CH307798A - Process for the preparation of a salt of 4-amino-salicylic acid. - Google Patents
Process for the preparation of a salt of 4-amino-salicylic acid.Info
- Publication number
- CH307798A CH307798A CH307798DA CH307798A CH 307798 A CH307798 A CH 307798A CH 307798D A CH307798D A CH 307798DA CH 307798 A CH307798 A CH 307798A
- Authority
- CH
- Switzerland
- Prior art keywords
- salt
- amino
- pyridine
- salicylic acid
- carboxylic acid
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims description 19
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 title claims description 15
- 229960004909 aminosalicylic acid Drugs 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 9
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 claims description 9
- 230000001476 alcoholic effect Effects 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 230000001419 dependent effect Effects 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- -1 alkali metal salt Chemical class 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- BAQLNPIEFOYKNB-UHFFFAOYSA-N pyridine-2-carbohydrazide Chemical compound NNC(=O)C1=CC=CC=N1 BAQLNPIEFOYKNB-UHFFFAOYSA-N 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung eines Salzes der 4-Amino-salicylsäure. Gegenstand der vorliegenden Erfindung ist ein Verfahren zur Herstellung eines neuen Salzes der 4-Amino-salicylsäure, dem die fol gende Strukturformel zukommt
EMI0001.0005
Das Verfahren gemäss der vorliegenden Er findung ist dadurch gekennzeichnet, dass 4- Amiiio-salicylsäure oder eines ihrer Salze mit Pyridin-4-carbonsäurehydrazid oder einem Salz desselben zur Umsetzung gebracht wird.
Das dabei erhaltene neue Salz ist eine schwach gelb gefärbte, kristalline Verbindung, die sich bei Temperaturen über 134 C unter Gasentwicklung zersetzt. Das neue Salz besitzt wertvolle therapeutische Eigenschaften; es ist insbesondere gegen Tuberkulose wirksam und soll deshalb als Heilmittel verwendet werden.
Zur Durchführung des Verfahrens gemäss der Erfindung kann man 4-Amino-salicylsäure mit Pyridin-4-carbonsäurehydrazid in alkoholi scher Lösung zur Reaktion bringen. Statt der freien 4-Amino-salicylsäure und dem freien 1'yridin-4-carbonsäurehydrazid kann man ein Salz der 4-Amino-salicylsäure, z. B. ein Alkali metallsalz, mit einem Salz des Pyridin-4-car- bonsäurehydrazids, z. B. dem Hydrochlorid, zur Umsetzung bringen.
Im letzteren Fall ist es zweckmässig, gesättigte wässrige Lösungen der genannten Salze herzustellen und diese Lösun- gen zu vermischen. Das Salz der 4-Amino- salicylsäure mit dem Pyridin-4-carbonsäure- hydrazid scheidet sich dabei in Form eines kri stallinen Niederschlages ab. <I>Beispiel 1:</I> Eine Lösung von 27,6 Gewichtsteilen Pyri- din-4-carbonsäurehydrazid in 500 Volumteilen 96%igem Alkohol wird auf einmal zu 30,6 Ge wichtsteilen fester 4-Amino-salicylsäure gege ben.
Es erfolgt sofortige Auflösung der 4- Amino-salicylsäure. Nach kurzer Zeit kri stallisiert das Salz der 4-Amino-salicylsäure mit dem Pyridin-4-earbonsäurehydrazyd in Form von schwach gelb gefärbten, feinen Nä- delchen aus, die abfiltriert und getrocknet werden.
Beispiel <I>2:</I> Die gesättigten wässrigen Lösungen glei cher Gewichtsteile des Natriumsalzes der p- Amino-salicylsäure und des Hydrochlorids von Pyridin-4-carbonsäurehydrazid werden zusammengegeben. Das Salz der 4-Amino- salicylsäure mit dem Pyridincarbonsäure- hydrazid kristallisiert spontan aus dem er haltenen Gemisch aus..
Process for the preparation of a salt of 4-amino-salicylic acid. The present invention relates to a process for the preparation of a new salt of 4-amino-salicylic acid, which has the following structural formula
EMI0001.0005
The process according to the present invention is characterized in that 4-amino-salicylic acid or one of its salts is reacted with pyridine-4-carboxylic acid hydrazide or a salt thereof.
The new salt obtained is a pale yellow colored, crystalline compound which decomposes at temperatures above 134 C with evolution of gas. The new salt has valuable therapeutic properties; it is particularly effective against tuberculosis and should therefore be used as a remedy.
To carry out the process according to the invention, 4-aminosalicylic acid can be reacted with pyridine-4-carboxylic acid hydrazide in an alcoholic solution. Instead of the free 4-aminosalicylic acid and the free 1'yridine-4-carboxylic acid hydrazide, a salt of 4-aminosalicylic acid, e.g. B. an alkali metal salt with a salt of pyridine-4-car- bonsäurehydrazids, z. B. the hydrochloride, bring to implementation.
In the latter case, it is advisable to prepare saturated aqueous solutions of the salts mentioned and to mix these solutions. The salt of 4-amino-salicylic acid with the pyridine-4-carboxylic acid hydrazide separates out in the form of a crystalline precipitate. <I> Example 1 </I> A solution of 27.6 parts by weight of pyridine-4-carboxylic acid hydrazide in 500 parts by volume of 96% alcohol is added all at once to 30.6 parts by weight of solid 4-aminosalicylic acid.
The 4-amino-salicylic acid dissolves immediately. After a short time, the salt of 4-aminosalicylic acid crystallizes out with the pyridine-4-carboxylic acid hydrazide in the form of pale yellow, fine needles which are filtered off and dried.
Example <I> 2: </I> The saturated aqueous solutions of equal parts by weight of the sodium salt of p-amino-salicylic acid and the hydrochloride of pyridine-4-carboxylic acid hydrazide are combined. The salt of 4-amino salicylic acid with the pyridine carboxylic acid hydrazide crystallizes spontaneously from the mixture obtained from ..
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH307798T | 1954-03-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH307798A true CH307798A (en) | 1955-06-15 |
Family
ID=4493280
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH307798D CH307798A (en) | 1954-03-06 | 1952-02-25 | Process for the preparation of a salt of 4-amino-salicylic acid. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH307798A (en) |
-
1952
- 1952-02-25 CH CH307798D patent/CH307798A/en unknown
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