CH221518A - 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
- CH221518A CH221518A CH221518DA CH221518A CH 221518 A CH221518 A CH 221518A CH 221518D A CH221518D A CH 221518DA CH 221518 A CH221518 A CH 221518A
- Authority
- CH
- Switzerland
- Prior art keywords
- calcium
- preparation
- aminobenzenesulfonamide
- salt
- derivative
- Prior art date
Links
- 238000002360 preparation method Methods 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
- 238000000034 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
- 229910052791 calcium Inorganic materials 0.000 claims description 7
- 239000011575 calcium Substances 0.000 claims description 6
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 201000009910 diseases by infectious agent Diseases 0.000 claims description 3
- 125000004435 hydrogen atoms Chemical group [H]* 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
- 238000007127 saponification reaction Methods 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L Calcium hydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims 1
- 206010035664 Pneumonia Diseases 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
- 125000003368 amide group Chemical group 0.000 claims 1
- 239000000920 calcium hydroxide Substances 0.000 claims 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- -1 hydrogen compound Chemical class 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- MAQAGRJURDEYDQ-UHFFFAOYSA-N 6-methylpyridine Chemical compound CC1=C=CC=C[N]1 MAQAGRJURDEYDQ-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000009835 boiling Methods 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 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
- 239000002699 waste material Substances 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 Abhöminlings des p-Aminobenzolsulfonamids. Das in neuester Zeit bekannt gewordene 2 - (p-AminobenzoLlsulfonylamino-) 6 -methyl- pyridin hat sich allgeeignet 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- ziumealz desi 2 - (p - Aminobenzolaulfonyl- a.mino-) 6-methyl.pyridinsi :
gegenüber der ent sprechenden Wasserstoffverbindung die oben erwähnten therapeutischen Eigenschaften in verstärktem Masse aufweiset und ausserdem eine bessere Verträglichkeit besitzt. Die neue Verbindung soll daher zur Bekämpfung in- fektiöser Erkrankungen, speziell- der durch Strepto-, Gono- und Pneumokokken verur sachten, verwendet werden.
Dass erfindungsgemässe Verfahren zur Darstellung der neuen Verbindung ist @da- durch gekennzeichnet, dass man 2-(p-Acyl- aminobenzalsu#l!fonyda.mino-) 6 -m@ethylpyridin mit einer Lösung von Kalziumhydrogyd be handelt,
wobei durch Verseifung der Ac3l- gruppe und Ersatz des @am Amidostickstoff sitzenden Wasserstoffatoms @d'urch Kalzium das Di-[2-(p-Aminobenzolsulfonylamino-) 6- m,ethylpyridinl-Kalziumentsteht.
Ausf üdarwngsbeispiel: 5 g 2 - (p - AcetylaminobenzoIsiul.fonyl - amino-) 6 -m#e#thylpy.ridin werden mit einer Lösung von 7 g Kallziumhydrogyd in 350 cm' Wasser 40 Stunden verkocht. Das. beim Ab kühlen :auskristallisierende Di-[2-(p-Amino- benzolsulfonylamino-) 6-methylpyri:dinl-gal- zium wird :gesammelt;
die Ausbeute beträgt 5,5 g und kann durch Einengen der Mutter lauge erhöht werden. Die Reinigung erfolgt durch Umkristallisieren aus heissem Wasser.
Die neue Verbindung kristallisiert in schönen Prismen. Sie zersetzt sieh oberhalb <B>250'C</B> ohne zu :schmelzen, ist ,gut löslich in heissem Wasser und Pyridin, weniger löslich in kaltem Wasser und Alkohol, schwerlöslich in Azeton, Äther und Benzol.
Process for the preparation of a salt of a p-aminobenzenesulfonamide waste. The recently known 2- (p-aminobenzoLlsulfonylamino) 6 -methylpyridine has proven to be universally suitable for combating infectious diseases, in particular those caused by cocci.
It has now been found that the calcium alkali obtainable by replacing the hydrogen atom of its sulfonamide group with calcium desi 2 - (p - aminobenzolaulfonyl- a.mino-) 6-methyl.pyridinsi:
has the above-mentioned therapeutic properties to a greater extent than the corresponding hydrogen compound and also has better tolerability. The new compound is therefore intended to be used to combat infectious diseases, especially those caused by streptococci, gonococci and pneumococci.
The method according to the invention for the preparation of the new compound is characterized in that 2- (p-acylaminobenzalsu # l! Fonyda.mino-) 6 -m @ ethylpyridine is treated with a solution of calcium hydrogen,
where by saponification of the Ac3l group and replacement of the hydrogen atom on the amido nitrogen with calcium, the di- [2- (p-aminobenzenesulfonylamino) 6- m, ethylpyridinio-calcium is formed.
Ausf üdarwngsbeispiel: 5 g of 2- (p-acetylaminobenzoIsiul.fonyl-amino-) 6 -m # e #thylpy.ridin are boiled with a solution of 7 g of calcium hydrogen in 350 cm 'of water for 40 hours. The. on cooling: di- [2- (p-aminobenzenesulfonylamino-) 6-methylpyri: dinl-gal- zium which crystallizes out is: collected;
the yield is 5.5 g and can be increased by concentrating the mother liquor. The cleaning is done by recrystallization from hot water.
The new connection crystallizes in beautiful prisms. It decomposes above <B> 250'C </B> without: melting, is, readily soluble in hot water and pyridine, less soluble in cold water and alcohol, sparingly soluble in acetone, ether and benzene.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH221518T | 1939-11-21 | ||
| CH213816T | 1943-06-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH221518A true CH221518A (en) | 1942-05-31 |
Family
ID=25725502
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH221518D CH221518A (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) | CH221518A (en) |
-
1939
- 1939-11-21 CH CH221518D patent/CH221518A/en unknown
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