CH314845A - Process for the preparation of guanylhydrazono-pyruvaldehyde-m-guanyl-phenylhydrazone-carbonate - Google Patents
Process for the preparation of guanylhydrazono-pyruvaldehyde-m-guanyl-phenylhydrazone-carbonateInfo
- Publication number
- CH314845A CH314845A CH314845DA CH314845A CH 314845 A CH314845 A CH 314845A CH 314845D A CH314845D A CH 314845DA CH 314845 A CH314845 A CH 314845A
- Authority
- CH
- Switzerland
- Prior art keywords
- guanyl
- carbonate
- phenylhydrazone
- pyruvaldehyde
- preparation
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 5
- 239000000843 powder Substances 0.000 claims description 5
- AIJULSRZWUXGPQ-UHFFFAOYSA-N pyruvic aldehyde Natural products CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 3
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 125000005638 hydrazono group Chemical group 0.000 claims 1
- 208000015181 infectious disease Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940120731 pyruvaldehyde Drugs 0.000 claims 1
- 229910017604 nitric acid Inorganic materials 0.000 description 4
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229910002651 NO3 Inorganic materials 0.000 description 2
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 2
- 206010037075 Protozoal infections Diseases 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- BAKYASSDAXQKKY-UHFFFAOYSA-N 4-Hydroxy-3-methylbenzaldehyde Chemical compound CC1=CC(C=O)=CC=C1O BAKYASSDAXQKKY-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- FKFMMMVFFYPIEE-UHFFFAOYSA-N [(3-aminophenyl)-azaniumylidenemethyl]azanium;dichloride Chemical compound Cl.Cl.NC(=N)C1=CC=CC(N)=C1 FKFMMMVFFYPIEE-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung von Guanylhydrazono-brenztraubenaldehyd-m-guanyl- phenylhydrazon-carbonat
Gegenstand der vorliegenden Erfindung ist ein Verfahren xur Herstellung von Gua nylhydrazono-brenztraubenaldehyd-m-guahyl- phenylhydrazon-carbonat der Formel
EMI1.1
das dadurch gekennzeichnet ist, dass man Brenztraubenaldehyd-m-guanyl-phenylhydra- zon mit Aminoguanidin kondensiert und das Kondensationsprodukt in das Carbonat überf hrt.
Die so erhaltene Verbindung ist ein grau- gelbes, in kaltem Wasser schwerlösliches Pul- ver, das sich durch Wirksamkeit gegen proto zoische Infektionen auszeichnet.
Das Carbonat lϯt sich bequem in beliebige, leicht wasserlösliche Salze überführen, die sich ebenfalls durch Wirksamkeit gegen protozoische Infektionen auszeichnen, wobei ihre Anwendung zweckmässig in Form der wasserlöslichen Salze erfolgt.
Beispiel
27 g Brenztraubenaldehyd-m-guanyl-phe- nylhydrazon-nitrat werden in 200 cm3 Wasser nach Ansäuern mit etwas verdünnter Salpetersäure mit einer Losung von 14 g Amino- guanidinnitrat in 65 em3 Wasser versetzt. Die Mischung wird 1 Stunde unter Rühren im Wasserbad erwärmt, nach dem Abkühlen wird überschüssige verdünnte Salpetersäure hinzu- gef gt, das Dinitrat obiger Verbindung abgesaugt und mit N-Salpetersäure und Aceton gewaschen. Es bildet ein braunrotes Pulver, das in heissem Wasser leicht, in kaltem mässig löslieh ist und nach dem Umkristallisieren aus Wasser bei 262 unter Zersetzung schmilzt.
Das Dinitrat wird mit Sodalosung in das Carbonat übergeführt, das ein graugelbes, in kaltem Wasser schwerlösliches Pulver darstellt.
Das als Ausgangsmaterial verwendete Brenztraubenaldehyd-m-guanyl-phenylhydrazon wird analog der p-Verbindung hergestellt (vgl. Hauptpatent) unter Verwendung von m-Amino-benzamidin-dihydrochlorid (Berichte der Deutschen Chem. Ges. 28, Seite 486) und d-Lire. Versetzen der Losung seines salzsau- ren Salzes mit verdünnter Salpetersäure als Nitrat gefällt. Dieses bildet ein hellrotbraunes Pulver ; aus Wasser umkristallisiert : F. = 209 bis 210 (Zersetzung).
Process for the preparation of guanylhydrazono-pyruvaldehyde-m-guanyl-phenylhydrazone-carbonate
The present invention relates to a process for the preparation of gua nylhydrazono-pyruvette aldehyde-m-guahylphenylhydrazone carbonate of the formula
EMI1.1
which is characterized in that pyruvaldehyde-m-guanyl-phenylhydrazone is condensed with aminoguanidine and the condensation product is converted into the carbonate.
The compound obtained in this way is a gray-yellow powder which is sparingly soluble in cold water and which is distinguished by its effectiveness against protozoal infections.
The carbonate can be conveniently converted into any readily water-soluble salts, which are also distinguished by their effectiveness against protozoal infections, their use being expediently in the form of the water-soluble salts.
example
27 g of pyruvic aldehyde m-guanyl-phenylhydrazone nitrate are mixed in 200 cm3 of water after acidification with somewhat dilute nitric acid with a solution of 14 g of aminoguanidine nitrate in 65 cm3 of water. The mixture is heated for 1 hour with stirring in a water bath, after cooling, excess dilute nitric acid is added, the dinitrate of the above compound is suctioned off and washed with N-nitric acid and acetone. It forms a brownish-red powder which is easily soluble in hot water and moderately soluble in cold water and, after recrystallization from water, melts at 262 with decomposition.
The dinitrate is converted into carbonate with soda solution, which is a gray-yellow powder that is sparingly soluble in cold water.
The pyruvic aldehyde m-guanyl-phenylhydrazone used as the starting material is prepared analogously to the p-compound (cf. main patent) using m-amino-benzamidine dihydrochloride (reports from Deutsche Chem. Ges. 28, page 486) and d-Lire . Adding dilute nitric acid to the solution of its hydrochloric acid precipitated as nitrate. This forms a light red-brown powder; Recrystallized from water: F. = 209 to 210 (decomposition).
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE314845X | 1950-07-24 | ||
| DE314848X | 1950-07-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH314845A true CH314845A (en) | 1956-06-30 |
Family
ID=32991741
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH314845D CH314845A (en) | 1950-07-24 | 1951-07-16 | Process for the preparation of guanylhydrazono-pyruvaldehyde-m-guanyl-phenylhydrazone-carbonate |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH314845A (en) |
-
1951
- 1951-07-16 CH CH314845D patent/CH314845A/en unknown
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