되는 염.
  9. 제1항 내지 제6항중 어느 한항에 따르는 화합물 및 이의 약제학적으로 허용되는 담체를 함유하는 약제학적 조성물.
  10. a)일반식(Ⅱ)의 화합물을 염기의 존재하에서 (C1-C4알콕시)2P(O)CH(R5)COOC1-C6알킬(여기에서 R5는 제1항에서 정의한 바와 같다)과 반응시키거나, b)일반식(Ⅲ)의 화합물을 일반식(Ⅳ)의 화합물과 반응시키거나, c)일반식(Ⅱ)의 화합물을 염기의 존재하에서 일반식(Ⅴ)의 화합물과 반응시키거나, d)일반식(Ⅳ)의 화합물을 염기와 반응시키거나, c)일반식(Ⅱ)의 화합물을 아세트산 무수물 중에서 염기의 존재하에 적절한 헤테로 사이클릭 아세트산과 반응시킨후: (i)상기와 같이 제조된 일반식(Ⅰ)의 에스테르 화합물을 환원시키고, 이어서, C1-C6알킬 할로아세테이트와 반응시켜 Z가 -CH2-O-CH2- 인 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅱ)상기와 같이 제조된 일반식(Ⅰ)의 에스테르 화합물을 가수분해시키고, 이어서 아미노생성시약의 존재하에서 적절히 치환된 아미노산과 반응시켜 Z가 -C(O)NHCHR9-이고 R9이 수소, C1-C4알킬, 페닐, 벤질, 티에닐 메틸, 또는 푸릴메틸인 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅲ)상기와 같이 제조된 일반식(Ⅰ)의 에스테르 화합물을 환원시키고, 이어서 C1-C6알킬과 반응시킨후 포스핀 리간드의 존재하에서 일산화탄소와 반응시켜 Z가 메틸렌그룹인 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅳ)Z가 케틸렌그룹인 상기와 같이 제조된 일반식(Ⅰ)의 에스테르 화합물을 리튬 디알킬아미드와 반응시키고, 이어서 알킬화제와 반응시켜 Z가 C1-C4알킬, 벤질, 티에닐 메틸 또는 푸릴메틸에 의해 치환된 메틸렌그룹인 일반식(Ⅰ)의 화합물을 생성시킨후: 필요한 경우 (i)R1그룹이 C1-C4알콕시에 의해 치환된 일반식(Ⅰ)의 화합물을 탈보호시켜 R1그룹이 하이드록시에 의해 치환된 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅱ)R1그룹이 CO2C1-C|4알킬에 의해 치환된 일반식(Ⅰ)의 화합물을 가수분해시켜 R1그룹이 카복시에 의해 치환된 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅲ)R1그룹이 카복시에 의해 치환된 일반식(Ⅰ)의 화합물을 할로겐화제로 처리하고, 이어서 암모니아와 반응시켜 1급 아미드로 전환시키고, 옥살릴클로라이드/디케틸포름아미드로 탈수시키고, 아지드와 반응시켜, R1그룹이 테트라졸-5-일 그룹에 의해 치환된 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅳ)R6가 -Z-COOC1-C6알킬인 일반식(Ⅰ)의 화합물을 가수분해시켜 R6가 -Z-COOH인 일반식(Ⅰ)의 화합물을 생성시키거나, (ⅴ)R6가 -Z-COOH인 일반식(Ⅰ)의 화합물을 할로겐화제로 처리하고, 이어서 적절히 치환된 아민과 반응시켜 R6가 -Z-CONR7R7이고 R7가 수소, C1-C4알킬 또는 (CH2)0-4페닐인 일반식(Ⅰ)의 화합물을 생성시킨후: 임의로 약제학적으로 허용되는 염을 형성시킴을 특징으로 하여, 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염을 제조하는 방법.
  12. 상기식에서, R2,R3,R4,R5및 X는 제1항에서 정의한 바와 같고:R|1′는 제1항에서 정의한 R1이며, 단 R1′그룹상의 치환체는 테트라졸-5-일, OH, 또는 CO2H를 포함해서는 안되고: W는 Cl, Br, F, I, C1-C4알킬, 니트로, CO2C1-C|4알킬, C1-C4알콕시, SCC1-C4알킬, CN, SO2C1-C4알킬, SO2NHR|7, NHSO2C1-C4알킬 또는 CnF2n+1이며, 여기에서 n은 1 내지 3이고, p는 0 내지 3이며, R7은 수소, C1-C4알킬 또는 (CH2)0-4페닐이고: R11은 COCH3또는 SO2CH3이다.
  13. 안지오텐신Ⅱ수용체 길항작용이 한 인자인 질병을 치료하기 위한 약제를 제조하는데 있어서 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염의 용도.
  14. 고혈압증을 치료하기 위한 약제를 제조하는데 있어서, 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는이의 약제학적으로 허용되는 염의 용도.
  15. 울형성 심부전증을 치료하기 위한 약제를 제조하는데 있어서, 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염의 용도.
  16. 신장병을 치료하기 위한 약제를 제조하는데 있어서 제1항에서 정의한 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염의 용도.
  17. ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900008739A 1989-06-14 1990-06-14 이미다졸릴-알켄산 및 이의 제조방법 및 약제학적 조성물 KR0165837B1 (ko)

