CH149920A - Process for the preparation of a compound from calcium nitrite and theobromine. - Google Patents
Process for the preparation of a compound from calcium nitrite and theobromine.Info
- Publication number
- CH149920A CH149920A CH149920DA CH149920A CH 149920 A CH149920 A CH 149920A CH 149920D A CH149920D A CH 149920DA CH 149920 A CH149920 A CH 149920A
- Authority
- CH
- Switzerland
- Prior art keywords
- theobromine
- compound
- calcium
- calcium nitrite
- nitrite
- Prior art date
Links
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 title claims description 18
- RAFRTSDUWORDLA-UHFFFAOYSA-N phenyl 3-chloropropanoate Chemical compound ClCCC(=O)OC1=CC=CC=C1 RAFRTSDUWORDLA-UHFFFAOYSA-N 0.000 title claims description 9
- 229960004559 theobromine Drugs 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000000920 calcium hydroxide Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 3
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 5
- 235000011116 calcium hydroxide Nutrition 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- ZRMDPUXBTGYVAR-UHFFFAOYSA-N calcium;3,7-dimethylpurine-2,6-dione Chemical compound [Ca].CN1C(=O)NC(=O)C2=C1N=CN2C ZRMDPUXBTGYVAR-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002826 nitrites Chemical class 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 208000031872 Body Remains Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- BRPQOXSCLDDYGP-UHFFFAOYSA-N calcium oxide Chemical compound [O-2].[Ca+2] BRPQOXSCLDDYGP-UHFFFAOYSA-N 0.000 description 1
- 239000000292 calcium oxide Substances 0.000 description 1
- ODINCKMPIJJUCX-UHFFFAOYSA-N calcium oxide Inorganic materials [Ca]=O ODINCKMPIJJUCX-UHFFFAOYSA-N 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000013341 scale-up Methods 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Herstellung einer Verbindung aus Caleiumnitrit und Theobromin. Von den anorganischen Nitriten wird bis her nur das durch starke Gefässwirkung aus gezeichnete Natriumnitrit in grösserem Um fang benutzt. Die Erfindung erstrebt die Anwendung von Calciumnitrit, und zwar in Verbindung mit Theobromin.
Das Theobromin liefert kein eindeutig zu charakterisierendes Doppelsalz mit Calcium- nitrit. Es wurde jedoch gefunden, dass man ein solches erhält, wenn man Theobromin, Calciumnitrit und Calciumhydroxyd bei Ge genwart von Wasser gleichzeitig aufeinander einwirken lässt und die Lösung zur Trockne eindampft. Beim Eindampfen der Lösung hinterbleibt ein wasserlöslicher und luft beständiger Körper. Die unter gelindem Er wärmen entstehende Lösung wird gegebenen falls, um geringe Mengen von Karbonat zu beseitigen, filtriert und dann vorteilhaft im Vakuum zur Trockne verdampft.
Der so erhaltene Körper kann als Verbin dung angesprochen werden. Wenn der Kör per nicht sehr stabil ist und unter bestimm- ten Bedingungen wieder in die Komponen ten zerlegt werden kann, so lässt sich doch der Charakter einer Verbindung einwandfrei nachweisen. Versetzt man Theobromincal- cium mit wechselnden Mengen überschüssi gen Calciumnitrits, dampft zur Trockne ein und extrahiert im Soxhletapparat mit Alko hol, so hinterbleibt in jedem Falle ein Stoff, ' der ein Molekül Theobromincalcium und ein Molekül Calciumnitrit enthält.
Er wird,durch Alkohol nicht aufgespalten und nicht gelöst, während Calciumnitrit allein unter gleichen Bedingungen glatt gelöst wird.
Der so gewonnene Stoff stellt eine weisse, feinpulverige Substanz dar, die in Wasser löslich, in organischen Lösungsmitteln schwer löslich ist. Versetzt man die wässerige Lö sung tropfenweise mit einer Mineralsäure, so wird salpetrige Säure in Freiheit gesetzt, während Theobromin aus der Lösung aus fällt.
In pharmakologischer Beziehung zeigt der genannte Körper neuartige Effekte. Nach .einem besonderen Verfahren gelingt es, Ka ninchen zu einer chronischen Hypertonie von etwa 180 mm HK-Druck zu bringen, bei denen diese Hypertonie wochenlang anhält. Im Gegensatz zu der rasch abklingenden Wirkung der Alkalinitrite konnte bei An wendung der beschriebenen Komplexverbin dung an den hypertonischen Versuchstieren eine sehr nachhaltige, stundenlang dauernde Senkung um etwa 40 mm Hg bewirkt wer den.
<I>Beispiel:</I> 36 Teile Theobromin, 7,4 Teile Calcium- hydroxyd als Kalkmilch (oder 5,6 Teile Cal ciumoxyd und 100 Teile Wasser) und 15 Teile Calciumnitrit werden zusammengege ben. Es tritt Auflösung ein. Nach dem Fil trieren wird die blanke Lösung im Vakuum zur Trockne gebracht. Die Verbindung ist gut in Wasser löslich "und nach scharfem Trocknen luftbeständig.
Process for the preparation of a compound from calium nitrite and theobromine. Of the inorganic nitrites, only sodium nitrite, which has a strong vascular effect, has been used on a large scale up to now. The invention seeks the use of calcium nitrite in conjunction with theobromine.
The theobromine does not provide a double salt with calcium nitrite that can be clearly characterized. However, it has been found that such a product is obtained if theobromine, calcium nitrite and calcium hydroxide are allowed to act on one another at the same time in the presence of water and the solution is evaporated to dryness. When the solution evaporates, a water-soluble and air-resistant body remains. The resulting solution is heated, if necessary, to remove small amounts of carbonate, filtered and then advantageously evaporated to dryness in a vacuum.
The body obtained in this way can be addressed as a connec tion. If the body is not very stable and can be broken down into its components again under certain conditions, the character of a connection can still be clearly demonstrated. If theobromine calcium is mixed with varying amounts of excess calcium nitrite, evaporated to dryness and extracted with alcohol in the Soxhlet apparatus, what remains in each case is a substance which contains one molecule of theobromine calcium and one molecule of calcium nitrite.
It is not broken down or dissolved by alcohol, whereas calcium nitrite alone is smoothly dissolved under the same conditions.
The substance obtained in this way is a white, finely powdered substance that is soluble in water and sparingly soluble in organic solvents. If a mineral acid is added dropwise to the aqueous solution, nitrous acid is set free, while theobromine precipitates out of the solution.
From a pharmacological point of view, said body shows novel effects. A special procedure succeeds in bringing rabbits to chronic hypertension of around 180 mm HD pressure, where this hypertension lasts for weeks. In contrast to the rapidly decaying effect of the alkali nitrites, when the complex compound described was applied to the hypertonic test animals, a very sustained, hour-long reduction of about 40 mm Hg was achieved.
<I> Example: </I> 36 parts of theobromine, 7.4 parts of calcium hydroxide as milk of lime (or 5.6 parts of calcium oxide and 100 parts of water) and 15 parts of calcium nitrite are combined. Dissolution occurs. After filtering, the bare solution is brought to dryness in vacuo. The compound is readily soluble in water and air-resistant after thorough drying.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE149920X | 1928-05-07 | ||
| CH142595T | 1929-04-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH149920A true CH149920A (en) | 1931-09-30 |
Family
ID=25714097
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH149920D CH149920A (en) | 1928-05-07 | 1929-04-17 | Process for the preparation of a compound from calcium nitrite and theobromine. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH149920A (en) |
-
1929
- 1929-04-17 CH CH149920D patent/CH149920A/en unknown
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