KR910000688A - Paf 길항제로서 2,5-디아릴 테트라하이드로푸란 및 이의 동족체 - Google Patents

Paf 길항제로서 2,5-디아릴 테트라하이드로푸란 및 이의 동족체 Download PDF

Info

Publication number
KR910000688A
KR910000688A KR1019900008393A KR900008393A KR910000688A KR 910000688 A KR910000688 A KR 910000688A KR 1019900008393 A KR1019900008393 A KR 1019900008393A KR 900008393 A KR900008393 A KR 900008393A KR 910000688 A KR910000688 A KR 910000688A
Authority
KR
South Korea
Prior art keywords
propoxy
phenyl
tetrahydroxyfuran
trans
trimethoxyphenyl
Prior art date
Application number
KR1019900008393A
Other languages
English (en)
Inventor
비프투 테스페이
앤. 기로트라 니린다
앰. 폰피폼 미트리
Original Assignee
제임스 에프, 너튼
머크 앤드 캄파니, 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, 너튼, 머크 앤드 캄파니, 인코포레이티드 filed Critical 제임스 에프, 너튼
Publication of KR910000688A publication Critical patent/KR910000688A/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
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D307/12—Radicals substituted by oxygen atoms
    • 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
    • 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
    • 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
    • A61P37/02—Immunomodulators
    • A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
    • 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
    • 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
    • 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

Landscapes

  • Health & Medical Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Chemical & Material Sciences (AREA)
  • Public Health (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Immunology (AREA)
  • Pulmonology (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Pain & Pain Management (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Transplantation (AREA)
  • Rheumatology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
  • Furan Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Formation Of Insulating Films (AREA)

Abstract

내용 없음

Description

PAF 길항제로서 2,5-디아릴 테트라하이드로푸란 및 이의 동족체
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (19)