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
US36607989A 1989-06-14 1989-06-14
US7/366079 1989-06-14
US366079 1989-06-14
US50641290A 1990-04-06 1990-04-06
US7/506412 1990-04-06
US506412 1990-04-06

Publications (2)

Publication Number Publication Date
KR910000658A true KR910000658A (ko) 1991-01-29
KR0165837B1 KR0165837B1 (ko) 1999-02-18

Family

ID=27003220

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019900008739A KR0165837B1 (ko) 1989-06-14 1990-06-14 이미다졸릴-알켄산 및 이의 제조방법 및 약제학적 조성물

Country Status (26)

Country Link
EP (2) EP0403159B1 (ko)
JP (1) JPH0768223B2 (ko)
KR (1) KR0165837B1 (ko)
CN (2) CN1027504C (ko)
AT (2) ATE190051T1 (ko)
CA (1) CA2018438C (ko)
CY (1) CY2232B1 (ko)
DE (3) DE69034103T2 (ko)
DK (2) DK0403159T3 (ko)
ES (2) ES2142789T3 (ko)
FI (1) FI102610B (ko)
GR (1) GR3033452T3 (ko)
HK (2) HK1012384A1 (ko)
HU (1) HU208537B (ko)
IE (2) IE902140A1 (ko)
IL (1) IL94698A (ko)
LU (1) LU90562I2 (ko)
MA (1) MA21896A1 (ko)
NL (1) NL300006I2 (ko)
NO (1) NO175977C (ko)
NZ (1) NZ233997A (ko)
PH (1) PH27592A (ko)
PL (3) PL165609B1 (ko)
PT (1) PT94377B (ko)
SG (1) SG52330A1 (ko)
ZW (1) ZW9490A1 (ko)

