CH239698A - Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. - Google Patents
Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide.Info
- Publication number
- CH239698A CH239698A CH239698DA CH239698A CH 239698 A CH239698 A CH 239698A CH 239698D A CH239698D A CH 239698DA CH 239698 A CH239698 A CH 239698A
- Authority
- CH
- Switzerland
- Prior art keywords
- amino
- salt
- ethyl
- calcium
- pyrimidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 150000003839 salts Chemical class 0.000 title claims description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical class NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 title claims description 3
- -1 amido nitrogen Chemical compound 0.000 claims description 6
- 159000000007 calcium salts Chemical class 0.000 claims description 6
- 230000007935 neutral effect Effects 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 229910052791 calcium Inorganic materials 0.000 claims description 3
- 239000011575 calcium Substances 0.000 claims description 3
- 208000035473 Communicable disease Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 2
- 229930195733 hydrocarbon Natural products 0.000 claims 1
- 150000002430 hydrocarbons Chemical class 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000000243 solution Substances 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- COSZGCBTURPTLV-UHFFFAOYSA-N 4-amino-N-(4-ethylpyrimidin-2-yl)benzenesulfonamide Chemical compound CCC1=CC=NC(NS(=O)(=O)C=2C=CC(N)=CC=2)=N1 COSZGCBTURPTLV-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- XKQVDEFVQCERKW-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(S(=O)(=O)NC2=NC=CC(=N2)CC)C=C1 Chemical compound C(C)(=O)NC1=CC=C(S(=O)(=O)NC2=NC=CC(=N2)CC)C=C1 XKQVDEFVQCERKW-UHFFFAOYSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 206010047700 Vomiting Diseases 0.000 description 1
- 206010000059 abdominal discomfort Diseases 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940043430 calcium compound Drugs 0.000 description 1
- 150000001674 calcium compounds Chemical class 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 231100000869 headache Toxicity 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000008673 vomiting Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen 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
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/69—Benzenesulfonamido-pyrimidines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines Salzes eines Abkömmlings des p-Amino-benzolsulfonamids. Gegenstand der Erfindung ist ein Ver fahren zur Darstellung des neutralen, Kalzium salzes des 2-(p-Amino-benzol-sulfonylamino)- 4-äthyl-pyrimidins. Es wurde gefunden, dass das Kalziumsalz dieses neuen Sulfonamides neben hervorragenden antibakteriellen Eigen schaften eine grössere Verträglichkeit besitzt als die bekannten freien Sulfonamide und insbesondere weniger Magenbeschwerden, Kopfschmerz und Erbrechen erzeugt als diese.
Dem in unsern schweizerischen Paten ten Nr.<B>213815</B> und 213816 beschriebenen 2 - (p-Amino - Benzol - sulf onylamino)-pyridin- calcium gegenüber hat das neue Kalziumsalz den Vorzug grösserer Wasserlöslichkeit. Da zudem seine wässerige Lösung praktisch neutral reagiert, eignet es sich gut zu Injek tionen, was bei dem 2-(p-Amino-benzol- sulfonylamino) - pyridin - caleium nicht der Fall ist.
Die neue Kalziumverbindung soll zur Bekämpfung infektiöser Erkrankungen, speziell der durch Strepto-, Gono- und Pneumokokken verursachten, Verwendung finden.
Das Verfahren zur Darstellung des neuen Sulfonamidsalzes ist dadurch gekennzeich net, dass man ein 2-(p-Acylamino-benzol- sulfonylamino)-4-äthyl-pyrimidin mit einer Lösung von Kalziumhydroxyd behandelt, wobei durch Ersatz des am Amidostickstoff sitzenden Wasserstoffatoms durch Kalzium und Verseifung der Acy lgruppe das neutrale Kalziumsalz des 2-(p-Aminobenzol-sulfonyl- amino)-4-äthyl-pyrimidins entsteht.
Zur Darstellung der neuen Verbindung verfährt man beispielsweise folgendermassen: 7,5 g 2-(p-Acetylamino-benzol-sulfonyl- amino)-4-äthyl-pyrimidin werden mit einer Lösung von 7,5 g Kalziumhydrogyd in 280 cm' Wasser 6 Stunden auf 130 C er hitzt. Die noch heisse Lösung wird über Ent- färbungskohle filtriert. Aus dem Filtrat scheidet sich beim Erkalten das neutrale Kalziumsalz des 2-(p-Amino-benzol-sulfonyl- amino )-4-ä.thy 1-py rimidins in beinahe quanti tativer Ausbeute aus.
Es bildet farblose Prismen, die sich, ohne zu schmelzen, ober halb \?50 C zu zersetzen beginnen. Es ist gut löslich in heissem Wasser und heissem Pvridin, schwer löslich in Alkohol, unlöslich in Kohlemvasserstoffen.
Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. The invention relates to a process for the preparation of the neutral, calcium salt of 2- (p-amino-benzene-sulfonylamino) -4-ethyl-pyrimidine. It has been found that the calcium salt of this new sulfonamide, in addition to excellent antibacterial properties, is more tolerable than the known free sulfonamides and, in particular, causes fewer stomach upsets, headaches and vomiting than these.
The new calcium salt has the advantage of greater water solubility compared to the 2 - (p-amino - benzene - sulfonylamino) pyridine calcium described in our Swiss patent nos. <B> 213815 </B> and 213816. Since its aqueous solution also reacts practically neutrally, it is well suited for injections, which is not the case with 2- (p-amino-benzenesulfonylamino) -pyridine-caleium.
The new calcium compound is said to be used to combat infectious diseases, especially those caused by streptococci, gonococci and pneumococci.
The process for preparing the new sulfonamide salt is characterized in that a 2- (p-acylamino-benzenesulfonylamino) -4-ethyl-pyrimidine is treated with a solution of calcium hydroxide, with the hydrogen atom on the amido nitrogen being replaced by calcium and Saponification of the acyl group produces the neutral calcium salt of 2- (p-aminobenzene-sulfonyl-amino) -4-ethyl-pyrimidine.
The procedure for preparing the new compound is as follows: 7.5 g of 2- (p-acetylamino-benzene-sulfonyl-amino) -4-ethyl-pyrimidine are treated with a solution of 7.5 g of calcium hydrogen in 280 cm 'of water for 6 hours it heats up to 130 C. The still hot solution is filtered through decolorizing charcoal. When the filtrate cools, the neutral calcium salt of 2- (p-amino-benzene-sulfonyl-amino) -4-Ä.thy 1-pyrimidine separates out in an almost quantitative yield.
It forms colorless prisms, which begin to decompose above 50 ° C without melting. It is readily soluble in hot water and hot pvridine, sparingly soluble in alcohol, insoluble in carbon dioxide.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH213816T | 1943-06-23 | ||
| CH239698T | 1943-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH239698A true CH239698A (en) | 1945-10-31 |
Family
ID=25725504
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH239698D CH239698A (en) | 1943-06-23 | 1943-06-23 | Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH239698A (en) |
-
1943
- 1943-06-23 CH CH239698D patent/CH239698A/en unknown
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