  1. 일반식(Ⅰ)의 화합물 또는 이의 약제학적으로 허용되는 염;
    상기식에서, R4는 S(O)nR2이고 n은 0,1 또는 2이며, R2는 (a)C2-6알킬, (b)치환된 C1-6알킬 (여기서, 치환체는 하이드록시, 아미노, N-C1-4알킬아미노 및 N,N-디-N-C1-4알킬아미노로 구성된 그룹으로부터 선택된다). 및 (c)C1-6알킬카보닐-C1-6알킬로 구성된 그룹으로부터 선택되고, Y는 (a)C1-12알킬, (b)C1-6하이드록시알킬, (c)C1-6알킬카보닐-C1-6알킬, 및 (d)비치환되거나, 일-또는 이치환된 아미노 C1-6알킬 (여기서 치환체는 C1-6알킬이다)로 구성된 그룹에서 선택되고, R6는 (a)치환된 C1-6알킬 [여기서, 치환체는 하이드록시, 아미노, N-C1-4알킬아미노, N,N-디-C1-4알킬아미노, 및 -O-R10(여기서 R10은 (1) -PO2(oH)--M+(M+는 약제학적으로 허용가능한 일가 양이온이다). (2) -SO3-M+또는, (3) -C(O) (CH2)2-CC2O-M+이다)로 구성된 그룹에서 선택된다), (b)C1-6알킬카보닐-C1-6알킬, 또는 (c)C1-6카복시알킬로 구성된 그룹에서 선택된다.
  2. 제1항에 있어서, 테트라하이드로푸란의 2 및 5위치의 치환체가 서로에 대해 트랜스 위치에 있으며, n이 2이고, R2는 (a) 치환된 C1-6알킬(여기서, 치환체는 하이드록시, 아미노, N-C1-4알킬아미노 및 N,N-디-N-C1-4알킬아미노로 이루어진 그룹으로부터 선택된다), 및 (b)C1-6알킬카보닐-C1-6알킬로 구성딘 그룹에서 선택되며, Y는 (a)C1-6알킬 또는 (b)C1-4알킬키보닐-C1-4알킬인 화합물.
  3. 제2항에 있어서, R6가 (a)치환된 C1-6알킬 [여기서, 치환체는 하이드록시, 아미노, N-C1-4알킬아미노 및 N,N-디-C1-4알킬 아미노, 및 -O-R10(여기서 R10은 (1) -PO2(OH)--M+(M+는 약제학적으로 허용가능한 양이온이다), (2) -SO3 -M+, 또는 (3) -C(O)(CH2)2-CO2-M+이다)로 구성된 그룹에서 선택된다]. (b) C1-6알킬카보닐-C1-6알킬로 구성된 그룹에서 선택되고, Y가 n-프로필 또는 2-옥소프로필인 화합물.
  4. 제3항에 있어서, (a) 트랜스-2-[3-(2-옥스프로필설포닐)-4-n-프로폭시-5-(3-(N,N-디메틸아미노)-n-프로폭시)페닐]-5-(3,4,5-트리메톡시-페닐)테트라하이드록푸란, (b) 트랜스-2-[3-(2-옥스프로필설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시-페닐)테트라하이드록푸란, (c) 트랜스-[3-(2-옥스프로필설포닐)-4-n-프로폭시-5-(3-포스폰옥시프로폭시)페닐]5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (d) 트랜스-2-[3-(2-옥스프로필설포닐)-4-n-프로폭시-5-(2-옥소프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (e) 트랜스-2-[3-(2-하이드록시-n-프로필설포닐)-4-n-프로폭시-5(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (f) 트랜스-2-[3-(2-하이드록시-n-프로필설포닐)-4-n-프로폭시-5(2-옥소프로폭시-페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (g) 트랜스-2-[3-(2-아미노-n-프로필-설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)-페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (h) 트랜스-2-[3-(2-N-메틸아미노-n-프로필-설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (i) 트랜스-2-[3-(2-N,N-디메틸아미노-프로필설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (j) 트랜스-2-[3-(2-N-에틸아미노-n-프로필설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (k) 트랜스-2-[3-(2-N-메틸아미노에틸-설포닐)-4,5-디-n-프로폭시페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (l) 트랜스-2-[3-(2-N,N-디메틸아미노에틸-설포닐)-4,5-디-n-프로폭시페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (m) 트랜스-2-[3-(2-아미노에틸설포닐)-4,5-디-n-프로폭시페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (n) 트랜스-2-[3-(2-N-에틸아미노에틸설포닐)-4,5-디-n-프로폭시페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (o) 트랜스-2-[3-(2-N-프로필아미노에틸-설포닐)-4,5-디-n-프로폭시페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (p) 트랜스-2-[3-(2-N,N-디메틸아미노에틸-설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (q) 트랜스-2-[3-(2-N,N-디메틸아미노에틸-설포닐)-4-n-프로폭시-5-(2-옥소-프로폭시-페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (r) 트랜스-2-[3-(2-하이드록시설포닐)-4-n-프로폭시-5-(2-옥소-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (s) 트랜스-2-[3-(2-N,N-디메틸아미노에틸-설포닐)-4-n-프로폭시-5-(2-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, 화합물, 또는 이의 (2S, 5S)배위의 입체화학적 이성체.
  5. 제4항에 있어서, (a) 트랜스-2-[3-(2-옥스프로필설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시-페닐)테트라하이드록푸란, (b) 트랜스-2-[3-(2-옥스프로필-설포닐)-4-n-프로폭시-5-(3-프로폰옥시)프로목시 페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, 또는 (c) 트랜스-2-[3-(2-하이드록시)-n-프로필-설포닐-4-n 프로폭시-5-(3-하이드록시-n-프로폭시)페닐]5-(3,4,5-트리메톡시페닐)테트라하이드록푸란인 화합물.
