GB974348A - Basic 7-chloroquinoline-1-oxide derivatives and methods for their production - Google Patents

Basic 7-chloroquinoline-1-oxide derivatives and methods for their production

Info

Publication number
GB974348A
GB974348A GB295161A GB295161A GB974348A GB 974348 A GB974348 A GB 974348A GB 295161 A GB295161 A GB 295161A GB 295161 A GB295161 A GB 295161A GB 974348 A GB974348 A GB 974348A
Authority
GB
United Kingdom
Prior art keywords
oxide
dichloroquinoline
radical
chloroquinoline
arsanilates
Prior art date
Legal status (The legal status 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 status listed.)
Expired
Application number
GB295161A
Inventor
Edward Faith Elslager
Frank Hulit Tendick
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Parke Davis and Co LLC
Original Assignee
Parke Davis and Co LLC
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 Parke Davis and Co LLC filed Critical Parke Davis and Co LLC
Priority to GB295161A priority Critical patent/GB974348A/en
Publication of GB974348A publication Critical patent/GB974348A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07DHETEROCYCLIC COMPOUNDS
    • C07D215/00Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/58Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
    • C07D215/60N-oxides

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)

Abstract

The invention comprises compounds of the general formula <FORM:0974348/C1/1> (wherein Y represents a hydrogen, chlorine or bromine atom or a methyl, allyl or methoxy group, and R1 and R2 may be the same or different and each represent a hydrogen atom, an aliphatic (including cycloaliphatic) hydrocarbon, hydroxyhydrocarbon or alkoxyhydrocarbon radical of not more than 12 carbon atoms or a tetrahydrofurfuryl radical (but are not both hydrogen atoms) or they are combined as an alkylene, oxa-alkylene or aza-alkylene chain, optionally bearing hydrocarbon or hydroxy substituents, so as to form with the nitrogen atom a heterocyclic radical of fewer than 10 carbon atoms (including a 1-decahydroquinolyl radical)), and their non-toxic acid addition salts (including benzyl- and phenoxymethyl-penicillinates, fumagillinates, N-acetyl-4-hydroxy-m-arsanilates, N-glycollyl-p-arsanilates, N, N1-ethylene-bis-p-arsanilates and p-ureidobenzene-arsonates), and the preparation thereof by reacting a 4-halo-7-chloroquinoline-1-oxide (preferably 4, 7-dichloroquinoline-1-oxide) with an aminophenol of the formula <FORM:0974348/C1/2> or by reacting a compound of the formula <FORM:0974348/C1/3> with formaldehyde and an amine R1NHR2, and in either case, if desired, converting a resulting acid addition salt into the free base or a resulting free base into a non-toxic acid addition salt. The products have antiparasitic (e.g. anti-malarial, anthelmintic and amebicidal), anti-bacterial, antiviral and anti-inflammatory properties. 4, 7-Dichloroquinoline-1-oxide is prepared by treating 4, 7-dichloroquinoline with perbenzoic acid in chloroform. 4-(p-Hydroxyphenylamino)-7-chloroquinoline-1-oxide is prepared by condensing 4, 7-dichloroquinoline-1-oxide with p-aminophenol. Aminophenols of the second general formula above are prepared, in the form of aqueous solutions of their dihydrochlorides, by hydrolyzing with hydrochloric acid the corresponding acetamidophenols obtained by condensing p-acetamidophenol with formaldehyde and amines R1NHR2.
GB295161A 1961-01-25 1961-01-25 Basic 7-chloroquinoline-1-oxide derivatives and methods for their production Expired GB974348A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB295161A GB974348A (en) 1961-01-25 1961-01-25 Basic 7-chloroquinoline-1-oxide derivatives and methods for their production

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB295161A GB974348A (en) 1961-01-25 1961-01-25 Basic 7-chloroquinoline-1-oxide derivatives and methods for their production

Publications (1)

Publication Number Publication Date
GB974348A true GB974348A (en) 1964-11-04

Family

ID=9749126

Family Applications (1)

Application Number Title Priority Date Filing Date
GB295161A Expired GB974348A (en) 1961-01-25 1961-01-25 Basic 7-chloroquinoline-1-oxide derivatives and methods for their production

Country Status (1)

Country Link
GB (1) GB974348A (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0027679A2 (en) * 1979-10-18 1981-04-29 Warner-Lambert Company Substituted-5-((7-chloro-4-quinolinyl)amino)-3-(amino-methyl)-(1,1'-biphenyl)-2-ol compounds; processes for their production; and pharmaceutical compositions containing the compounds
WO1984000489A1 (en) * 1982-07-26 1984-02-16 American Hospital Supply Corp Heteroaryl substituted aminomethyl benzene derivatives, compositions and use
WO2001092232A1 (en) * 2000-05-27 2001-12-06 Ufc Ltd. 4-aminoquinolines as antiinfective agents
WO2002072554A1 (en) * 2001-03-14 2002-09-19 The University Of Liverpool Anti-malarial compounds
EP1603884A2 (en) * 2003-02-28 2005-12-14 Encysive Pharmaceuticals Inc. Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-ii receptor antagonists.

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0027679A2 (en) * 1979-10-18 1981-04-29 Warner-Lambert Company Substituted-5-((7-chloro-4-quinolinyl)amino)-3-(amino-methyl)-(1,1'-biphenyl)-2-ol compounds; processes for their production; and pharmaceutical compositions containing the compounds
EP0027679A3 (en) * 1979-10-18 1981-07-15 Warner-Lambert Company Substituted-5-((7-chloro-4-quinolinyl)amino)-3-(amino-methyl)-(1,1'-biphenyl)-2-ol compounds; processes for their production; pharmaceutical compositions containing the compounds; intermediate compounds for use in said processes; and production of the intermediates
WO1984000489A1 (en) * 1982-07-26 1984-02-16 American Hospital Supply Corp Heteroaryl substituted aminomethyl benzene derivatives, compositions and use
WO2001092232A1 (en) * 2000-05-27 2001-12-06 Ufc Ltd. 4-aminoquinolines as antiinfective agents
WO2002072554A1 (en) * 2001-03-14 2002-09-19 The University Of Liverpool Anti-malarial compounds
US7132431B2 (en) 2001-03-14 2006-11-07 The University Of Liverpool Anti-malarial compounds
EP1603884A2 (en) * 2003-02-28 2005-12-14 Encysive Pharmaceuticals Inc. Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-ii receptor antagonists.
EP1603884A4 (en) * 2003-02-28 2008-05-28 Encysive Pharmaceuticals Inc Pyridine, pyrimidine, quinoline, quinazoline, and naphthalene urotensin-ii receptor antagonists.

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