KR910004600A - 류코트리엔의 생합성 억제제로서의 (퀴놀린-2-일메톡시)인돌 - Google Patents

류코트리엔의 생합성 억제제로서의 (퀴놀린-2-일메톡시)인돌 Download PDF

Info

Publication number
KR910004600A
KR910004600A KR1019900012848A KR900012848A KR910004600A KR 910004600 A KR910004600 A KR 910004600A KR 1019900012848 A KR1019900012848 A KR 1019900012848A KR 900012848 A KR900012848 A KR 900012848A KR 910004600 A KR910004600 A KR 910004600A
Authority
KR
South Korea
Prior art keywords
ylmethoxy
indol
quinolin
chlorobenzyl
dimethylpropanoic acid
Prior art date
Application number
KR1019900012848A
Other languages
English (en)
Inventor
프라지트 페트피분
포틴 리전
에이치. 허친슨 존
엘. 벨리 미쉘
리거 서지
질러드 존
프레네트 리차드
Original Assignee
제임스 에프. 노튼
머크 프로스트 캐나다, 인코포레이티드
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 제임스 에프. 노튼, 머크 프로스트 캐나다, 인코포레이티드 filed Critical 제임스 에프. 노튼
Publication of KR910004600A publication Critical patent/KR910004600A/ko

Links

Classifications

    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
    • A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P11/00—Drugs for disorders of the respiratory system
    • A61P11/08—Bronchodilators
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A61P25/04—Centrally acting analgesics, e.g. opioids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Veterinary Medicine (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Pain & Pain Management (AREA)
  • Pulmonology (AREA)
  • Neurology (AREA)
  • Rheumatology (AREA)
  • Biomedical Technology (AREA)
  • Immunology (AREA)
  • Neurosurgery (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Indole Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Peptides Or Proteins (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

내용 없음.

Description

류코트리엔의 생합성 억제제로서의 (퀴놀린-2-일메톡시)인돌
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (10)