  6. 제5항에 있어서, (a) (2S, 5S)-2-[3-(2-옥소프로필설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (b) (2S, 5S)-2-[3-((2S)-2-하이드록시)-n-프로필설포닐-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란, (c) (2S, 5S)-2-[3-(2-하이드록시-n-프로필-설포닐)-4-n-프로폭시-5-(3-하이드록시-n-프로폭시)페닐]5-(3,4,5-트리메톡시페닐)테트라하이드록푸란 또는, (d) (-)(2S, 5S)-2-[3-{(2S)-2-하이드록시프로필-설포닐}-4-n-프로폭시-5-{3-(포스포노옥시)-프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란인 화합물.
  7. 제5항에 있어서, (-)(2S, 5S)-2-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-(3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐)테트라하이드록푸란인 화합물.
  8. 비독성적 치료적 유효량의 제1항에 따른 화합물 및 약학적으로 허용되는 담체를 함유하는, PAF의 효과를 길항시키기 위한 약제학적 조성물.
  9. 비독성 치료적 유효량의 제5항에 따른 화합물 및 약학적으로 허용되는 담체를 함유하는, PAF의 효과를 길항시키기 위한 약제학적 조성물.
  10. 제9항에 있어서, 활성 성분이 (-)트랜스-(2S, 5S)-2-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-(3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란인 조성물.
  11. 비독성적 치료적 유효량의 제1항에 따른 화합물을 PAF 효과의 길항작용이 요구되는 환자에게 투여함을 특징으로 하여, 상기 환자의 PAF의 효과를 길항시키는 방법.
  12. 비독성적 치료적 유효량의 제5항에 따른 화합물을 PAF 효과의 길항작용이 요구되는 환자에게 투여함을 특징으로 하여, 상기 환자의 PAF의 효과를 길항시키는 방법.
  13. 제12항에 있어서, 활성 성분이 (-)트랜스-(2S, 5S)-2-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-(3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란인 방법.
  14. (2S, 5S) 배위의 일반식(Ⅰ) 화합물 또는 이의 약제학적으로 허용되는 염.
    상기식에서, R4는 SO2CH2COOH3이고, Y는 -CH2CH2CH3이며, R6는 -(CH2)3-O-PO2(OH)7M+및 치환된 -(CH2)3-O-PO2(OH)-(여기에서, 치환체는
    M은 약학적으로 허용되는 일가 양이온이며, M1는 약학적으로 허용되는 아미노산 양이온이고, M2는 약학적으로 허용되는 2가 양이온이다)로부터 선택된다.
  15. 제14항에 있어서, R4가 SO2CH2CO, CH3(2S, 5S)이고, Y는 -CH2CH2CH3이며, R6는 (a) -(CH2)3-C-PO2(OH)7M+(여기서, M는 나트륨, 칼륨, 암모늄, 리튬, 리신 또는 오르니틴이다) 또는, (b)
    (상기식에서, M은 K이고 M1은 오르니틴이거나, M은 Na이고 M1은 오르니틴이거나, M은 Li이고 M1은 오르니틴이거나, M은 K이고, M1은 리신이거나, M은 Na이고 M1은 리신이거나 또는 M은 Li이고, M1은 리신이다)인 화합물.
  16. 제15항에 있어서, (a) (-)-트랜스-(2S, 5S)-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-[3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란 일칼륨 염, (b) (-)-트랜스-(2S, 5S)-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-[3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란 모노리튬 염, (c) (-)-트랜스-(2S, 5S)-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-[3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란 일나트륨 염, (d) (-)-트랜스-(2S, 5S)-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-[3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란 라이신 염 또는, (e) (-)-트랜스-(2S, 5S)-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-[3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란 칼륨 오르니틴 염인 화합물.
  17. 제16항에 있어서, (-)-트랜스-(2S, 5S)-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-[3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란 일칼륨 염인 화합물.
  18. (-)-트랜스-(2S, 5S)-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-[3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시-페닐) 테트라하이드록푸란 일 칼륨 염인 비독성적 치료적 유효량의 제17항의 화합물을 함유하는 PAF 효과를 길항시키기위한 약학적 조성물.
  19. (-)-트랜스-(2S, 5S)-[3-(2-옥소프로필-설포닐)-4-n-프로폭시-5-[3-(포스포노옥시)프로폭시)페닐]-5-(3,4,5-트리메톡시페닐) 테트라하이드록푸란 일칼륨 염인 비독성적 치료적 유효량의 제17항의 화합물을 PAF 효과를 길항시키는 것이 필요한 환자에게 투여함을 특징으로 하여, PAF 효과를 길항하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019900008393A 1989-06-08 1990-06-08 Paf 길항제로서 2,5-디아릴 테트라하이드로푸란 및 이의 동족체 KR910000688A (ko)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US36292089A 1989-06-08 1989-06-08
US362920 1989-06-08
US07/505,712 US4977146A (en) 1989-06-08 1990-04-11 2,5-diaryl tetrahydrofurans and analogs thereof as PAF antagonists
US505712 1990-04-11

