CH237324A - 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
- CH237324A CH237324A CH237324DA CH237324A CH 237324 A CH237324 A CH 237324A CH 237324D A CH237324D A CH 237324DA CH 237324 A CH237324 A CH 237324A
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- benzene
- amino
- salt
- pyrimidine
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title claims description 4
- 239000011780 sodium chloride Substances 0.000 title claims description 4
- 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 p - acetylamino-benzene-sulfonylamino- Chemical class 0.000 claims description 7
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N 289-95-2 Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229920001098 polystyrene-block-poly(ethylene/propylene) Polymers 0.000 claims 45
- 230000002458 infectious Effects 0.000 claims 1
- 150000003230 pyrimidines Chemical class 0.000 claims 1
- NJIZUWGMNCUKGU-UHFFFAOYSA-N N(4)-acetylsulfadiazine Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=NC=CC=N1 NJIZUWGMNCUKGU-UHFFFAOYSA-N 0.000 description 3
- UXVMQQNJUSDDNG-UHFFFAOYSA-L cacl2 Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 201000009910 diseases by infectious agent Diseases 0.000 description 1
- 230000002708 enhancing Effects 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000001225 therapeutic 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
Description
Verfahren zur Darstellung eines Salzes eines Abkömmlings des p-Amino- benzolsulfonamids. Das in neuester Zeit bekannt gewordene 2- (p-Acetylamino-benzol-sulfonylamino-)py- rimidin hat sich als geeignet erwiesen zur Bekämpfung infektiöser, insbesondere durch Kokken hervorgerufener Krankheiten.
Es wurde nun gefunden, dass das durch Ersatz des Wasserstoffatoms seiner Sulfon- amidgruppe durch Kalzium erhältliche Kal- ziumsalz des 2-(p-Acetylamino-benzol-sulfo- nylamino-)pyrimidins gegenüber der entspre chenden Wasserstoffverbindung die oben er wähnten therapeutischen Eigenschaften in verstärktem Masse aufweist und ausserdem eine bessere Verträglichkeit besitzt. Die neue Verbindung soll daher zur Bekämpfung in fektiöser Erkrankungen, speziell der durch Strepto-, Gono- und Pneumokokken verursach ten, verwendet werden.
Das erfindungsgemässe Verhhren zur Darstellung der neuen Verbindung ist da durch gekennzeichnet, dass man 2-(p-Acetyl- amino-benzol-sulfonylamino-)pyrimidin und eine zum Austausch des Wasserstoffes der Sulfonamidgruppe gegen Kalziiun befähigte Verbindung, z.
B. Kalziumhydrogyd, lös liches galziumsalz, wie Kalziumchlorid, auf einander einwirken lässt, wobei sich das Di- [2 - (p - Acetylamino-benzol - sulfonylamino)- pyrimidin]-ealcium bildet.
<I>Ausführungsbeispiel:</I> 20 g 2-(p-Acetylamino-benzol-sulfonyl- amino-)pyrimidin werden in stark konzen triertem, wässerigem Ammoniak gelöst. Zu der warmen Lösung fügt man tropfenweise eine konzentrierte, heisse, wässerige Lösung von zirka 100 g Kalziumchlorid. Man lässt über Nacht stehen, nutscht das auskristalli sierte Di- [2-(p-Acetylamino-benzol-sulfonyl- amino-)pyrimidin]-calcium ab und wäscht es mit wenig kaltem Wasser. Die Ausbeute be trägt 16 g.
Die neue, farblose, kristalline Verbin dung zersetzt sich oberhalb 250 C ohne zu schmelzen, ist sowohl in warmem als auch in kaltem Wasser ziemlich löslich, ebenfalls in Pyridin, wenig löslich in Alkohol, schwer löslich in Azeton, Äther und Benzol.
Process for the preparation of a salt of a derivative of p-Amino-benzenesulfonamide. The recently known 2- (p-acetylamino-benzene-sulfonylamino) pyrimidine has proven to be suitable for combating infectious diseases, in particular those caused by cocci.
