GB495783A - New therapeutically valuable quinoline derivatives - Google Patents
New therapeutically valuable quinoline derivativesInfo
- Publication number
- GB495783A GB495783A GB1390537A GB1390537A GB495783A GB 495783 A GB495783 A GB 495783A GB 1390537 A GB1390537 A GB 1390537A GB 1390537 A GB1390537 A GB 1390537A GB 495783 A GB495783 A GB 495783A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methyl
- iodide
- prepared
- hydroxyethylamino
- sulphate
- 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
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/38—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
New trypanocidal agents of the general formula <FORM:0495783/IV/1> where Ar = phenylene or substituted phenylene, Alk = alkyl, Ac = an acid residue, and where one X = acylamino, and the other = <FORM:0495783/IV/2> Z1 being hydroxyalkyl and Z2 being hydrogen or alkyl, are prepared either by interacting a p - acylaminobenzaldehyde with an alkyl-6-(N - hydroxyalkylamino) - quinaldinium salt or with an alkyl-6-(N-alkyl-N-hydroxyalkylamino)-quinaldinium salt or by interacting a 6-acylaminoquinaldinium salt with a p-(N - hydroxyalkylamino) - benzaldehyde or with a p-(N-alkyl-N-hydroxyalkylamino)benzaldehyde. Reaction is conveniently effected by refluxing the substances dissolved in a suitable solvent, e.g. methanol or ethanol, with the addition of a small proportion of a secondary amine (e.g. piperidine or diethylamine). Examples describe the preparation of (1) Methyl 2-(41-acetylaminostyryl)-6-(N-b -hydroxyethylamino) - quinolinium chloride by treating with lime the corresponding sulphate obtained from methyl 6-(N-b -hydroxyethylamino)-quinaldinium methyl sulphate (prepared by condensing 6-aminoquinaldine with ethylene chlorhydrin and treating the product with dimethyl sulphate) and p-acetylaminobenzaldehyde; (2) methyl 2-(41-acetylaminostyryl) - 6 - (N - g - hydroxypropylamino)-quinolinium chloride by refluxing with silver chloride the corresponding iodide, obtained by treating 6-(N-g -hydroxypropylamino)-quinaldinium iodide (prepared from 6-aminoquinaldine and trimethylene chlorhydrin, followed by methyl iodide) with p-acetylaminobenzaldehyde; (3) similar methods are employed to those of examples (1) and (2) with acetylaminobenzaldehydes which are substituted in the nucleus by methyl, methoxy or chlorine; (4) Methyl-2-(41-N-b -hydroxy-ethylaminostyryl) - 6 - acetylamino - quinolinium methyl sulphate is prepared from p-(N-b -hydroxyethylamino) - benzaldehyde and methyl - 6 - acetylamino - quinaldinium methyl sulphate. Other aldehydes which may be employed are: 3-methyl-4-N-b -hydroxyethylaminobenzaldehyde; p - (N - g -hydroxypropylamino) - benzaldehyde; 3-methyl - 4 - N - g - hydroxypropylaminobenzaldehyde; p-(N - methyl - N - b - hydroxyethylamino) - benzaldehyde; p-(N-ethyl-N-b -hydroxyethylamino) - benzaldehyde. These aldehydes may be prepared by suitable adaptation of the process described in German Specification 105,105; (5) methyl 2-(41-acetylaminostyryl) - 6 - (N - methyl - N - b - hydroxyethylamino) - quinolinium chloride from the corresponding iodide obtained by treating 6 - (N - methyl - N - b - hydroxyethylamino)-quinaldinium iodide (prepared by condensing 6-aminoquinaldine with ethylenechlorhydrin and treating the product with methyl iodide and sodium carbonate) with p-acetylaminobenzaldehyde; (6) methyl 2-(41-N - ethyl-N-b - hydroxyethylaminostyryl) - 6 - n - caproylamino-quinolinium methyl sulphate is prepared from 6 - n - caproylaminoquinaldinium methyl sulphate and p-(N-ethyl-N-b -hydroxyethylamino) - benzaldehyde. Similarly methyl 2 - (31 - methyl - 41 - N - b - hydroxyethylaminostyryl) - 6 - n - caproylaminoquinolinium methyl sulphate may be prepared; (7) methyl-2 - (41 - acetylaminostyryl) - 6 - (N - ethyl - N-g - hydroxypropylaminoquinolinium chloride from the corresponding iodide obtained by treating methyl - 6 - (N - ethyl - N - g - hydroxypropylamino) quinaldinium iodide (prepared by treating methyl - 6 - (N-g -hydroxypropylaminoquinaldinium iodide with ethyl iodide and sodium carbonate), with p-acetylaminobenzaldehyde. Similarly methyl 2-(41-acetylaminostyryl) - 6 - (N - methyl - N - g - hydroxypropylamino) - quinolinium iodide and chloride, and methyl 2-(41-propionylaminostyryl)-6-(N-g -hydroxypropylamino) -quinolinium iodide and chloride may be made.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1390537A GB495783A (en) | 1937-05-18 | 1937-05-18 | New therapeutically valuable quinoline derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB1390537A GB495783A (en) | 1937-05-18 | 1937-05-18 | New therapeutically valuable quinoline derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB495783A true GB495783A (en) | 1938-11-18 |
Family
ID=10031506
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB1390537A Expired GB495783A (en) | 1937-05-18 | 1937-05-18 | New therapeutically valuable quinoline derivatives |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB495783A (en) |
-
1937
- 1937-05-18 GB GB1390537A patent/GB495783A/en not_active Expired
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