Publications (1)

Publication Number Publication Date
KR910000688A true KR910000688A (ko) 1991-01-30

Family

ID=27001844

Family Applications (1)

Application Number Title Priority Date Filing Date
KR1019900008393A KR910000688A (ko) 1989-06-08 1990-06-08 Paf 길항제로서 2,5-디아릴 테트라하이드로푸란 및 이의 동족체

Country Status (14)

Country Link
US (1) US4977146A (ko)
EP (1) EP0402151B1 (ko)
JP (1) JPH07100701B2 (ko)
KR (1) KR910000688A (ko)
AT (1) ATE133947T1 (ko)
AU (1) AU636615B2 (ko)
CA (1) CA2018482A1 (ko)
DE (1) DE69025230D1 (ko)
FI (1) FI902846A0 (ko)
IL (1) IL94585A0 (ko)
NO (1) NO902513L (ko)
NZ (1) NZ233903A (ko)
PT (1) PT94302A (ko)
ZA (1) ZA904391B (ko)

Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5114961A (en) * 1989-06-08 1992-05-19 Merck & Co., Inc. 2,5-diaryl tetrahydrofurans and analogs thereof as PAF antagonists
US5171864A (en) * 1991-08-30 1992-12-15 Allergan, Inc. Di-(5-hydroxy-2(5H)-2-oxo-4-furyl)methyl-alpha,omega alkane-dioates and N,N-bis-(5-hydroxy-2(5H)-2-oxo-4-furyl)methyl-alpha,omega-dialkanoic acid amides as anti-inflammatory agents
US5169963A (en) * 1991-08-30 1992-12-08 Allergan, Inc. Di-(5-hydroxy-2(5H)2-oxo-4-furyl)alkylmethyl-alpha,omega alkanedioates and N,N-bis-(5-hydroxy-2(5H)2-oxo-4-furyl)alkylmethyl-alpha,omega-dialkanoic acid amides as anti-inflammatory agents
US5530141A (en) * 1992-03-04 1996-06-25 Center For Innovative Technology 2,4-diaryl-1,3-dithiolanes; 2,4-diaryl-1,3-dioxolanes; 2,4-diaryl-1,3-oxathiolanes; and 2,5-diaryl-1,3-oxathiolanes for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
US5639782A (en) * 1992-03-04 1997-06-17 Center For Innovative Technology Neolignan derivatives as platelet activating factor receptor antagonists and 5-lipoxygenase inhibitors
US5463083A (en) * 1992-07-13 1995-10-31 Cytomed, Inc. Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5358938A (en) * 1992-07-13 1994-10-25 Cytomed, Inc. Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
US5648486A (en) * 1992-07-13 1997-07-15 Cytomed, Inc. Compounds and methods for the treatment of inflammatory and immune disorders
US5434151A (en) * 1992-08-24 1995-07-18 Cytomed, Inc. Compounds and methods for the treatment of disorders mediated by platelet activating factor or products of 5-lipoxygenase
CA2140034A1 (en) 1992-07-13 1994-01-20 Xiong Cai 2,5-diaryl tetrahydro-thiophenes, -furans and analogs for the treatment of inflammatory and immune disorders
US5792776A (en) * 1994-06-27 1998-08-11 Cytomed, Inc., Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5703093A (en) * 1995-05-31 1997-12-30 Cytomed, Inc. Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
CA2194064C (en) * 1994-06-27 2009-03-17 Xiong Cai Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
US5750565A (en) * 1995-05-25 1998-05-12 Cytomed, Inc. Compounds and methods for the treatment of cardiovascular, inflammatory and immune disorders
EP0875247B1 (en) * 1997-04-18 2003-05-28 Nederlandse Organisatie Voor Toegepast-Natuurwetenschappelijk Onderzoek Tno Method for controlling the plasma level of lipoproteins
US6444664B1 (en) 1997-04-18 2002-09-03 Nederlandse Organisatie Voor Toegepast - Natuurweten Schappelijk Onderzoek (Tno) Method for controlling the plasma level of lipoproteins to treat alzheimeris disease
US6372922B1 (en) * 2001-03-27 2002-04-16 Council Of Scientific And Industrial Research Process for the production of (−) 3,4-divanillyl tetrahydrofuran
AR084486A1 (es) 2010-10-01 2013-05-22 Basf Se Compuestos de imina
US8883857B2 (en) 2012-12-07 2014-11-11 Baylor College Of Medicine Small molecule xanthine oxidase inhibitors and methods of use

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3769350A (en) * 1968-12-09 1973-10-30 Hoffmann La Roche Method for making 2,3-dimethyl-1,4-bis(3,4 - hydrocarbonyloxyphenyl) - 1,4-butanedione
US4539332A (en) * 1983-11-14 1985-09-03 Merck & Co., Inc. 2,5-Diaryl tetrahydrofurans and analogs thereof as PAF-antagonists
US4757084A (en) * 1984-02-29 1988-07-12 Merck & Co., Inc. 2,5-diaryl tetrahydrothiophenes and analogs thereof as PAF-antagonists
IT8434016V0 (it) * 1984-03-12 1984-03-12 Zanussi A Spa Industrie Perfezionamenti ai dispositivi ammortizzatori ad attrito per lavabiancheria.
US4595693A (en) * 1984-06-04 1986-06-17 Merck & Co., Inc. Method of use of 2,5-diaryl tetrahydrofurans and analogs thereof as PAF-antagonists
NZ215866A (en) * 1985-04-22 1989-11-28 Merck & Co Inc 2,5-di(aryl/heterocyclyl) tetrahydro-furans and pharmaceutical compositions
GB2197650A (en) * 1986-11-21 1988-05-25 Merck & Co Inc Process for preparing 2,5-diphenyl tetrahydrofurans and analogs thereof
NZ227287A (en) * 1987-12-21 1992-01-29 Merck & Co Inc 2,5-diaryl tetrahydrofurans and medicaments

