CH221515A - 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
- CH221515A CH221515A CH221515DA CH221515A CH 221515 A CH221515 A CH 221515A CH 221515D A CH221515D A CH 221515DA CH 221515 A CH221515 A CH 221515A
- Authority
- CH
- Switzerland
- Prior art keywords
- pyridine
- salt
- derivative
- calcium
- soluble
- Prior art date
Links
- 238000000034 method Methods 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
- 150000003839 salts Chemical class 0.000 title claims description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
- -1 halogen salt Chemical class 0.000 claims description 7
- 229910052791 calcium Inorganic materials 0.000 claims description 5
- 239000011575 calcium Substances 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
- 150000001875 compounds Chemical class 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
- 201000009910 diseases by infectious agent Diseases 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000002844 melting Methods 0.000 claims description 2
- 230000001264 neutralization Effects 0.000 claims description 2
- 125000000565 sulfonamide group Chemical group 0.000 claims description 2
- FZERHIULMFGESH-UHFFFAOYSA-N Acetanilide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims 1
- XZYNLCBYJQOLTR-UHFFFAOYSA-N C(C)(=O)NC1=CC(=NC=C1)NS(=O)(=O)C1=CC=CC=C1 Chemical compound C(C)(=O)NC1=CC(=NC=C1)NS(=O)(=O)C1=CC=CC=C1 XZYNLCBYJQOLTR-UHFFFAOYSA-N 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 159000000007 calcium salts Chemical class 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
- CYLYVXPHAQLXFG-UHFFFAOYSA-N N-[4-(pyridin-2-ylsulfamoyl)phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1S(=O)(=O)NC1=CC=CC=N1 CYLYVXPHAQLXFG-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 125000004435 hydrogen atoms Chemical group [H]* 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
Description
Verfahren zur Darstellung eines Salzes eines Abkömmlings des p-Aminobenzolsulfonamids. Das in neuester Zeit bekannt .gewordene 2- (p-Acetyl',aminobenzolsulfonylamino-) pyri- .din hat sich als, geeignet erwiesen zur Be kämpfung infektiöser, insbesondere durch Kokken hervorgerufener Krankheiten.
Es wurde nun gefunden, dass das. durch Ersatz desi Wasserstoffatoms, seiner Sulfon- amidgruppe durch Kalzium erhältliche Kal- zium@salz des 2 - (p - Acetylaminobenzol.sul - fonylamino-)pyridins gegenüber der entspre chenden Wasserstoffverbindung die oben er wähnten therapeutischen Eigenschaften in verstärktem Masse aufweist, ausserdem eine bessere Verträglichkeit besitzt.
Die neue Ver bindung solli daher zur Bekämpfung infek tiöser Erkrankungen, speziell der durch Strepto-, Gono- und Pneumokokken ver- ursa.ehten, verwendet werden.
Das erfindungsgemässe Verfahren zur Darstellung der neuen Verbindung ist da durch gekennzeichnet, .dass man 2-(p-Acetyl- aminobenzodsü,Ifonylamino-)pyridin und eine zum Austausch des@asserstoffesder Sulfon- amidgruppe gegen Kalzium befähigte Ver bindung, z.
B. Kalziumhydrogyd, lösliches Kalziumealz, wie Kalziumchlorid, aufeinan der einwirken lässt, wobei sich d@asi neutrale Kalziumsalz des 2-(p-Acetylaminobenzol- sulfonylamino-)pyridins, bildet.
Ausführungsbeispiel: 20 g 2.-(p-Acetylaminobenzolsulfonyl- amino-)pyridin werden in stark konzentrier- tem, 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, nutseht das auskriibtallisierte 2 -(p-Acetylaminobenzolsulfonylamino-) pyri- ,din-Kalzium ab und wäseht es mit wenig kaltem Wasser. Die Ausbeute beträgt 16 g.
Die neue Verbindung bildet Prismen. Sie zersetzt sich oberhalb: 250 C, ohne zu schmel zen, ist sowohl in warmem als auch in kaltem Wasser ziemlich löslich, ebenfalls in Pyri- din, wenib löslich in Alkohol, schwerlöslich in Azeton, 3ther und Benzol.
Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. The recently known 2- (p-acetyl ', aminobenzenesulfonylamino) pyri- .din 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-acetylaminobenzene-sulfonylamino-) pyridine, obtainable by replacing the hydrogen atom, its sulfonamide group with calcium, has the above-mentioned therapeutic properties compared to the corresponding hydrogen compound has to a greater extent, also has a better tolerance.
The new compound should therefore be used to combat infectious diseases, especially those caused by streptococci, gonococci and pneumococci.
The inventive method for the preparation of the new compound is characterized by .that 2- (p-acetyl aminobenzodsü, ifonylamino) pyridine and a compound capable of exchanging the @ hydrogen sulfonamide group with calcium, eg.
B. calcium hydrogen, soluble calcium salt, such as calcium chloride, can act on one another, with the neutral calcium salt of 2- (p-acetylaminobenzene sulfonylamino) pyridine forming.
Exemplary embodiment: 20 g of 2 .- (p-acetylaminobenzenesulfonylamino) pyridine 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 2 - (p-acetylaminobenzenesulfonylamino) pyri-, din-calcium, which has been crystallized out, is then washed off with a little cold water. The yield is 16 g.
The new connection forms prisms. It 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 |
|---|---|---|---|
| CH221515T | 1939-11-21 | ||
| CH213815T | 1943-03-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221515A true CH221515A (en) | 1942-05-31 |
Family
ID=25725495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221515D CH221515A (en) | 1939-11-21 | 1939-11-21 | Process for the preparation of a salt of a derivative of p-aminobenzenesulfonamide. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH221515A (en) |
-
1939
- 1939-11-21 CH CH221515D patent/CH221515A/en unknown
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