  1. 일반식(I)의 화합물 및 그의 약제학적으로 허용되는 염.
    상기식에서, R1, R2, R3, R4및 R10은 각기 독립적으로 수소, 할로겐, 저급 알킬, 저급 알케닐, 저급 알키닐, -CF3, -CN, -NO2, -N3, -C(OH)R11R11, -CO2R12, -SR14, -S(O)R14-S(O)2R14, -S(O)2R15R15, -OR15, -NR15R15, -C(O)R16또는 -(CH2)tR21이며; R5는 수소, -CH3, -CF3, -C(O)H, -X1, -R6또는 X2-R7이고; R6및 R9는 각기 독립적으로 알킬, -(CH2)uPh(R10)2또는 -(CH2)uTH(R10)2이며 ; R7은 -CF3또는 R6이고; R8은 수소 또는 X3-R9이며; 각각의 R11은 독립적으로 수소 또는 저급 알킬이거나, 동일 탄소원자상의 2개의 R11은 결합하여 탄소수 3 내지 6의 사이클로알킬 환을 형성하고; R12는 수소, 저급 알킬 또는 -CH2R21이며; R13은 저급 알킬 또는 -(CH2)rR21이고; R14는 -CF3또는 R13이며 ; R15는 수소, -C(O)R16또는 R13이거나, 동일 질소상에 존재하는 2개의 R15는 결합하여, O, S 및 N중에서 선택된 2개 이하의 헤테로원자를 함유하는 4 내지 6원의 모노사이클릭 헤테로사이클릭 환을 형성할 수 있으며; R16은 수소, -CF3, 저급 알킬, 저급 알케닐, 저급 알키닐 또는 -(CH2)rR21이고; R17은 -(CH2)s-C (R18R18)-(CH2)s-R19또는 -CH2C (O)NR15R15이며 ; R18은 수소 또는 저급 알킬이고; R19는 a) 3 내지 9개의 핵 탄소원자 및 N, S 및 O중에서 선택된 1또는 2개의 핵 헤테로원자를 함유하는 모노사이클릭 또는 비사이클릭 헤테로사이클릭환 (여기에서 헤테로사이클릭 래디칼중의 각 환은 5 또는 6개의 원자로 형성된다), 또는 b) 래디칼 W-R20이며 ; R20은 알킬 또는 -C(O)R23이고; R21은 1 또는 2개의 R22그룹으로 치환된 페닐이며; R22는 수소, 할로겐, 저급 알킬, 저급 알콕시, 저급 알킬티오, 저급 알킬설포닐, 저급 알킬카보닐, -CF3, -CN, -NO2또는 -N3이고; R23은 알킬, 사이클로알킬, 또는모노사이클릭 모노 헤테로사이클릭 환이며; R24는 표준 아미노산의 잔기 구조이거나, 동일 N상에 결합된 R18과 R24는 폐환되어 프롤린 잔기를 형성할 수 있으며; m은 0 내지 1이고; n은 0내지 3이며; p는 m이 1이면 1 내지 3이고; p는 m이 0이면 0 내지 3이며; r은 0 내지 2이고; s는 0 내지 3이며; t는 0 내지 2이고; u는 0 내지 3이며; v는 0 또는 1이고; w는 S, S 또는 NR15이며; X1은 O 또는 NR15이고; X2는 C(O), CR11R11, S, S(O) 또는 S(O)2이며; X3는 C(O), CR11R11, S(O)2또는 결합이고; Y는 X1또는 X2이며 ; Q는 -CO2R12, -C(O)NHS(O)2R14, -NHS(O)2R14, -S(O)2NHR15-C(O)NR15R15, -CO2R17, -C(O)NR18R24, -CH2OH, 또는 1H- 또는 2H-테트라졸-5-일이다.
  2. 제1항에 있어서, 치환체가 다음과 같이 정의되는 일반식(Ic)의 화합물.
  3. 제1항에 있어서, 일반식(Id)의 화합물.
    상기식에서, R5는 제1항에서 정의한 바와 같다.
  4. 제1항에 있어서 치환체 R5가 수소, -Me, -S-t-Bu, -SPh, -S(O)2Ph, -S(O)Ph, C(O)Ph, -CH2Ph, -C(O)CH2-t-Bu, -O-i-Pr, -C(O)-CF3, -S(O)2-t-Bu, -S(O)-t-Bu, -C(O)Ph-4-t-Bu, -C(O)Ph-4-Cl, t-Bu, -C(O)Me, -C(O)-c-Pr, -C(O)CH2CH2-c-C5H9, -C(O)CH2CH(Me)2, -C(O)Et, -C(O)CH(Me)2, -C(O)C(Me)3, -C(O)CH2Ph, -C(Me)2Pr, -C(Me)2Et, -CH(Me)2, -c-Pr, -(1-Me)-c-Pr, -c-C5H9, -c-C6H11, -C(Me)2Ph, -C(Me)2Ph-4-Cl, -1-Ad, -CH2-1-Ad 또는 -CH2CH2-t-Bu 인 일반식(Id)의 화합물.
  5. 제1항에 있어서, 3-[N-(p-클로로벤질)-3-(±-부틸티오)-5-(퀴놀린-2-일 메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-메틸-5-(퀴놀린-2-일 메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-±-부틸티오벤질)-3-(±-부틸티오)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-(페닐티오)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-(페닐설포닐)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산 N-옥사이드; 3-[N-(p-클로로벤질)-3-(페닐설포닐)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-(페닐설피닐)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-벤조일-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-벤질-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 2-[N-(p-클로로벤질)-3-(±-부틸티오)-5-(퀴놀린-2-일메톡시)인돌-2-일]에톡시에타노산; 3-[N-(p-클로로벤질)-3-(3,3-디메틸-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-(±-부틸티오)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2-메틸프로파노산; 3-[N-(p-클로로벤질)-3-메틸-5-(6,7-디클로로퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-3-메틸-5-(7-클로로퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-4-알릴-5-(7-클로로퀴놀린-2-일메톡시)-3-(±-부틸티오)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-4-알릴-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-6-(퀴놀린-2-일메톡시)-3-(±-부틸티오)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-4-(퀴놀린-2-일메톡시)-3-(±-부틸티오)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤질)-7-(퀴놀린-2-일메톡시)-3-(±-부틸티오)인돌-2-일]-2,2-디메틸프로파노산; 2-[2-[N-(p-클로로벤질)-3-(±-부틸티오)-5-(퀴놀린-2-일메톡시)인돌-2-일]에톡시]프로파노산; 3-[N-(p-클로로벤질)-4-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(p-클로로벤조일)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-메틸-3-(p-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-이소프로폭시-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(±-부틸티오)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-트리플루오로아세틸-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2-메틸프로파노산; 