Also Published As

Publication number Publication date
AU5692690A (en) 1990-12-13
AU636615B2 (en) 1993-05-06
IL94585A0 (en) 1991-04-15
US4977146A (en) 1990-12-11
NO902513L (no) 1990-12-10
EP0402151A1 (en) 1990-12-12
NO902513D0 (no) 1990-06-06
FI902846A0 (fi) 1990-06-07
ZA904391B (en) 1991-03-27
JPH03101670A (ja) 1991-04-26
PT94302A (pt) 1991-02-08
EP0402151B1 (en) 1996-02-07
ATE133947T1 (de) 1996-02-15
JPH07100701B2 (ja) 1995-11-01
DE69025230D1 (de) 1996-03-21
NZ233903A (en) 1992-09-25
CA2018482A1 (en) 1990-12-08

Similar Documents

Publication Publication Date Title
KR910000688A (ko) Paf 길항제로서 2,5-디아릴 테트라하이드로푸란 및 이의 동족체
SE8002218L (sv) Nya morfolinoforeningar
KR890011592A (ko) 기관내 허혈병의 치료용 조성물
SE7708592L (sv) Forfarande for framstellning av fosfonsyraderivat
HUT68721A (en) Benzofuran and benzizoxazole derivatives, pharmaceutical composition containing said compounds as active agent and process for preparing them
ES483289A1 (es) Un procedimiento para la preparacion de 1,2,3,5, tetrahidro-himidazotienopirimidin-2-onas.
KR900018113A (ko) 티에노-트리아졸로-디아제핀 유도체, 그의 제조 방법 및 그를 함유하는 치료 조성물
ES2039851T3 (es) Procedimiento para la obtencion de 3-(metano-sulfoniloxi) tiolano opticamente activo y sus analogos.
IL88518A (en) 3-(phosphoryl methoxyethoxy) -purine derivatives, their preparation and pharmaceutical compositions containing them
ES8305730A1 (es) Un procedimiento para la preparacion de un derivado del imidazol.
HU190579B (en) Plant growth regulating compositions comprising etherified hydroxy-alkyl-phosphonic acid-derivatives as active substance
SE7907689L (sv) Nya hydroxamsyraforeningar, sett for deras framstellning samt anvendning av dessa foreningar som lekemedel
BR9911624B1 (pt) processos para sintetizar um fungicida e para controlar doença em uma planta, compostos heterocìclicos substituìdos de cinco membros e composição fungicida contendo os mesmos.
ES547604A0 (es) Un procedimiento para preparar derivados de 2-piridin-tiol
SE8405719L (sv) Mellanprodukter for framstellning av nya 2-substituerade och 2,6-disubstituerade penem-foreningar
KR900007811A (ko) 1-아미노알킬-3옥시치환된-4-아릴-1,3,4,5-테트라하이드로-2h-1.3-벤조디아제핀-2-은, 이의 제조방법 및 이의 약제로서의 용도
FR2418792A1 (fr) Derives de 3-azabicyclo(3.1.0)hexane, procede pour leur preparation, compositions biologiquement actives les contenant et procede herbicide les utilisant
US4007171A (en) Intermediates for prostanoic acids
US4337337A (en) 2,5-Inter-o-phenylene-3,4-dinor-5,9α-epoxy-6-iodo-PGF1 compounds
AU6675696A (en) A novel asymmetric synthesis of r and s warfarin and its analogs
US4144251A (en) 5-Unsaturated prostanoic acid derivatives
IL98524A0 (en) Enantiomers of tetrahydrofuran derivatives,their preparation and pharmaceutical compositions containing them
SE8102331L (sv) Nya terpenderivat, sett for deras framstellning och insekticida medel innehallande dem
Abraham et al. Alkyl derivatives of 4, 5-dehydro PGF 1
KR890013024A (ko) 말론산 유도체, 그의 제조방법 및 용도

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