CH199671A - Process for the preparation of a double compound from 3,5-dimethylisoxazole-4-carboxylic acid diethylamide and calcium salicylate. - Google Patents
Process for the preparation of a double compound from 3,5-dimethylisoxazole-4-carboxylic acid diethylamide and calcium salicylate.Info
- Publication number
- CH199671A CH199671A CH199671DA CH199671A CH 199671 A CH199671 A CH 199671A CH 199671D A CH199671D A CH 199671DA CH 199671 A CH199671 A CH 199671A
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethylisoxazole
- carboxylic acid
- acid diethylamide
- calcium salicylate
- double compound
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 12
- AVVIDTZRJBSXML-UHFFFAOYSA-L calcium;2-carboxyphenolate;dihydrate Chemical compound O.O.[Ca+2].OC1=CC=CC=C1C([O-])=O.OC1=CC=CC=C1C([O-])=O AVVIDTZRJBSXML-UHFFFAOYSA-L 0.000 title claims description 9
- NFALFEDRJGVKNY-UHFFFAOYSA-N n,n-diethyl-3,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound CCN(CC)C(=O)C=1C(C)=NOC=1C NFALFEDRJGVKNY-UHFFFAOYSA-N 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 4
- UZBQIPPOMKBLAS-UHFFFAOYSA-N diethylazanide Chemical compound CC[N-]CC UZBQIPPOMKBLAS-UHFFFAOYSA-N 0.000 claims description 4
- 239000003814 drug 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
- 235000009508 confectionery Nutrition 0.000 claims description 2
- 235000019640 taste Nutrition 0.000 claims description 2
- 239000002253 acid Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-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
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 150000003334 secondary amides Chemical class 0.000 description 2
- IJEUISLJVBUNRE-UHFFFAOYSA-N 3,5-dimethyl-1,2-oxazole-4-carboxylic acid Chemical compound CC1=NOC(C)=C1C(O)=O IJEUISLJVBUNRE-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000003118 aryl group Chemical class 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 159000000007 calcium salts Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 235000019643 salty taste Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
Verfahren zur Herstellung einer Doppelverbindung aus 3,5-Dimethylisoaazol- 4-ssarbonsäurediäthylamid und Calciumsalieylat. Es wurde gefunden, dass die als Arznei mittel wertvollen sekundären Amide von Isoxazolearbonsäuren (Patent Nr.<B>185280)</B> mit Calciumsalzen aromatiscber Oxysäuren sowie mit Caleiumrhodanid kristallisierte Doppel verbindungen zu bilden vermögen.
Die Be deutung dieser neuen Doppelverbindungen besteht vor allem darin, dass die zumeist flüssigen oder tief schmelzenden sekundären Amide der 3,5-Dimethylisoxazol-4-carbonsäure in feste, beständige Körper übergeführt werden. Als weiterer Vorteil der neuen Verbindungen ist hervorzuheben, dass der bittere bezw. salzige Geschmack der Ausgangsstoffe durch die Ver bindung mit Caleiumsalzen herabgesetzt wird, oft ganz verschwindet.
Die Darstellung der neuen Verbindungen kann durch Zusammenbringen der Kompo nenten in geeigneten Lösungsmitteln erfolgen. Dabei kristallisiert die Doppelverbindung häufig unmittelbar aus, oder sie wird durch Zusatz anderer Lösungsmittel, in denen sie schwer löslich ist, ausgefällt. Sie kann auch durch Abdampfen des Lösungsmittels ge wonnen werden. Statt das Caleiumsalz als solches zu verwenden, kann dieses auch in der Lösung, z. B. aus Calciumcarbonat und der Säure, unmittelbar gebildet werden.
Gegenstand des vorliegenden Patentes ist ein Verfahren zur Herstellung einer Doppel verbindung aus 3,5-Dimethylisoxazol-4-car- bonsäurediäthylamid und Calciumsalicylat, welches dadurch gekennzeichnet, dass man auf 3,5 -Dimethylisoxazol -4- carbonsäurediäthyl- amid Caloiumsalieylat einwirken lässt.
Die neue Doppelverbindung aus 3,5 -Di- methylisoxazol-4-earbonsäurediäthylamid und Caleiumsalicylat krisallisiert in Prismen. Sie ist leicht löslich in Alkohol, mässig löslich in Wasser, schmeckt schwach süsslich und soll alä Arzneimittel verwendet werden. Beispiel: 196 Teile 3,5-Dimethylisoxazol-4-carbon- säurediäthylamid werden mit 2000 Teilen Wasser und 278 Teilen trockenem Calcium- salicylat auf dein Dampfbad erwärmt, bis alles gelöst ist.
Beim Eindampfen kristallisiert die Doppelverbindung aus einem Mol Calcium- salicylat und einem Mol 3,5-Dimethyliaoxazol- 4-carbonsäurediäthylamid in Prismen aus.
Process for the preparation of a double compound from 3,5-dimethylisoaazole-4-ssarboxylic acid diethylamide and calcium salylate. It has been found that the secondary amides of isoxazolearboxylic acids (patent no. 185280), which are valuable as medicaments, are able to form double compounds crystallized with calcium salts of aromatic oxyacids and with calcium rhodanide.
The main importance of these new double compounds is that the mostly liquid or low-melting secondary amides of 3,5-dimethylisoxazole-4-carboxylic acid are converted into solid, stable bodies. Another advantage of the new compounds should be emphasized that the bitter or. The salty taste of the raw materials is reduced by the connection with Caleium salts, often disappears completely.
The preparation of the new compounds can be done by bringing the components together in suitable solvents. The double compound often crystallizes out immediately, or it is precipitated by adding other solvents in which it is sparingly soluble. It can also be obtained by evaporating the solvent. Instead of using the Caleiumsalz as such, this can also be in the solution, e.g. B. from calcium carbonate and the acid, are formed directly.
The subject of the present patent is a process for the preparation of a double compound from 3,5-dimethylisoxazole-4-carboxylic acid diethylamide and calcium salicylate, which is characterized in that calcium salicylate is allowed to act on 3,5-dimethylisoxazole-4-carboxylic acid diethyl amide.
The new double compound of 3,5-dimethylisoxazole-4-carboxylic acid diethylamide and calcium salicylate crystallizes in prisms. It is easily soluble in alcohol, moderately soluble in water, tastes slightly sweet and should be used as a medicine. Example: 196 parts of 3,5-dimethylisoxazole-4-carboxylic acid diethylamide are heated in a steam bath with 2000 parts of water and 278 parts of dry calcium salicylate until everything has dissolved.
On evaporation, the double compound crystallizes from one mole of calcium salicylate and one mole of 3,5-dimethyliaoxazole-4-carboxylic acid diethylamide in prisms.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE199671X | 1935-11-22 | ||
| CH190545T | 1936-09-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH199671A true CH199671A (en) | 1938-08-31 |
Family
ID=25722000
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH199671D CH199671A (en) | 1935-11-22 | 1936-09-09 | Process for the preparation of a double compound from 3,5-dimethylisoxazole-4-carboxylic acid diethylamide and calcium salicylate. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH199671A (en) |
-
1936
- 1936-09-09 CH CH199671D patent/CH199671A/en unknown
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