3-[3-(3,3-디메틸-1-옥소-1-부틸-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-트리플루오로메틸벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-벤질-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(3-메톡시벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-알릴-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-메톡시벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-메틸-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[3-(4-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(페닐설포닐)-3-(4-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-벤질-3-(4-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(±-부틸설포닐)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(±-부틸설포닐)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-알릴-3-(4-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(n-프로필)-3-(4-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-에틸-3-(4-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(4-±-부틸벤조인)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(4-클로로벤조일)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(1,1-디메틸에틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-아세틸-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-사이클로프로판카보닐-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(3-사이클로펜틸프로파노일)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(3-메틸부타노일)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-프로파노일-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,3-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(2-메틸프로파노일)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-트리메틸아세틸-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-페닐아세틸-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-플루오로벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-브로모벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-요오도벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(1,1-디메틸부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(1,1-디메틸프로필)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(3-플루오로벤질)-3-(1-메틸에틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(1,1-디메틸프로필)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-사이클로프로필-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(1-메틸-1-사이클로프로필)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-사이클로펜틸-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-사이클로헥실-5-(퀴놀린-2-일메톡시)인돌-2-일)-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(α,α-디메틸벤질)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(2-{4-클로로-α,α-디메틸벤질)-5-(퀴놀린-2-일메톡시)인돌-2-인)-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(1-아다만틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-((1-아다만틸)메틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(1,1-디메틸에틸)-3-(4-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(1,1-디메틸프로필)-3-(4-클로로벤질)-6-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 3-[N-(4-클로로벤질)-3-(3,3-디메틸-1-옥소-1-부틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노산; 메틸 3-[N-(4-클로로벤질)-3,6-비스(아세틸)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노에이트; 또는 메틸 3-[N-(4-클로로벤질)-3,6-비스(사이클로프로판카보닐)-5-(퀴놀린-2-일메톡시)인돌-2-일]-2,2-디메틸프로파노에이트인 화합물.
  6. 치료학적 유효량의 제1항의 화합물 및 약제학적으로 허용되는 담체를 함유하는 약제학적 조성물.
  7. 제6항에 있어서, 추가로 비스테로이드성 소염제, 말초성 진통제, 사이클로옥시게나제 억제제, 류코트리엔 길항제, 류코르리엔 생합성 억제제. H2-수용제 길항제, 항히스타민제, 프로스타글란딘 길항제, 트롬복산 길항제, 트롬복산 합성 효소 억제제 및 ACF 길항제로 구성된 그룹중에서 선택된 제2의 활성성분의 유효량을 함유하는 약제학적 조성물.
  8. 포유 동물에게 유효량의 제1항의 화합물을 투여함을 특징으로 하여, 포유 동물에서 SRS-A 또는 류코트리엔의 합성, 작용 또는 방출을 억제하는 방법.
  9. 천식의 치료를 요하는 포유동물에게 치료학적 유효량의 제1항의 화합물을 투여함을 특징으로 하여, 포유동물에서 천식을 치료하는 방법.
  10. 눈의 염증성 질환의 치료를 요하는 포유 동물에게 치료학적 유효량의 제1항의 화합물을 투여함을 특징으로 하여, 포유 동물에서 눈의 염증성 질환을 치료하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900012848A 1989-08-22 1990-08-21 류코트리엔의 생합성 억제제로서의 (퀴놀린-2-일메톡시)인돌 KR910004600A (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US39714489A 1989-08-22 1989-08-22
US397144 1989-08-22
US55230090A 1990-07-18 1990-07-18
US552,300 1990-07-18

