CH213815A - Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. - Google Patents
Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide.Info
- Publication number
- CH213815A CH213815A CH213815DA CH213815A CH 213815 A CH213815 A CH 213815A CH 213815D A CH213815D A CH 213815DA CH 213815 A CH213815 A CH 213815A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridine
- calcium
- salt
- sulfonylamino
- derivative
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- 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 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 15
- -1 p-aminobenzene - sulfonylamino - Chemical class 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- 229910052791 calcium Inorganic materials 0.000 claims description 4
- 239000011575 calcium Substances 0.000 claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 4
- 208000035473 Communicable disease Diseases 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000000565 sulfonamide group Chemical group 0.000 claims description 3
- 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
- 238000002844 melting Methods 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- YXOIKGINCRKOBC-UHFFFAOYSA-N calcium;pyridine Chemical group [Ca].C1=CC=NC=C1 YXOIKGINCRKOBC-UHFFFAOYSA-N 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 159000000007 calcium salts Chemical class 0.000 description 4
- 239000012452 mother liquor Substances 0.000 description 3
- GECHUMIMRBOMGK-UHFFFAOYSA-N sulfapyridine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=CC=CC=N1 GECHUMIMRBOMGK-UHFFFAOYSA-N 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 239000001110 calcium chloride Substances 0.000 description 2
- 229910001628 calcium chloride Inorganic materials 0.000 description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 2
- 239000000920 calcium hydroxide Substances 0.000 description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- QPFYXYFORQJZEC-FOCLMDBBSA-N Phenazopyridine Chemical compound NC1=NC(N)=CC=C1\N=N\C1=CC=CC=C1 QPFYXYFORQJZEC-FOCLMDBBSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 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
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 229940070891 pyridium Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 201000008827 tuberculosis Diseases 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Perfabr en zur Darstellung eines Salzes eines Abkömmlings des p-Aminobenzolsulfonamids. Das in neuester Zeit bekannt gewordene 2-(p-Aminobenzol-sulfonylamino-) pyridin hat sich als geeignet erwiesen zur Bekämpfung infektiöser, insbesondere durch Kokken her vorgerufener Krankheiten.
Es wurde nun gefunden,- dass das durch Er satz des Wasserstoffatoms seiner Sulfonamid gruppe durch Kalzium erhältliche Kalzium- salz des 2-(p-Aminobenzol-sulfonylamino-)py- ridins gegenüber der entsprechenden Wasser stoffverbindung die oben erwähnten therapeu tischen Eigenschaften in verstärktem Masse aufweist, ausserdem eine bessere Verträglich keit besitzt, und, wie aus den klinischen Un tersuchungen hervorgeht, wahrscheinlich auch einen günstigen Einfluss auf die Tuberkulose auszuüben vermag.
Die neue Verbindung soll daher zur Bekämpfung infektiöser Erkran kungen, speziell der durch Strepto-, Gono- und Pneumokokken verursachten, verwendet werden.
Das erfindungsgemässe Verfahren zur Dar stellung der neuen Verbindung ist dadurch gekennzeichnet, dass man 2-(p-Aminobenzol- sulfonylamino-)pyridin und eine zum Aus tausch des Wasserstoffes der Sulfonamidgruppe gegen Kalzium befähigte Verbindung, z. B. Kalziumhydroxyd, lösliches Kalziumsalz, wie Kalziumchlorid, aufeinander einwirken lässt, wobei sich Di-[2-(p-Aminobenzöl-sulfonyl- amino-)pyridin-] calcium bildet.
<I>1. Ausführungsbeispiel:</I> 25 g 2-(p-Aminobenzol-sulfonylamino-)py- ridin und<B>3,7</B> g Kalziumhydroxyd werden in 700 cm3 heissem Wasser gelöst. Die Lösung wird so lange gekocht, bis die anfänglich vorhandene Trübung beinahe verschwunden ist; hierauf wird die noch heisse Lösung mit Tierkohle versetzt und filtriert. Beim Erkalten kristallisiert das Kalziumsalz grösstenteils aus.
Weitere Mengen können durch Einengen der Mutterlauge gewonnen werden.
<I>2.</I> Ausführungsbeispiel: Eine Lösung von 2-(p-Aminobenzol-sulfonyl- amino-)pyridin in wenig verdünnter Salzsäure wird bis zum Aufhören der Kohlendioxydent- wicklung mit Kalziumkarbonat versetzt. Das hierbei ausgefällte Kalziumsalz des 2-(p-Amino- benzol - sulfonylamino - )pyridins wird abge- nutscht und aus heissem Wasser umkristalli siert.
