GB974348A - Basic 7-chloroquinoline-1-oxide derivatives and methods for their production - Google Patents
Basic 7-chloroquinoline-1-oxide derivatives and methods for their productionInfo
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/58—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems with hetero atoms directly attached to the ring nitrogen atom
- C07D215/60—N-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.
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)
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. |
-
1961
- 1961-01-25 GB GB295161A patent/GB974348A/en not_active Expired
Cited By (8)
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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