GB630913A - Improvements in or relating to substituted quinoline antimalarials and a process of making them - Google Patents
Improvements in or relating to substituted quinoline antimalarials and a process of making themInfo
- Publication number
- GB630913A GB630913A GB8379/47A GB837947A GB630913A GB 630913 A GB630913 A GB 630913A GB 8379/47 A GB8379/47 A GB 8379/47A GB 837947 A GB837947 A GB 837947A GB 630913 A GB630913 A GB 630913A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethoxy
- methyl
- prepared
- carbon atoms
- ethyl
- 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
- C07D215/40—Nitrogen atoms attached in position 8
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Quinoline Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
5 : 6-Dimethoxy-8-substituted quinolines of the general formula <FORM:0630913/IV (b)/1> wherein R represents a polymethylene chain containing from 4 to 5 carbon atoms and is substituted with a methyl or ethyl radical on one of the terminal carbon atoms, and R1 represents an alkyl radical containing from 1 to 6 carbon atoms, are prepared by condensing 5 : 6 - dimethoxy - 8 - aminoquinoline and the hydrohalide, e.g. the hydrobromide, of an alkylaminoalkylhalide of the general formula <FORM:0630913/IV (b)/2> wherein R and R1 have the above significance and Ha represents chlorine or bromine. The condensation may be carried out in aqueous solution buffered to a pH of 4.8 by the addition of disodium phosphate citric acid buffer, and the temperature may then be maintained within a few degrees of 45 DEG C. for a period of 12 to 14 hours, raised progressively to between 95 DEG and 100 DEG C. and maintained at that temperature for a period of 5 to 6 hours. The group R1 may represent methyl, ethyl, propyl, isopropyl and the several butyl, pentyl and hexyl radicals. In examples, 5 : 6-dimethoxy-8-(11-methyl - 41 - isopropylaminobutylamino)-, 5 : 6-dimethoxy - 8 - (11 - methyl - 51 - isopropylaminopentylamino)-, 5 : 6-dimethoxy-8-(41-ethyl-41-ethylaminobutylamino)-, 5 : 6-dimethoxy-8-(11-methyl - 41 - ethylaminobutylamino)-, 5 : 6 - dimethoxy-8-(11-methyl-41-n-propylaminobutylamino) -, 5 : 6-dimethoxy-8-(11-methyl-41-isobutylaminobutylamino)-, and 5 : 6-dimethoxy-8-(11-methyl-41-tert.-butylaminobutylamino) - quinolines are prepared. The substituted quinolines may be converted into their salts, e.g. the oxalates, hydrohalides, phosphates or citrates. Amines.-1 - Methyl - 4 - n - propylaminobutylbromide hydrobromide is prepared by reacting thionyl bromide and 1-n-propylaminopentonol-4, which may be prepared by reacting 1-chloropentonol-4 with n-propylamine. The Specification as open to inspection under Sect. 91 states that 5 : 6-dimethoxy-8-aminoquinoline may be prepared in accordance with U.S.A. Specification 1,879,538. This subject-matter does not appear in the Specification as accepted.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US630913XA | 1946-04-08 | 1946-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB630913A true GB630913A (en) | 1949-10-24 |
Family
ID=22046864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8379/47A Expired GB630913A (en) | 1946-04-08 | 1947-03-27 | Improvements in or relating to substituted quinoline antimalarials and a process of making them |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB630913A (en) |
-
1947
- 1947-03-27 GB GB8379/47A patent/GB630913A/en not_active Expired
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