<I>3. Ausführungsbeispiel:</I> 10 g 2-(p-Aminobenzol-sulfoiiylamirio-)-py- ridin werden in 100 cm' 20-prozentigem Ammoniak in der Hitze gelöst. Zu dieser Lö sung wird eine wässerige, konzentrierte Lö sung von Kalziumchlorid im Überschuss zu gegeben. Nach einiger Zeit kristallisiert das Kalziumsatz des 2 - (p -Aminobenzol- sulfonyl- amino-)pyridiiis aus und wird nach dem Er kalten durch Absaugen von der Mutterlauge getrennt. Die Ausbeute beträgt 10 g ; sie kann durch Einengen der Mutterlauge erhöht werden.
Die neue Verbindung bildet sechsseitige Prismen. Sie zersetzt sich beim Erhitzen ohne zu schmelzen, ist leicht löslich in heissem Pyridin, ziemlich gut löslich in kaltem Pyri- din und heissem Wasser, wenig löslich in kal tem Wasser, in Alkohol und Azeton.
Perfabr en for the preparation of a salt of a derivative of the p-aminobenzenesulfonamide. The recently known 2- (p-aminobenzene-sulfonylamino-) pyridine has proven to be suitable for combating infectious diseases, especially those caused by cocci.
It has now been found that the calcium salt of 2- (p-aminobenzene-sulfonylamino) pyridine obtained by replacing the hydrogen atom of its sulfonamide group with calcium increases the above-mentioned therapeutic properties to a greater extent than the corresponding hydrogen compound also has better tolerability and, as the clinical investigations show, is probably also able to exert a beneficial influence on tuberculosis.
The new compound should therefore be used to combat infectious diseases, especially those caused by streptococci, gonococci and pneumococci.
The inventive method for the presentation of the new compound is characterized in that 2- (p-aminobenzene sulfonylamino) pyridine and a compound capable of exchanging the hydrogen of the sulfonamide group for calcium, eg. B. calcium hydroxide, soluble calcium salt, such as calcium chloride, can act on each other, with di- [2- (p-aminobenzol-sulfonyl- amino-) pyridine-] calcium being formed.
<I> 1. Exemplary embodiment: 25 g of 2- (p-aminobenzene-sulfonylamino) pyridine and 3.7 g of calcium hydroxide are dissolved in 700 cm3 of hot water. The solution is boiled until the initial cloudiness has almost disappeared; the still hot solution is then mixed with animal charcoal and filtered. Most of the calcium salt crystallizes out on cooling.
Further quantities can be obtained by concentrating the mother liquor.
<I> 2nd </I> embodiment example: A solution of 2- (p-aminobenzene-sulfonyl-amino-) pyridine in a little dilute hydrochloric acid is mixed with calcium carbonate until the evolution of carbon dioxide ceases. The calcium salt of 2- (p-aminobenzene - sulfonylamino -) pyridine precipitated in the process is filtered off with suction and recrystallized from hot water.
<I> 3. Exemplary embodiment: 10 g of 2- (p-aminobenzene-sulfoiiylamirio-) - pyridine are dissolved in 100 cm 'of 20 percent ammonia in the heat. An aqueous, concentrated solution of calcium chloride in excess is added to this solution. After some time, the calcium residue of the 2- (p -aminobenzenesulfonylamino) pyridium crystallizes out and, after cooling, is separated from the mother liquor by suction. The yield is 10 g; it can be increased by concentrating the mother liquor.
The new connection forms six-sided prisms. It decomposes when heated without melting, is easily soluble in hot pyridine, fairly soluble in cold pyridine and hot water, slightly soluble in cold water, in alcohol and acetone.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH213815T | 1943-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH213815A true CH213815A (en) | 1941-03-15 |
Family
ID=4448415
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH213815D CH213815A (en) | 1943-03-13 | 1939-11-03 | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH213815A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2613170A (en) * | 1944-03-02 | 1952-10-07 | Physiological Chemicals Compan | Calcium sulfanilamide preparations |
-
1939
- 1939-11-03 CH CH213815D patent/CH213815A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2613170A (en) * | 1944-03-02 | 1952-10-07 | Physiological Chemicals Compan | Calcium sulfanilamide preparations |
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