CH213816A - 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
- CH213816A CH213816A CH213816DA CH213816A CH 213816 A CH213816 A CH 213816A CH 213816D A CH213816D A CH 213816DA CH 213816 A CH213816 A CH 213816A
- 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
- 239000011780 sodium chloride Substances 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 22
- -1 amido nitrogen Chemical compound 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 5
- 239000011575 calcium Substances 0.000 claims description 5
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 239000000920 calcium hydroxide Substances 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- 201000009910 diseases by infectious agent Diseases 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 0.000 claims description 3
- 125000002252 acyl group Chemical group 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- 238000007127 saponification reaction Methods 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N ethanone Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 231100000730 tolerability Toxicity 0.000 description 1
- 201000008827 tuberculosis Diseases 0.000 description 1
- 238000010626 work up procedure Methods 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
Description
Verfahren 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 Ersatz des Wasserstoffatoms seiner Sulfon- amidgruppe durch Kalzium erhältliche Kal- ziumsalz des 2-(p.Aminobenzol-sulfonylamino-)- pyridins 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 Tln- 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 -Acylamino- benzol- sulfonylamino -)pyridin mit einer Lö sung von Kalziumhydroxyd behandelt, wobei durch Verseifung der Acylgruppe und Ersatz des am Amidostickstoff sitzenden Wasserstoff atoms durchKalzium das Di-[2-(p-Aminobenzol- sulfonylamino-)
pyridin-] calcium entsteht. <I>1.</I> Ausführungsbeispiel,: 5 g 2-(p-Acetylaminobenzol-sulfonylamino-)- pyridin werden mit einer Lösung von 5 g Kalziumhydroxyd üi 250 cm3 Wasser 35 Stun den verkocht.
Das beim Abkühlen auskristal lisierende Di - [2 - (p - Aminobenzol- sulfonyl- amino-)pyridin-]calcium wird gesammelt; die Ausbeute beträgt 5 g und kann durch Ein engen der Mutterlauge erhöht werden. Die Reinigung erfolgt durch Umkristallisieren aus heissem Wasser.
<I>2.</I> Ausführungsbeispiel: 5 g 2-(p-Acetylaminobenzol-sulfonylamino-)- pyridin werden mit einer Lösung von 5 g Katziumhydroxyd in 250 cm' Wasser 10 Stun den auf 130 C erhitzt. Die Hydrolyse des Acetylrestes erfolgt bei dieser Temperatur be deutend schneller. Aufarbeitung des Verfah rensproduktes wie im Beispiel 1 geschildert.
Die neue Verbindung bildet sechsseitige Prismen. Sie zersetzt sich beim Erhitzen ohne zu schmelzen, ist leicht löslich in heissem Py- ridin, ziemlich gut löslich in kapern Pyridin und heissem Wasser, wenig löslich' in kaltem Wasser, in Alkohol und Azeton.
Process for the preparation of a salt of a derivative of 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, which can be obtained by replacing the hydrogen atom of its sulfonamide group with calcium, has the above-mentioned therapeutic properties to a greater extent than the corresponding hydrogen compound. also has a better tolerability and, as can be seen from the clinical examinations,
likely to have 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 -acylamino-benzenesulfonylamino-) pyridine is treated with a solution of calcium hydroxide, saponification of the acyl group and replacement of the hydrogen atom on the amido nitrogen with calcium the di- [2- (p-aminobenzenesulfonylamino-)
pyridine] calcium is formed. <I> 1st </I> embodiment example: 5 g 2- (p-acetylaminobenzene-sulfonylamino-) - pyridine are boiled for 35 hours with a solution of 5 g calcium hydroxide in 250 cm3 water.
The di - [2 - (p - aminobenzenesulfonylamino) pyridine] calcium, which crystallizes out on cooling, is collected; the yield is 5 g and can be increased by narrowing the mother liquor. The cleaning is done by recrystallization from hot water.
<I> 2nd </I> exemplary embodiment: 5 g of 2- (p-acetylaminobenzene-sulfonylamino-) - pyridine are heated to 130 C for 10 hours with a solution of 5 g of potassium hydroxide in 250 cm of water. The hydrolysis of the acetyl radical takes place significantly faster at this temperature. Work-up of the process product as described in Example 1.
The new connection forms six-sided prisms. It decomposes on heating without melting, is easily soluble in hot pyridine, fairly soluble in large 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 |
|---|---|---|---|
| CH213816T | 1943-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH213816A true CH213816A (en) | 1941-03-15 |
Family
ID=4448416
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH213816D CH213816A (en) | 1943-06-23 | 1939-11-21 | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH213816A (en) |
-
1939
- 1939-11-21 CH CH213816D patent/CH213816A/en unknown
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