It has now been found that the calcium salt of 2- (p-acetylamino-benzene-sulfonylamino-) pyrimidine, which can be obtained by replacing the hydrogen atom of its sulfonamide group with calcium, enhances the above-mentioned therapeutic properties compared with the corresponding hydrogen compound Has mass and also has better compatibility. The new compound should therefore be used to combat fectious diseases, especially those caused by streptococci, gonococci and pneumococci.
The process according to the invention for the preparation of the new compound is characterized in that 2- (p-acetylamino-benzene-sulfonylamino) pyrimidine and a compound capable of exchanging the hydrogen of the sulfonamide group for calcium, eg.
B. calcium hydrogen, soluble galcium salt, such as calcium chloride, can act on each other, forming the di- [2 - (p - acetylamino-benzene - sulfonylamino) - pyrimidine] -ealcium.
<I> Exemplary embodiment: </I> 20 g of 2- (p-acetylamino-benzene-sulfonyl-amino) pyrimidine are dissolved in highly concentrated, aqueous ammonia. A concentrated, hot, aqueous solution of about 100 g of calcium chloride is added dropwise to the warm solution. It is left to stand overnight, the di- [2- (p-acetylamino-benzene-sulfonyl-amino) pyrimidine] calcium which has crystallized out is suction filtered and washed with a little cold water. The yield be 16 g.
The new, colorless, crystalline compound decomposes above 250 C without melting, is fairly soluble in both warm and cold water, also in pyridine, slightly soluble in alcohol, sparingly soluble in acetone, ether and benzene.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH237324T | 1941-10-28 | ||
| CH213815T | 1943-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH237324A true CH237324A (en) | 1945-04-15 |
Family
ID=25725499
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH237324D CH237324A (en) | 1941-10-28 | 1941-10-28 | Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH237324A (en) |
-
1941
- 1941-10-28 CH CH237324D patent/CH237324A/en unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CH237324A (en) | Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. | |
| CH221517A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH221515A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| DE876999C (en) | Process for the production of pellets of 4-aminobenzenesulfonamide | |
| CH213815A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH237323A (en) | Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. | |
| CH237326A (en) | Process for the preparation of a salt of a sulfonamide. | |
| CH221516A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH237325A (en) | Process for the preparation of a salt of a sulfonamide. | |
| DE875660C (en) | Process for the production of ª † .ª † -diphenyl-allylamines or their hydrogenation products | |
| AT151657B (en) | Process for the preparation of formaldehyde sodium sulfoxylates from arsenobenzene compounds. | |
| DE606400C (en) | Process for the preparation of complex compounds of secondary or tertiary oxyalkylamines | |
| AT145519B (en) | Process for the preparation of complex compounds of secondary or tertiary oxyalkylamines. | |
| AT146635B (en) | Process for the preparation of compounds of dihydrocodeine, which are readily soluble in water, with alkylated barbituric acids. | |
| CH221518A (en) | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. | |
| CH237322A (en) | Process for the preparation of a salt of a sulfonamide. | |
| CH239699A (en) | Process for the preparation of a salt of a sulfonamide. | |
| CH237327A (en) | Process for the preparation of a salt of a derivative of p-amino-benzenesulfonamide. | |
| CH204380A (en) | Process for preparing an aminobenzenesulfonic acid amide compound. | |
| CH237575A (en) | Process for the preparation of 2-amino-thiazole-5-sulfonanilide. | |
| CH220404A (en) | Process for the preparation of a new derivative of a heterocyclic compound. | |
| CH237574A (en) | Process for the preparation of 2-acetylamino-thiazole-5-sulfonanilide. | |
| CH237573A (en) | Process for the preparation of 2-amino-thiazole-5-sulfonamide. | |
| CH213150A (en) | Process for the preparation of a derivative of 2-amino-6-methylpyridine. | |
| CH169578A (en) | Process for the preparation of the salt of 2,3-dimethoxy-6-nitro-9- (Y-diethylamino-B-oxy-propylamino) -acridine with p-glycolylaminobenzolaric acid. |