Publications (1)

Publication Number Publication Date
KR910004600A true KR910004600A (ko) 1991-03-29

Family

ID=27015763

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019900012848A KR910004600A (ko) 1989-08-22 1990-08-21 류코트리엔의 생합성 억제제로서의 (퀴놀린-2-일메톡시)인돌

Country Status (13)

Country Link
EP (1) EP0419049B1 (ko)
JP (1) JPH0786101B2 (ko)
KR (1) KR910004600A (ko)
AT (1) ATE121085T1 (ko)
AU (1) AU650185B2 (ko)
CA (1) CA2023340C (ko)
DE (1) DE69018553T2 (ko)
FI (1) FI904132A0 (ko)
IE (1) IE903022A1 (ko)
IL (1) IL95371A (ko)
NO (1) NO176606C (ko)
NZ (1) NZ234883A (ko)
PT (1) PT95055A (ko)

Families Citing this family (77)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5272145A (en) * 1989-08-22 1993-12-21 Merck Frosst Canada, Inc. (Quinolin-2-ylmethoxy)indoles as inhibitors of the biosynthesis of leukotrienes
US5204344A (en) * 1989-08-22 1993-04-20 Merck Frosst Canada, Inc. (Quinolin-2-ylmethoxy)indoles as inhibitors of the biosynthesis of leukotrienes
US5252585A (en) * 1992-02-03 1993-10-12 Merck Frosst Canada, Inc. Fluorinated quinoline indoles as inhibitors of the biosynthesis of leukotrienes
US5095031A (en) * 1990-08-20 1992-03-10 Abbott Laboratories Indole derivatives which inhibit leukotriene biosynthesis
JPH0764841B2 (ja) * 1990-10-03 1995-07-12 ファイザー製薬株式会社 インドール誘導体およびその用途
US5202321A (en) * 1991-06-13 1993-04-13 Merck Frosst Canada, Inc. Thiopyrano[2,3,4-c,d]indoles as inhibitors of leukotriene biosynthesis
CA2079374C (en) * 1991-09-30 2003-08-05 Merck Frosst Canada Incorporated (bicyclic-azaarylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5389650A (en) * 1991-09-30 1995-02-14 Merck Frosst Canada, Inc. (Azaarylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5308850A (en) * 1991-09-30 1994-05-03 Merck Frosst Canada, Inc. (Bicyclic-hetero-arylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5190968A (en) * 1991-09-30 1993-03-02 Merck Frosst Canada, Inc. (Polycyclic-arylmethoxy) indoles as inhibitors of leukotriene biosynthesis
US5290798A (en) * 1991-09-30 1994-03-01 Merck Frosst Canada, Inc. (hetero-arylmethoxy)indoles as inhibitors of leukotriene biosynthesis
US5321033A (en) * 1991-11-15 1994-06-14 Merck Frosst Canada, Inc. Amorphous (quinolin-2-ylmethoxy)indole compounds useful for treating inflammatory diseases
US5254567A (en) * 1991-11-15 1993-10-19 Merck Frosst Canada, Inc. Amorphous (quinolin-2-ylmethoxy)indole compounds which have useful pharmaceutical utility
EP0542355A1 (en) * 1991-11-15 1993-05-19 Merck Frosst Canada Inc. Amorphous (Quinolin-2-ylmethoxy)indoles as leukotriene antagonists
US5254541A (en) * 1991-11-15 1993-10-19 Merck Frosst Canada, Inc. (Quinolin-2-ylmethoxy)indole/cyclodextrin complex
WO1993016069A1 (en) * 1992-02-13 1993-08-19 Merck Frosst Canada Inc. (azaaromaticalkoxy)indoles as inhibitors of leukotriene biosynthesis
US5274096A (en) * 1992-03-17 1993-12-28 Merck & Co., Inc. Hydrazine synthesis
US5334719A (en) * 1992-06-17 1994-08-02 Merck Frosst Canada, Inc. Bicyclic(azaaromatic)indoles as inhibitors of leukotriene bisynthesis
CA2136241C (en) * 1992-06-22 2004-01-27 Richard Frenette Fluorinated quinoline indoles as inhibitors of the biosynthesis of leukotrienes
US5314900A (en) * 1992-11-19 1994-05-24 Merck Frosst Canada, Inc. Aryl thiopyrano[2,3,4-C,D]indoles as inhibitors of leukotriene biosynthesis
US5288743A (en) * 1992-11-20 1994-02-22 Abbott Laboratories Indole carboxylate derivatives which inhibit leukotriene biosynthesis
US5374635A (en) * 1993-03-29 1994-12-20 Merck Frosst Canada, Inc. Furo[3,2-b]pyridines and thieno[3,2-b]pyridines as inhibitors of leukotriene biosynthesis
US5399699A (en) * 1994-01-24 1995-03-21 Abbott Laboratories Indole iminooxy derivatives which inhibit leukotriene biosynthesis
CN1067054C (zh) 1994-04-01 2001-06-13 伊莱利利公司 1H-吲哚-3-乙醛酰胺sPLA2抑制剂
US5859031A (en) * 1995-06-07 1999-01-12 Gpi Nil Holdings, Inc. Small molecule inhibitors of rotamase enzyme activity
US5801197A (en) * 1995-10-31 1998-09-01 Gpi Nil Holdings, Inc. Rotamase enzyme activity inhibitors
US6218424B1 (en) 1996-09-25 2001-04-17 Gpi Nil Holdings, Inc. Heterocyclic ketone and thioester compounds and uses
US5786378A (en) * 1996-09-25 1998-07-28 Gpi Nil Holdings, Inc. Heterocyclic thioesters
US5801187A (en) * 1996-09-25 1998-09-01 Gpi-Nil Holdings, Inc. Heterocyclic esters and amides
US6187784B1 (en) 1998-06-03 2001-02-13 Gpi Nil Holdings, Inc. Pipecolic acid derivative hair growth compositions and uses
US5945441A (en) 1997-06-04 1999-08-31 Gpi Nil Holdings, Inc. Pyrrolidine carboxylate hair revitalizing agents
US6271244B1 (en) 1998-06-03 2001-08-07 Gpi Nil Holdings, Inc. N-linked urea or carbamate of heterocyclic thioester hair growth compositions and uses
US6187796B1 (en) 1998-06-03 2001-02-13 Gpi Nil Holdings, Inc. Sulfone hair growth compositions and uses
US6274602B1 (en) 1998-06-03 2001-08-14 Gpi Nil Holdings, Inc. Heterocyclic thioester and ketone hair growth compositions and uses
US20010049381A1 (en) 1997-06-04 2001-12-06 Gpl Nil Holdings, Inc., Pyrrolidine derivative hair growth compositions and uses
