GB703484A - New quinolinium salts - Google Patents
New quinolinium saltsInfo
- Publication number
- GB703484A GB703484A GB61151A GB61151A GB703484A GB 703484 A GB703484 A GB 703484A GB 61151 A GB61151 A GB 61151A GB 61151 A GB61151 A GB 61151A GB 703484 A GB703484 A GB 703484A
- Authority
- GB
- United Kingdom
- Prior art keywords
- bis
- amino
- adipamide
- formula
- mixture
- 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
- C07D215/42—Nitrogen atoms attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The invention comprises as new compounds quaternary salts of the formula <FORM:0703484/IV(b)/1> wherein X is hydrogen or an alkyl radical, Y is an alkyl radical, Alk is an alkyl radical, A is an anionic radical and n is an integer from 3 to 12 inclusive. The compounds, particularly those in which n is 4-8 inclusive, possess trypanocidal properties and may be prepared by reacting at elevated temperature a compound of the formula <FORM:0703484/IV(b)/2> with a quaternary salt-forming agent of the formula Alk-A wherein X, Y, Alk, n and A have the meaning stated above, or by reacting at elevated temperature one molecular proportion of an acid halide of the formula Hal-CO-[CH2]-CO-Hal with two molecular proportions of a 6-aminoquinolinium salt of the formula <FORM:0703484/IV(b)/3> wherein X, Y, Alk, A and n are as above and Hal is halogen. In examples (1) N : N1-bis-(4-amino-2-methylquinolyl-6) adipamide is added to a mixture of methyl p-toluenesulphonate and nitrobenzene and the mixture heated to yield N: N1bis-(4-amino-1: 2-dimethylquinolinium-6-)-adipamide di-p-toluene sulphonate; (2) N : N1-bis-(4-amino-1 : 2-dimethylquinolinium-6-) sebacamide di-p-toluene sulphonate is obtained by heating the corresponding substituted sebacamide with methyl p-toluene sulphonate and nitrobenzene; (3) N : N1 - bis - (4 - methylamino - 1 : 2 - dimethyl - quinolinium-6-) adipamide di - p - toluenesulphonate is obtained in a similar manner and by dissolving the latter in water and boiling the solution with sodium chloride N : N1-bis-(4-methylamino-1 : 2-dimethyl-quinolinium-6-) adipamide dichloride is obtained; (4) N : N1 - bis - (4 - amino - 1 : 2 - dimethyl - quinolinium-6-) adipamide dichloride is obtained by heating a mixture of 4 : 6-diaminoquinaldine methochloride, pyridine, and adipyl chloride; (5) N : N1 - bis - (4 - amino - 1 : 2-dimethylquinolinium-6-) pimelamide is obtained by adding methyl p toluene-sulphonate is a boiling solution of N : N1-bis-(4-amino -6-quinaldyl-) pimelamide in nitrobenzene and boiling the mixture. N : N1 - bis - (4 - methylamino- -2 - methylquinolyl-6-) adipamide may be prepared by heating a mixture of 6-amino-4-methylamino quinaldine and adipyl chloride in glacial acetic acid and converting the dihydrochloride formed into the free base by treatment with water and caustic soda solution.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB61151A GB703484A (en) | 1951-01-09 | 1951-01-09 | New quinolinium salts |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB61151A GB703484A (en) | 1951-01-09 | 1951-01-09 | New quinolinium salts |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB703484A true GB703484A (en) | 1954-02-03 |
Family
ID=9707404
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB61151A Expired GB703484A (en) | 1951-01-09 | 1951-01-09 | New quinolinium salts |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB703484A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3312707A (en) * | 1962-12-20 | 1967-04-04 | Ici Ltd | Sparingly soluble salts of the 6, 6-ureylene-bis-(1-methylquinolinium) cation |
-
1951
- 1951-01-09 GB GB61151A patent/GB703484A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3312707A (en) * | 1962-12-20 | 1967-04-04 | Ici Ltd | Sparingly soluble salts of the 6, 6-ureylene-bis-(1-methylquinolinium) cation |
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