GB599967A - Improvements in soluble sulfanilamide derivatives and process of preparing same - Google Patents
Improvements in soluble sulfanilamide derivatives and process of preparing sameInfo
- Publication number
- GB599967A GB599967A GB24809/45A GB2480945A GB599967A GB 599967 A GB599967 A GB 599967A GB 24809/45 A GB24809/45 A GB 24809/45A GB 2480945 A GB2480945 A GB 2480945A GB 599967 A GB599967 A GB 599967A
- Authority
- GB
- United Kingdom
- Prior art keywords
- sulphanilamido
- pyrimidine
- pyridine
- chloride
- reacted
- 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
Landscapes
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Sulphanilamide derivatives of the general formula <FORM:0599967/IV/1> wherein R stands for hydrogen or alkyl, R1 is a quaternary nitrogen radical and R11 is a heterocyclic ring, are prepared by reacting with a tertiary amine a sulphanilamide derivative substituted in position N4 by an aliphatic a -halogeno-acyl radical and in position N1 by said heterocyclic ring. The product may be isolated as the free base, the intramolecular anhydride of the base, or in the form of a salt of the base. The a -halogeno-acyl compound is prepared by reacting a sulphanilamide derivative having a free amino group in position N4 and substituted in position H1 by said heterocyclic ring, with an anhydride or halogenide of an aliphatic a -halogenic acid. In examples: (1) the chloride of 2-N4-[N-pyridinium-acetyl]-sulphanilamido-thiazole is made by adding pyridine to a refluxing suspension of 2 - N4 - chloroacetyl - sulphanilamido - thiazole in dioxane; (2) the chloride of 2-N4-[N-pyridiniumacetyl]-sulphanilamido-pyridine is prepared by refluxing pyridine, 2-N4-chloroacetyl-sulphanilamido-pyridine and alcohol; (3) the chloride of 2 - N4 - [N - pyridinium - acetyl] - sulphanilamido - pyrimidine is prepared by adding pyridine to a refluxing solution of 2 - N4 - chloroacetyl - sulphanilamido-pyrimidine in dioxane; (4) 2-sulphanilamido - thiazole hydrochloride and a - bromopropionyl bromide are reacted to give 2 - N4 - a - bromopropionyl - sulphanilamido - thiazole, which is then reacted with pyridine in the presence of alcohol to yield the bromide of 2 - N4 - [N - a - pyridinium - propionyl] - sulphanilanido-thiazole; (5) 2-N4-a -bromopropionyl-sulphanilamido-pyrimidine is made (a) by adding a solution of a -bromopropionyl bromide in benzene to sulphanilamido-pyrimidine hydrochloride in water, or (b) by adding a -bromopropionyl bromide to sulphanilamido-pyrimidine, acetone and pyridine; the 2-N4-a -bromopropionyl-sulphanilamido - pyrimidine is then dissolved in alcohol and reacted with pyridine to give the bromide of 2-N4-[N-a -pyridiniumpropionyl]-sulphanilamido-pyrimidine; (6) the chloride of 2-N4-a -chloropropionyl-sulphanilamido-pyrimidine is prepared from 2-sulphanilamido-pyrimidine hydrochloride and a -chloropropionyl chloride, which is then reacted with pyridine to give the chloride of 2-N4-[N-a -pyridinium-propionyl]-sulphanilamido-pyrimidine; (7) 2-N4-chloroacetyl-sulphanilamidothiazole is reacted with trimethylamine in water to give the chloride of 2 - N4 - [trimethyl - ammonium - acetyl] - sulphanilamido - thiazole; (8) 2-N4-chloroacetyl-sulphanilamido-pyridine is reacted with trimethylamine in water to give the chloride of 2-N4-[trimethylammoniumacetyl]-sulphanilamido-pyridine; (9) 2-N4 - chloroacetyl - sulphanilamido - pyrimidine is reacted with aqueous trimethylamine to give the chloride of 2-N4-[trimethylammoniumacetyl]-sulphanilamido-pyrimidine; and (10) 2-N4-a -bromoprionyl-sulphanilamido-pyrimidine is reacted with aqueous trimethylamine to give the bromide of 2 - N4 - [a - trimethyl - ammonium-propionyl]-sulphanilamido-pyrimidine.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US599967XA | 1944-08-16 | 1944-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB599967A true GB599967A (en) | 1948-03-25 |
Family
ID=22026661
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB24809/45A Expired GB599967A (en) | 1944-08-16 | 1945-09-25 | Improvements in soluble sulfanilamide derivatives and process of preparing same |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB599967A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2947743A (en) * | 1959-05-12 | 1960-08-02 | Hoffmann La Roche | N4-aminoacetyl-, n4-lower alkylaminoacetyl- and n4-di-lower alkylamino-acetyl-6-sulfanilamido-2, 4-dimethoxypyrimidines |
-
1945
- 1945-09-25 GB GB24809/45A patent/GB599967A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2947743A (en) * | 1959-05-12 | 1960-08-02 | Hoffmann La Roche | N4-aminoacetyl-, n4-lower alkylaminoacetyl- and n4-di-lower alkylamino-acetyl-6-sulfanilamido-2, 4-dimethoxypyrimidines |
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