Families Citing this family (96)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5210079A (en) * 1988-01-07 1993-05-11 E. I. Du Pont De Nemours And Company Treatment of chronic renal failure with imidazole angiotensin-II receptor antagonists
US5185351A (en) * 1989-06-14 1993-02-09 Smithkline Beecham Corporation Imidazolyl-alkenoic acids useful as angiotensin II receptor antagonists
US5449682A (en) * 1990-02-13 1995-09-12 Merck & Co., Inc. Angiotensin II antagonists incorporating a substituted benzyl element
DE122010000024I1 (de) * 1990-02-19 2010-07-08 Novartis Ag Acylverbindungen
CA2085584C (en) * 1990-06-22 2003-02-11 David John Carini Treatment of chronic renal failure with imidazole angiotensin-ii receptor antagonists
NZ238688A (en) * 1990-06-28 1992-05-26 Smithkline Beecham Corp Substituted histidines: pharmaceutical compositions, preparation and uses thereof
NZ239161A (en) * 1990-07-31 1994-01-26 Smithkline Beecham Corp Substituted [1h-imidazol-5-yl] alkanoic acid derivatives; medicaments,
GB9027197D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
GB9027210D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
GB9027212D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
GB9027199D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
GB9027200D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
GB9027211D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
US6028091A (en) * 1990-12-14 2000-02-22 Smithkline Beecham Plc Medicament
GB9027201D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
US5656650A (en) * 1990-12-14 1997-08-12 Smithkline Beecham Corp. Angiotensin II receptor blocking compositions
GB9027198D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
US6034114A (en) * 1990-12-14 2000-03-07 Smithkline Beecham Plc Medicament
GB9027208D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
JP3214856B2 (ja) * 1990-12-14 2001-10-02 スミスクライン・ビーチャム・コーポレイション イミダゾリル−アルケン酸
DE10399008I1 (de) * 1990-12-14 2006-06-08 Smithkline Beecham Corp Angiotensin-II-Rezeptor blockierende Zusammensetzungen
GB9027209D0 (en) * 1990-12-14 1991-02-06 Smithkline Beecham Plc Medicaments
US6025380A (en) * 1990-12-14 2000-02-15 Smithkline Beecham Plc Medicament
US5236928A (en) * 1991-03-19 1993-08-17 Merck & Co., Inc. Imidazole derivatives bearing acidic functional groups at the 5-position, their compositions and methods of use as angiotensin II antagonists
EP0505098A1 (en) * 1991-03-19 1992-09-23 Merck & Co. Inc. Imidazole derivatives bearing acidic functional groups as angiotensin II antagonists
US5187179A (en) * 1991-03-22 1993-02-16 Merck & Co., Inc. Angiotensin II antagonists incorporating a substituted imidazo [1,2-b][1,2,4]triazole
US5128327A (en) * 1991-03-25 1992-07-07 Merck & Co., Inc. Angiotensin II antagonists incorporating a nitrogen containing six membered ring heterocycle
US5177074A (en) * 1991-03-26 1993-01-05 Merck & Co., Inc. Angiotensin ii antagonists incorporating a substituted thiophene or furan
US5252574A (en) * 1991-04-26 1993-10-12 Merck & Co., Inc. Angiotensin II antagonists incorporating a substituted thiophene or furan
US5198438A (en) * 1991-05-07 1993-03-30 Merck & Co., Inc. Angiotensin ii antagonists incorporating a substituted thiophene or furan
GB9110532D0 (en) * 1991-05-15 1991-07-03 Smithkline Beecham Corp Chemical compounds
US5447949A (en) * 1991-05-15 1995-09-05 Smithkline Beecham Corporation N-(heteroaryl) imidazolyl-alkenoic acids having angiotension II receptor antagonist activity
GB9110636D0 (en) * 1991-05-16 1991-07-03 Glaxo Group Ltd Chemical compounds
US5175164A (en) * 1991-06-05 1992-12-29 Merck & Co., Inc. Angiotensin ii antagonists incorporating a substituted indole or dihydroindole
DE4132633A1 (de) * 1991-10-01 1993-04-08 Bayer Ag Cyclisch substituierte imidazolyl-propensaeurederivate
DE4132631A1 (de) * 1991-10-01 1993-04-08 Bayer Ag Imidazolyl-propensaeurederivate
DE4132632A1 (de) * 1991-10-01 1993-04-08 Bayer Ag Substituierte imidazolyl-propensaeurederivate
GB9121463D0 (en) * 1991-10-10 1991-11-27 Smithkline Beecham Corp Medicament
US5322950A (en) * 1991-12-05 1994-06-21 Warner-Lambert Company Imidazole with angiotensin II antagonist properties
US5389661A (en) * 1991-12-05 1995-02-14 Warner-Lambert Company Imidazole and 1,2,4-triazole derivatives with angiotensin II antagonist properties
US5308853A (en) * 1991-12-20 1994-05-03 Warner-Lambert Company Substituted-5-methylidene hydantoins with AT1 receptor antagonist properties
US5240953A (en) * 1992-01-30 1993-08-31 Ortho Pharmaceutical Corporation Substituted triazoles as angiotensin ii inhibitors
FR2687674B1 (fr) * 1992-02-07 1995-05-19 Roussel Uclaf Nouveaux derives de la pyridone, leur procede de preparation, les nouveaux intermediaires obtenus, leur application a titre de medicaments et les compositions pharmaceutiques les renfermant.
DE4206042A1 (de) * 1992-02-27 1993-09-02 Bayer Ag Sulfonylbenzyl-substituierte imidazopyridine
DE4206043A1 (de) * 1992-02-27 1993-09-02 Bayer Ag Sulfonylbenzyl-substituierte imidazole
DE4206045A1 (de) * 1992-02-27 1993-09-02 Bayer Ag Sulfonylbenzyl substituierte pyridone
DE4206041A1 (de) * 1992-02-27 1993-09-02 Bayer Ag Sulfonylbenzyl-substituierte imidazolylpropensaeurederivate
US5364869A (en) * 1992-03-09 1994-11-15 Abbott Laboratories Heterocycle-substituted benzyaminopyridine angiotensin II receptor antagonists