GB9716657D0 (en) 1997-08-07 1997-10-15 Zeneca Ltd Chemical compounds
GB9803226D0 (en) 1998-02-17 1998-04-08 Zeneca Ltd Chemical compounds
US6429215B1 (en) 1998-06-03 2002-08-06 Gpi Nil Holdings, Inc. N-oxide of heterocyclic ester, amide, thioester, or ketone hair growth compositions and uses
AU1708099A (en) 1998-06-03 1999-12-20 Amgen, Inc. N-linked sulfonamides of n-heterocyclic carboxylic acids or carboxylic acid isosteres
AU770459B2 (en) 1998-06-03 2004-02-19 Gpi Nil Holdings, Inc. Heterocyclic ester and amide hair growth compositions and uses
US6172087B1 (en) 1998-06-03 2001-01-09 Gpi Nil Holding, Inc. N-oxide of heterocyclic ester, amide, thioester, or ketone hair growth compositions and uses
US6399648B1 (en) 1998-08-14 2002-06-04 Gpi Nil Holdings, Inc. N-oxides of heterocyclic ester, amide, thioester, or ketone for vision and memory disorders
US6335348B1 (en) 1998-08-14 2002-01-01 Gpi Nil Holdings, Inc. Nitrogen-containing linear and azepinyl/ compositions and uses for vision and memory disorders
US6339101B1 (en) 1998-08-14 2002-01-15 Gpi Nil Holdings, Inc. N-linked sulfonamides of N-heterocyclic carboxylic acids or isosteres for vision and memory disorders
US6384056B1 (en) 1998-08-14 2002-05-07 Gpi Nil Holdings, Inc. Heterocyclic thioesters or ketones for vision and memory disorders
US6506788B1 (en) 1998-08-14 2003-01-14 Gpi Nil Holdings, Inc. N-linked urea or carbamate of heterocyclic thioesters for vision and memory disorders
US7338976B1 (en) 1998-08-14 2008-03-04 Gpi Nil Holdings, Inc. Heterocyclic esters or amides for vision and memory disorders
US6218423B1 (en) 1998-08-14 2001-04-17 Gpi Nil Holdings, Inc. Pyrrolidine derivatives for vision and memory disorders
US6395758B1 (en) 1998-08-14 2002-05-28 Gpi Nil Holdings, Inc. Small molecule carbamates or ureas for vision and memory disorders
US6376517B1 (en) 1998-08-14 2002-04-23 Gpi Nil Holdings, Inc. Pipecolic acid derivatives for vision and memory disorders
US6337340B1 (en) 1998-08-14 2002-01-08 Gpi Nil Holdings, Inc. Carboxylic acids and isosteres of heterocyclic ring compounds having multiple heteroatoms for vision and memory disorders
US6333340B1 (en) 1998-08-14 2001-12-25 Gpi Nil Holdings, Inc. Small molecule sulfonamides for vision and memory disorders
US6462072B1 (en) 1998-09-21 2002-10-08 Gpi Nil Holdings, Inc. Cyclic ester or amide derivatives
GB9902459D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
GB9902452D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
GB9902455D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
GB9902453D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
GB9902461D0 (en) 1999-02-05 1999-03-24 Zeneca Ltd Chemical compounds
GB0000625D0 (en) 2000-01-13 2000-03-01 Zeneca Ltd Chemical compounds
ES2211315B1 (es) * 2002-11-12 2005-10-16 Almirall Prodesfarma, S.A. Nuevos compuestos triciclicos.
CA2526730A1 (en) 2003-05-30 2004-12-09 Ranbaxy Laboratories Limited Substituted pyrrole derivatives
BRPI0413330A (pt) 2003-08-29 2006-10-10 Ranbaxy Lab Ltd inibidores de fosfodiesterase do tipo iv, composição farmacêutica contendo os mesmos e processo para sua preparação
US8158362B2 (en) 2005-03-30 2012-04-17 Decode Genetics Ehf. Methods of diagnosing susceptibility to myocardial infarction and screening for an LTA4H haplotype
EP1934219A1 (en) 2005-09-16 2008-06-25 Ranbaxy Laboratories Limited Substituted pyrazolo [3,4-b] pyridines as phosphodiesterase inhibitors
US7405302B2 (en) * 2005-10-11 2008-07-29 Amira Pharmaceuticals, Inc. 5-lipoxygenase-activating protein (FLAP) inhibitors
US7977359B2 (en) 2005-11-04 2011-07-12 Amira Pharmaceuticals, Inc. 5-lipdxygenase-activating protein (FLAP) inhibitors
US8399666B2 (en) 2005-11-04 2013-03-19 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
GB2431927B (en) * 2005-11-04 2010-03-17 Amira Pharmaceuticals Inc 5-Lipoxygenase-activating protein (FLAP) inhibitors
SG166829A1 (en) 2005-11-08 2010-12-29 Ranbaxy Lab Ltd Process for (3r, 5r)-7-[2-(4-fluorophenyl)-5-isopropyl-3-phenyl-4- [(4-hydroxy methyl phenyl amino) carbonyl]-pyrrol-1-yl]-3, 5-dihydroxy-heptanoic acid hemi calcium salt
WO2008055808A1 (en) 2006-11-09 2008-05-15 F. Hoffmann-La Roche Ag Indole and benzofuran 2-carboxamide derivatives
EP1958947A1 (en) 2007-02-15 2008-08-20 Ranbaxy Laboratories Limited Inhibitors of phosphodiesterase type 4
NZ579645A (en) 2007-03-14 2012-01-12 Ranbaxy Lab Ltd Pyrazolo (3, 4-b) pyridine derivatives as phosphodiesterase inhibitors
TW200920369A (en) 2007-10-26 2009-05-16 Amira Pharmaceuticals Inc 5-lipoxygenase activating protein (flap) inhibitor
EP2285803A4 (en) 2008-05-23 2011-10-05 Amira Pharmaceuticals Inc Inhibitor of 5-Lipoxygenase Activating Protein
US8546431B2 (en) 2008-10-01 2013-10-01 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
WO2016149126A1 (en) 2015-03-13 2016-09-22 The Board Of Trustees Of The Leland Stanford Junior University Ltb4 inhibition to prevent and treat human lymphedema
CN109535060B (zh) * 2018-12-20 2022-03-25 苏州麦迪耐斯医药科技有限公司 一种刺猬通路抑制剂及其制备方法和应用

