CH247123A - Process for the preparation of a salt of N- (4-amino-benzenesulfone) -N'-benzyl urea. - Google Patents
Process for the preparation of a salt of N- (4-amino-benzenesulfone) -N'-benzyl urea.Info
- Publication number
- CH247123A CH247123A CH247123DA CH247123A CH 247123 A CH247123 A CH 247123A CH 247123D A CH247123D A CH 247123DA CH 247123 A CH247123 A CH 247123A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- benzenesulfone
- salt
- preparation
- benzyl urea
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 8
- 238000000034 method Methods 0.000 title claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 4
- 239000000155 melt Substances 0.000 claims description 2
- 150000003388 sodium compounds Chemical class 0.000 claims description 2
- RJNJWHFSKNJCTB-UHFFFAOYSA-N benzylurea Chemical compound NC(=O)NCC1=CC=CC=C1 RJNJWHFSKNJCTB-UHFFFAOYSA-N 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- -1 4-aminobenzene sulfone Chemical class 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 206010028851 Necrosis Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/50—Compounds containing any of the groups, X being a hetero atom, Y being any atom
- C07C311/52—Y being a hetero atom
- C07C311/54—Y being a hetero atom either X or Y, but not both, being nitrogen atoms, e.g. N-sulfonylurea
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Verfahren zur Herstellung eines Salzes des N-(4-Ämino-benzolsulfon)-N'-benzyl-harnstoffes. Lösungen von Salzen der 4-Amino-benzol- sulfonamide werden, sofern sie nicht stark alkalisch reagieren, vielfach für Injektionen verwendet. Für diesen Zweck ist es jedoch von Wichtigkeit, dass die Lösungen möglichst neutral reagieren, da sonst die Gefahr der Nekrosebildung besteht.
Es wurde nun ge funden, dass die Salze des N-(4-Aminobenzol- sulfon)-N'-benzylharnstoffes viel weniger alkalisch reagieren als die vergleichbaren Salze bekannter p-Aminobenzolsulfonamide;
beispielsweise zeigt das Natriumsalz des N- (4-Aminobenzolsulfon) -N'-benzylharnstoffes in 5%iger wässriger Lösung ein p$ von<B>8,5</B> 2, während die Natriumsalze des 2-(p-Amino- benzolsulfamido)-pyridins, des p-Aminoben-:
zolsuHamino-2-thiazols und des 2-Sulfanil- amido-pyrimidins pH-Werte von 11,2, 10,0 bezw. 9,6-9,7 (je in 2 %iger Lösung) auf weisen.
Als Basen kommen für die Herstellung der Salze des N-(4-Aminobenzolsulfon)-N'- benzylharnstGffes Alkalien in Frage, z. B. Natronlauge, Alkalicarbonate und -bicarbo- nate, Magnesiumhydrogyd, Erdalkalihy- drogyde oder auch organische Basen wie z. B. Diäthylamin, Morpholin, Aminoäthanol, Ä.thylendiamin usw.
Gegenstand vorliegenden Patentes ist ein Verfahren zur Herstellung eines Salzes des N - (4.- Amino-benzolsulfon) - N'- benzylharn.- stoffes. Das Verfahren ist dadurch gekenn- zeichnet, dass man -1 Mol einer Verbindung der Formel
EMI0001.0056
mit 1 Mol einer Natriumverbindung der For mel Na-Y, worin X und Y bei der Reaktion sich abspaltende Reste bedeuten,.
umsetzt. Die erhaltene neue Verbindung, das Natrium salz des N-(4-Amino-benzolsulfon)-N'-ben- zylharnstoffes, kristallisiert in feinen Pris men und schmilzt bei 248 . Sie soll therapeu tische Verwendung finden.
Beispiel: 101 Teile N-(4-Amino-benzolsulfon)-N'- benzylharnstoff werden in 333 Volumteilen wässriger, reiner n-Natronlauge gelöst, fil triert und im Vakuum auf etwa 200 Teile eingedampft. Die konzentrierte warme Lö sung wird sofort mit 2000 Teilen Alkohol versetzt. Nach einigem Stehen kristallisiert das Natriumsalz in feinen Prismen aus, die bei 248 schmelzen.
Process for the preparation of a salt of N- (4-aminobenzenesulfone) -N'-benzylurea. Solutions of salts of the 4-amino-benzenesulfonamides are often used for injections, provided they do not have a strongly alkaline reaction. For this purpose, however, it is important that the solutions react as neutrally as possible, otherwise there is a risk of necrosis.
It has now been found that the salts of N- (4-aminobenzenesulfone) -N'-benzylurea have a much less alkaline reaction than the comparable salts of known p-aminobenzenesulfonamides;
For example, the sodium salt of N- (4-aminobenzene sulfone) -N'-benzylurea in 5% aqueous solution has a p $ of <B> 8.5 </B> 2, while the sodium salts of 2- (p-amino- benzenesulfamido) pyridine, des p-aminoben-:
zolsuHamino-2-thiazole and des 2-sulfanilamido-pyrimidine pH values of 11.2, 10.0, respectively. 9.6-9.7 (each in a 2% solution).
Bases that can be used for the preparation of the salts of N- (4-aminobenzene sulfone) -N'-benzyluric acid are alkalis, e.g. B. caustic soda, alkali carbonates and bicarbonates, magnesium hydrogen, alkaline earth metal or organic bases such. B. diethylamine, morpholine, aminoethanol, ethylene diamine etc.
The present patent relates to a process for the preparation of a salt of N - (4.-Amino-benzenesulfone) - N'-benzylur.- substance. The process is characterized in that -1 mol of a compound of the formula
EMI0001.0056
with 1 mol of a sodium compound of the formula Na-Y, in which X and Y are radicals which are split off during the reaction.
implements. The new compound obtained, the sodium salt of N- (4-amino-benzenesulfone) -N'-benzylurea, crystallizes in fine prisms and melts at 248. It should find therapeutic use.
Example: 101 parts of N- (4-amino-benzenesulfone) -N'-benzylurea are dissolved in 333 parts by volume of pure aqueous n-sodium hydroxide solution, filtered and evaporated to about 200 parts in vacuo. The concentrated warm solution is immediately mixed with 2000 parts of alcohol. After standing for a while, the sodium salt crystallizes out in fine prisms which melt at 248.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH247123T | 1944-12-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH247123A true CH247123A (en) | 1947-02-15 |
Family
ID=4466008
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH247123D CH247123A (en) | 1944-12-28 | 1944-12-28 | Process for the preparation of a salt of N- (4-amino-benzenesulfone) -N'-benzyl urea. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH247123A (en) |
-
1944
- 1944-12-28 CH CH247123D patent/CH247123A/en unknown
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