FR2689508B1 (fr) * 1992-04-01 1994-06-17 Fournier Ind & Sante Derives de l'imidazole, leur procede de preparation et leur application en therapeutique.
DE4210787A1 (de) * 1992-04-01 1993-10-07 Bayer Ag Cycloalkyl- und Heterocyclyl substituierte Imidazolylpropensäurederivate
DE4212796A1 (de) * 1992-04-16 1993-10-21 Bayer Ag Propenoyl-imidazolderivate
DE4215588A1 (de) * 1992-05-12 1993-11-18 Bayer Ag Biphenylmethyl-substituierte Pyridone
DE4215587A1 (de) * 1992-05-12 1993-11-18 Bayer Ag Sulfonylbenzyl-substituierte Benzo- und Pyridopyridone
DE4319041A1 (de) * 1992-10-23 1994-04-28 Bayer Ag Trisubstituierte Biphenyle
EP0757685B1 (en) * 1994-04-29 2004-07-21 Pfizer Inc. Novel acyclic and cyclic amides as neurotransmitter release enhancers
US20030004202A1 (en) 1997-04-28 2003-01-02 Smithkline Beecham Corporation Endothelin receptor antagonists
JPH10505085A (ja) * 1994-09-02 1998-05-19 スミスクライン・ビーチャム・コーポレイション エンドセリン受容体拮抗薬
DE69624253T2 (de) * 1995-10-06 2003-08-07 Novartis Ag Ati-rezeptorantagonisten zur verhinderung und behandlung des postischemischen nervenversagens und zum schutze ischemischer nieren
JP2000502104A (ja) * 1995-12-21 2000-02-22 スミスクライン・ビーチャム・コーポレイション エンドセリン受容体アンタゴニスト
JP4369994B2 (ja) 1996-02-29 2009-11-25 ノバルティス アクチエンゲゼルシャフト アポトーシスの刺激のためのａｔ▲下１▼レセプターアンタゴニスト
AR011126A1 (es) 1997-02-14 2000-08-02 Smithkline Beecham Corp Procedimiento para preparar eprosartano y compuestos intermediarios.
JP2002520385A (ja) 1998-07-18 2002-07-09 バイエル アクチェンゲゼルシャフト イミドアミド誘導体
US6465502B1 (en) 1998-12-23 2002-10-15 Novartis Ag Additional therapeutic use
TR200200764T2 (tr) 1998-12-23 2002-07-22 Novartis Ag At-1 veya at-2 reseptörlerindeki artışın neden olduğu hastalıkların tedavisi için at-1 reseptör antagonisti veya at-2 reseptör modülatörünün kullanımı
CN101011390A (zh) 1999-01-26 2007-08-08 诺瓦提斯公司 血管紧张素ⅱ受体拮抗剂在治疗急性心肌梗塞中的应用
SE9903028D0 (sv) 1999-08-27 1999-08-27 Astra Ab New use
PE20020617A1 (es) 2000-08-22 2002-08-05 Novartis Ag Composicion que comprende un antagonista del receptor at1 y un potenciador de la secrecion de insulina o un sensibilizante a la insulina
US8168616B1 (en) 2000-11-17 2012-05-01 Novartis Ag Combination comprising a renin inhibitor and an angiotensin receptor inhibitor for hypertension
US7732162B2 (en) 2003-05-05 2010-06-08 Probiodrug Ag Inhibitors of glutaminyl cyclase for treating neurodegenerative diseases
US20060276523A1 (en) * 2003-07-31 2006-12-07 Nicoletta Almirante Nitoroxy derivatives of losartan, valsatan, candesartan, telmisartan, eprosartan and olmesartan as angiotensin-II receptor blockers for the treatment of cardiovascular diseases
GB0327839D0 (en) 2003-12-01 2003-12-31 Novartis Ag Organic compounds
GB0402262D0 (en) 2004-02-02 2004-03-10 Novartis Ag Process for the manufacture of organic compounds
TW200605867A (en) 2004-03-17 2006-02-16 Novartis Ag Use of organic compounds
JP2008515903A (ja) 2004-10-08 2008-05-15 ノバルティス アクチエンゲゼルシャフト 拡張機能障害または拡張期心不全の予防または処置のためのレニン阻害剤の使用
MX2007005129A (es) 2004-10-27 2007-09-11 Daiichi Sankyo Co Ltd Compuesto de benceno que tiene 2 o mas sustituyentes.
ZA200905537B (en) 2007-03-01 2010-10-27 Probiodrug Ag New use of glutaminyl cyclase inhibitors
JP5667440B2 (ja) 2007-04-18 2015-02-12 プロビオドルグ エージー グルタミニルシクラーゼ阻害剤としてのチオ尿素誘導体
US8969514B2 (en) 2007-06-04 2015-03-03 Synergy Pharmaceuticals, Inc. Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases
US20100120694A1 (en) 2008-06-04 2010-05-13 Synergy Pharmaceuticals, Inc. Agonists of Guanylate Cyclase Useful for the Treatment of Gastrointestinal Disorders, Inflammation, Cancer and Other Disorders
EP2527360B1 (en) 2007-06-04 2015-10-28 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders
RU2453536C2 (ru) * 2007-10-22 2012-06-20 Оркид Рисерч Лабораториз Лимитед Ингибиторы гистондезацетилазы
AR072477A1 (es) * 2008-07-11 2010-09-01 Solvay Pharm Bv Formulacion farmaceutica de eprosartan. uso.
ES2624828T3 (es) 2008-07-16 2017-07-17 Synergy Pharmaceuticals Inc. Agonistas de la guanilato ciclasa útiles para el tratamiento de trastornos gastrointestinales, inflamación, cáncer y otros
WO2011004384A2 (en) 2009-06-05 2011-01-13 Glochem Industries Limited Process for the preparation of eprosartan
US8486940B2 (en) 2009-09-11 2013-07-16 Probiodrug Ag Inhibitors
WO2011107530A2 (en) 2010-03-03 2011-09-09 Probiodrug Ag Novel inhibitors
KR101790806B1 (ko) 2010-03-10 2017-11-20 프로비오드룩 아게 글루타미닐 사이클라제(ｑｃ, ｅｃ 2.3.2.5)의 헤테로사이클릭 억제제
WO2011131748A2 (en) 2010-04-21 2011-10-27 Probiodrug Ag Novel inhibitors
US9616097B2 (en) 2010-09-15 2017-04-11 Synergy Pharmaceuticals, Inc. Formulations of guanylate cyclase C agonists and methods of use
ES2570167T3 (es) 2011-03-16 2016-05-17 Probiodrug Ag Derivados de benzimidazol como inhibidores de glutaminil ciclasa
WO2013090196A1 (en) 2011-12-15 2013-06-20 Takeda Pharmaceuticals U.S.A., Inc. Combinations of azilsartan and chlorthalidone for treating hypertension black patients
CN102584628B (zh) * 2011-12-30 2015-04-22 浙江外国语学院 一种n-羧甲基戊脒的合成方法
WO2014151206A1 (en) 2013-03-15 2014-09-25 Synergy Pharmaceuticals Inc. Agonists of guanylate cyclase and their uses
WO2014151200A2 (en) 2013-03-15 2014-09-25 Synergy Pharmaceuticals Inc. Compositions useful for the treatment of gastrointestinal disorders
US10011637B2 (en) 2013-06-05 2018-07-03 Synergy Pharmaceuticals, Inc. Ultra-pure agonists of guanylate cyclase C, method of making and using same
DK3461819T3 (da) 2017-09-29 2020-08-10 Probiodrug Ag Inhibitorer af glutaminylcyklase