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA824343B (en) * 1981-07-01 1983-04-27 Upjohn Co Pyridinyl- and imidazolyl-benzofurane and benzothiophenes
CA1241660A (en) * 1984-06-25 1988-09-06 Yvan Guindon Indole-2-alkanoic acids
US4767865A (en) * 1985-10-30 1988-08-30 The Upjohn Company 3'-pyridinylalkylinden- and 3'-pyridinylalkylindol-2-carboxylic acids and analogs
IL84796A (en) * 1986-12-17 1992-03-29 Merck Frosst Canada Inc Substituted n-benzyl-indoles and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
IL95371A0 (en) 1991-06-30
AU6121190A (en) 1991-02-28
EP0419049B1 (en) 1995-04-12
AU650185B2 (en) 1994-06-09
NO903678D0 (no) 1990-08-21
JPH03163075A (ja) 1991-07-15
PT95055A (pt) 1991-04-18
JPH0786101B2 (ja) 1995-09-20
IE903022A1 (en) 1991-02-27
CA2023340A1 (en) 1991-02-23
EP0419049A1 (en) 1991-03-27
DE69018553D1 (de) 1995-05-18
AU3012692A (en) 1993-02-11
CA2023340C (en) 2000-07-11
NO903678L (no) 1991-03-21
AU628212B2 (en) 1992-09-10
IL95371A (en) 1994-08-26
NZ234883A (en) 1995-01-27
NO176606C (no) 1995-05-03
FI904132A0 (fi) 1990-08-21
DE69018553T2 (de) 1995-10-19
ATE121085T1 (de) 1995-04-15
NO176606B (no) 1995-01-23

