WO1984003091A1 - Derives de dihydrobenzofuranne - Google Patents

Derives de dihydrobenzofuranne Download PDF

Info

Publication number
WO1984003091A1
WO1984003091A1 PCT/JP1984/000014 JP8400014W WO8403091A1 WO 1984003091 A1 WO1984003091 A1 WO 1984003091A1 JP 8400014 W JP8400014 W JP 8400014W WO 8403091 A1 WO8403091 A1 WO 8403091A1
Authority
WO
WIPO (PCT)
Prior art keywords
hydrochloride
dihydro
acid
lower alkyl
compound
Prior art date
Application number
PCT/JP1984/000014
Other languages
English (en)
Japanese (ja)
Inventor
Tetsuya Tahara
Toru Nakao
Hiroshi Mikashima
Hiroshi Yasuda
Original Assignee
Yoshitomi Pharmaceutical
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 Yoshitomi Pharmaceutical filed Critical Yoshitomi Pharmaceutical
Publication of WO1984003091A1 publication Critical patent/WO1984003091A1/fr

Links

Classifications

    • 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
    • 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
    • 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
    • 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

Definitions

  • the present invention relates to a novel compound of the general formula
  • R 1 represents hydrogen, lower alkyl, nodogen, hydroxy, lower alkoxy, and R 2 represents hydrogen, lower alkyl
  • a dihydrobenzofuran derivative represented by the formula: a dihydrobenzofuran derivative represented by the formula: .
  • lower alkyl refers to methyl, ethyl, brovir, isopropyl, butyl, etc.
  • lower alkoxy refers to methoxy, ethoxy, propoxy, isopropoxy, butoxy, etc.
  • nitrogen refers to chlorine and bromine. , Fluorine, etc.
  • the compound of the present invention represented by the general formula (I) can be produced, for example, by the following method. -Method 1
  • X represents a halogen (chlorine, bromine, etc.), and RR 2 is as defined above.
  • This reaction is carried out by heating in a suitable solvent in the presence of a large excess of imidazole or a suitable diacid.
  • Acidic agents include sodium carbonate, sodium carbonate, sodium bicarbonate, triethylamine, viridin, and the like.
  • Solvents include tosolen, N, N-dimethyl These include Chinore Hozolem Amide, Ethanore, and Isopropanol. For example, when a large excess of imidazole is used in a mixed solvent of!, N-dimethylformamide with toluene and heated to reflux, the reaction proceeds favorably.
  • R 2 in the general formula (I) is a lower alkyl.
  • the compound of the general formula (I) thus obtained may be a hydrochloride, a sulfate, It can be a pharmaceutically acceptable acid addition salt such as hydrobromide, quinate, maleate, fumarate and the like.
  • the compounds of the present invention is useful because of their pharmacological action, such as selective filtrated Nbokisan A 2 synthase inhibitory action, platelet aggregation inhibitory action, myocardial infarction, angina pectoris, as a preventive or therapeutic agent for thrombosis
  • the compound of the present invention When used as a medicament, the compound of the present invention may be used alone or in the form of a mixture with an appropriate pharmaceutically acceptable carrier, excipient, diluent, or the like, in the form of powder, granules, tablets, capsules, injections, or the like. It can be administered orally or parenterally.
  • the dosage may vary depending on the disease to be treated and the condition, but is preferably in the range of 0.1 to 100 tag / day per 1 kg of human body weight.
  • Extract with Rinse with water dry with a carbon dioxide realm and concentrate under reduced pressure.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Medicinal Chemistry (AREA)
  • Cardiology (AREA)
  • Heart & Thoracic Surgery (AREA)
  • Diabetes (AREA)
  • Hematology (AREA)
  • Urology & Nephrology (AREA)
  • Vascular Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

Dérivés de dihydrobenzofuranne représentés par la formule générale (I), (où R1 représente un hydrogène, un alkyle inférieur, un halogène, un hydroxy ou un alcoxy inférieur, et R2 représente un hydrogène ou un alkyle inférieur) et leurs sels d'addition d'acide. Ces composés sont utiles en tant qu'agents pour la prophylaxie et le traitement de l'infarctus du myocarde, de l'angine de poitrine, des thromboses, etc.
PCT/JP1984/000014 1983-02-01 1984-01-20 Derives de dihydrobenzofuranne WO1984003091A1 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
JP58015870A JPS59225183A (ja) 1983-02-01 1983-02-01 ジヒドロベンゾフラン誘導体

Publications (1)

Publication Number Publication Date
WO1984003091A1 true WO1984003091A1 (fr) 1984-08-16

Family

ID=11900827

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1984/000014 WO1984003091A1 (fr) 1983-02-01 1984-01-20 Derives de dihydrobenzofuranne

Country Status (2)

Country Link
JP (1) JPS59225183A (fr)
WO (1) WO1984003091A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54145665A (en) * 1978-02-01 1979-11-14 Wellcome Found Imidazole derivative
JPS57131787A (en) * 1980-12-12 1982-08-14 Schering Plough Corp Novel benzo(b)thiphenes, benzo(b)furans, thiochromans and chromans, manufacture and bactericidal composition containing same

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS54145665A (en) * 1978-02-01 1979-11-14 Wellcome Found Imidazole derivative
JPS57131787A (en) * 1980-12-12 1982-08-14 Schering Plough Corp Novel benzo(b)thiphenes, benzo(b)furans, thiochromans and chromans, manufacture and bactericidal composition containing same

Also Published As

Publication number Publication date
JPS59225183A (ja) 1984-12-18
JPH0261952B2 (fr) 1990-12-21

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