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS5671073A (en) * 1979-11-12 1981-06-13 Takeda Chem Ind Ltd Imidazole derivative
JPS5671074A (en) * 1979-11-12 1981-06-13 Takeda Chem Ind Ltd 1,2-disubstituted-4-halogenoimidazole-5-acetic acid derivative
JPS58157768A (ja) * 1982-03-16 1983-09-19 Takeda Chem Ind Ltd ４−クロロ−２−フエニルイミダゾ−ル−５−酢酸誘導体
US4668794A (en) * 1985-05-22 1987-05-26 Sandoz Pharm. Corp. Intermediate imidazole acrolein analogs
CA1334092C (en) * 1986-07-11 1995-01-24 David John Carini Angiotensin ii receptor blocking imidazoles
US4835154A (en) * 1987-06-01 1989-05-30 Smithkline Beckman Corporation 1-aralykyl-5-piperazinylmethyl-2-mercaptoimidazoles and 2-alkylthioimidazoles and their use as dopamine-βhydroxylase inhibitors
US4798843A (en) * 1987-07-09 1989-01-17 Smithkline Beckman Corporation 2-mercaproimidazole dopamine-β-hydroxylase inhibitors
CA1338238C (en) * 1988-01-07 1996-04-09 David John Carini Angiotensin ii receptor blocking imidazoles and combinations thereof with diuretics and nsaids