Similar Documents

Publication Publication Date Title
KR910004600A (ko) 류코트리엔의 생합성 억제제로서의 (퀴놀린-2-일메톡시)인돌
KR880007460A (ko) 3-헤테로-치환된-n-벤질-인돌
AU2004287245B2 (en) Use of CRTH2 antagonist compounds in therapy
KR950701630A (ko) 안지오텐신 Ⅱ 길항 물질로서의 치환된 인돌 및 아자인돌(Substituted Indoles and Azaindoles as Angiotensin Ⅱ Antagonists)
CA2303594C (en) Compounds for treating and preventing diabetic complications
KR920008006A (ko) 류코트리엔 길항제로서의 불포화 하이드록시 알킬퀴놀린산
US5300506A (en) Indolylalkyl derivatives of pyrimidinylpiperazine for treating vascular headache
US20080199454A1 (en) Caspase inhibitor prodrugs
SK284408B6 (sk) Chemické zlúčeniny s protizápalovou aktivitou obsahujúce indolovú skupinu, spôsob ich prípravy, použitie a farmaceutické kompozície, ktoré ich obsahujú
PE20070336A1 (es) Compuestos de indolina como agonistas de receptores adrenergicos alfa2c funcionalmente selectivos
JP2008535908A (ja) Ｎｏｓ阻害活性を有する置換インドール化合物
JP2009508872A (ja) カルバゾール誘導体
KR910002795A (ko) 2- (아미노아릴) 인돌 및 인돌린, 이의 제조방법 및 약제로서의 용도
KR890008104A (ko) 디아릴스티릴퀴놀린 이산
FI945319A (fi) Substituoidut indolit ja atsaindolit angiotensiini II:n antagonisteina
PE20000329A1 (es) Derivados de indol y composiciones farmaceuticas que los contienen
KR920016423A (ko) 루코트리엔 길항제로서의 퀴놀린-함유 케토산
KR920019779A (ko) 치환된 인돌의 n-이미다졸릴 유도체
US4006238A (en) Use of 2-(hydroxyalkyl)-1H-benz[de]isoquinoline-1,3(2H)-diones as anti-allergy agents
US5618816A (en) Antimigraine 1,2,5-thiadiazole derivatives of indolylalkyl-pyridnyl and pyrimidinylpiperazines
KR950002760A (ko) 안압 강하제
CA2281050A1 (en) Nitric oxide releasing oxindole prodrugs for analgesic, anti-inflammatory and disease-modifying use
EP1132087A1 (en) Remedies for polycystic ovary syndrome
DE69529807T2 (de) Neue Parabansäure-Derivate als Aldose-Reduktase Inhibitoren
KR900701797A (ko) α-아드레날린성 수용체 길항질

Legal Events

Date Code Title Description
WITN Application deemed withdrawn, e.g. because no request for examination was filed or no examination fee was paid