Also Published As

Publication number Publication date
NL300006I1 (nl) 2000-07-03
CN1079649A (zh) 1993-12-22
SG52330A1 (en) 1998-09-28
LU90562I2 (fr) 2000-06-05
CA2018438A1 (en) 1990-12-14
DE69034103D1 (de) 2003-10-30
ATE190051T1 (de) 2000-03-15
CN1048038A (zh) 1990-12-26
EP0403159A2 (en) 1990-12-19
PT94377A (pt) 1991-03-20
FI102610B1 (fi) 1999-01-15
NZ233997A (en) 1991-04-26
ATE250587T1 (de) 2003-10-15
NL300006I2 (nl) 2000-10-02
EP0955294B1 (en) 2003-09-24
NO902632D0 (no) 1990-06-13
IE20000297A1 (en) 2000-12-13
DK0403159T3 (da) 2000-08-14
PH27592A (en) 1993-08-31
EP0955294A2 (en) 1999-11-10
HU208537B (en) 1993-11-29
DE69034103T2 (de) 2004-07-15
AU5690190A (en) 1991-01-10
NO175977C (no) 1995-01-11
IE902140L (en) 1990-12-14
DK0955294T3 (da) 2004-02-02
PL166722B1 (pl) 1995-06-30
HK1025315A1 (en) 2000-11-10
PL285591A1 (en) 1991-03-25
EP0403159A3 (en) 1991-12-27
ES2142789T3 (es) 2000-05-01
HU903847D0 (en) 1990-11-28
GR3033452T3 (en) 2000-09-29
IE902140A1 (en) 1991-01-02
FI902970A0 (fi) 1990-06-13
DE69033469D1 (de) 2000-04-06
DE69033469T2 (de) 2000-09-07
FI102610B (fi) 1999-01-15
IL94698A0 (en) 1991-04-15
HK1012384A1 (en) 1999-07-30
CY2232B1 (en) 2003-04-18
NO902632L (no) 1990-12-17
EP0403159B1 (en) 2000-03-01
AU633322B2 (en) 1993-01-28
PL166669B1 (pl) 1995-06-30
CA2018438C (en) 2000-08-08
PT94377B (pt) 1997-02-28
JPH0768223B2 (ja) 1995-07-26
IL94698A (en) 1994-07-31
CN1048159C (zh) 2000-01-12
NO175977B (no) 1994-10-03
EP0955294A3 (en) 2000-04-19
PL165609B1 (pl) 1995-01-31
JPH03115278A (ja) 1991-05-16
DE10075018I1 (de) 2000-09-21
ES2207091T3 (es) 2004-05-16
MA21896A1 (fr) 1991-04-01
HUT55011A (en) 1991-04-29
ZW9490A1 (en) 1990-10-31
KR0165837B1 (ko) 1999-02-18
CN1027504C (zh) 1995-01-25
DE10075018I2 (de) 2001-08-09

Similar Documents

Publication Publication Date Title
KR910000658A (ko) 이미다졸릴- 알케노산
KR910000659A (ko) 이미다졸릴-알케노산
KR910007918A (ko) 치환된5-[(테트라졸릴)알케닐]이미다졸
KR900701782A (ko) 퀴누클리딘 치료제
KR920014805A (ko) 퀴나졸리논 화합물, 그의 제약학적 조성물 및 그의 제조방법
KR960703858A (ko) 물질 p 길항제로서의 퍼히드로이소인돌 유도체(perhydroisoindole derivatives as substance p antagonists)
CA2394086A1 (fr) Derives de 4-aminopiperidine et leur utilisation en tant que medicament
BR9104181A (pt) Composto
KR910009659A (ko) 신규한 이소인돌론 유도체, 그들의 제조 방법 및 그들을 함유한 제약학적 조성물
KR910011798A (ko) 치환된 5-(알킬)카복스아미드 이미다졸
KR880006241A (ko) 9-사이클로펜틸- 치환된 아데닌 유도체
KR900011760A (ko) 신규한 벤조 피란 유도체, 그 제조 및 상기 유도체를 함유하는 제약학적 조성물
KR880009936A (ko) 피리딘-2,4-및-2,5-디카복실산 아미드, 그의 제조방법 및 용도
RU94030476A (ru) Производные пиперазина, способ их получения и фармацевтическая композиция
KR910009669A (ko) 치환된 n-(이미다졸릴)알킬 알라닌 유도체
KR930701411A (ko) 치환된 히스티딘
ZA200402806B (en) Alkyl ether derivatives or their salts
KR900011728A (ko) 5-리폭시게나제 억제제로서의 치환된 인돌, 벤조푸란 및 벤조티오펜 유도체
JP2000336063A (ja) 新規化合物およびその医薬用途
JPS63295540A (ja) Ｚ−２−アシルアミノ−３−モノ置換プロペノエート
US4619944A (en) Antihypertensive compounds
ATE37872T1 (de) Phenylinden-derivate, ihre salze, und verfahren zu ihrer herstellung.
US5118703A (en) Prodrugs of antiinflammatory 3-acyl-2-oxindole-1-carboxamides
KR850001170A (ko) 치환된 비닐 유도체의 제조방법
KR880005138A (ko) 신규 화합물들

Legal Events

Date Code Title Description
A201 Request for examination
E902 Notification of reason for refusal
E701 Decision to grant or registration of patent right
GRNT Written decision to grant
A101 Application to extend term of patent right by permit
A101 Application to extend term of patent right by permit
FPAY Annual fee payment

Payment date: 20120830

Year of fee payment: 15

FPAY Annual fee payment

Payment date: 20130329

Year of fee payment: 16

EXPY Expiration of term