DE172932C - - Google Patents
Info
- Publication number
- DE172932C DE172932C DENDAT172932D DE172932DA DE172932C DE 172932 C DE172932 C DE 172932C DE NDAT172932 D DENDAT172932 D DE NDAT172932D DE 172932D A DE172932D A DE 172932DA DE 172932 C DE172932 C DE 172932C
- Authority
- DE
- Germany
- Prior art keywords
- sodium
- theobromine
- formate
- diuretic
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
Links
- HLBBKKJFGFRGMU-UHFFFAOYSA-M Sodium formate Chemical compound [Na+].[O-]C=O HLBBKKJFGFRGMU-UHFFFAOYSA-M 0.000 claims description 5
- 239000004280 Sodium formate Substances 0.000 claims description 5
- 235000019254 sodium formate Nutrition 0.000 claims description 5
- -1 sodium theobromine sodium formate Chemical compound 0.000 claims description 4
- 239000007864 aqueous solution Substances 0.000 claims description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- YAPQBXQYLJRXSA-UHFFFAOYSA-N Theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 18
- 229960004559 Theobromine Drugs 0.000 description 9
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
- 230000001396 anti-anti-diuretic Effects 0.000 description 7
- 230000001882 diuretic Effects 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 4
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 4
- 239000002934 diuretic Substances 0.000 description 4
- OZHPKSFNBCNLER-UHFFFAOYSA-M sodium;3,7-dimethyl-6-oxopurin-2-olate Chemical compound [Na+].CN1C(=O)[N-]C(=O)C2=C1N=CN2C OZHPKSFNBCNLER-UHFFFAOYSA-M 0.000 description 4
- 208000004880 Polyuria Diseases 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000019253 formic acid Nutrition 0.000 description 3
- 231100000486 side effect Toxicity 0.000 description 3
- 229960004025 sodium salicylate Drugs 0.000 description 3
- PUZIEUCZZUYNJQ-UHFFFAOYSA-M N1C(=O)N(C)C=2N=CN(C)C2C1=O.C(=O)[O-].[Na+] Chemical compound N1C(=O)N(C)C=2N=CN(C)C2C1=O.C(=O)[O-].[Na+] PUZIEUCZZUYNJQ-UHFFFAOYSA-M 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N Xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drugs Drugs 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229960004889 salicylic acid Drugs 0.000 description 2
- 210000003734 Kidney Anatomy 0.000 description 1
- 229910020936 NaC Inorganic materials 0.000 description 1
- 231100000614 Poison Toxicity 0.000 description 1
- ZDPALFHDPFYJDY-UHFFFAOYSA-N [Na].OC=O Chemical compound [Na].OC=O ZDPALFHDPFYJDY-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 230000002378 acidificating Effects 0.000 description 1
- 230000000875 corresponding Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000003522 irritant Effects 0.000 description 1
- 231100000021 irritant Toxicity 0.000 description 1
- 239000002085 irritant Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003000 nontoxic Effects 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000000607 poisoning Effects 0.000 description 1
- 231100000572 poisoning Toxicity 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- HBRJTAOFEGTXSY-UHFFFAOYSA-M sodium;2-(3,7-dimethyl-2,6-dioxopurin-1-yl)acetate Chemical compound [Na+].CN1C(=O)N(CC([O-])=O)C(=O)C2=C1N=CN2C HBRJTAOFEGTXSY-UHFFFAOYSA-M 0.000 description 1
- WSRBRQQGWDWSON-UHFFFAOYSA-M sodium;3,7-dimethylpurine-2,6-dione;2-hydroxybenzoate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O.CN1C(=O)NC(=O)C2=C1N=CN2C WSRBRQQGWDWSON-UHFFFAOYSA-M 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- C07D473/12—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3 with methyl radicals in positions 1, 3, and 7, e.g. caffeine
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
KLASSE 12/λ GRUPPECLASS 12 / λ GROUP
Theobromin wirkt bekanntlich im Vergleich mit den übrigen Xanthinbasen in hervorragendem Maße ditiretisch; seiner Verwendung steht aber im Wege, daß es unangcnehme Nebenwirkungen hat und, namentlich in größeren Dosen, selbst leichte Vergiftungs-. erscheinungen zeigt. Dann ist auch besonders seine Schwerlöslichkeit im Wasser für seine Verwendung als Diuretikurh hinderlich.As is well known, theobromine has an excellent ditiretic effect in comparison with the other xanthine bases; but its use stands in the way that it is unpleasant Has side effects and, especially in larger doses, even mild poisoning. shows appearances. Then its poor solubility in water is also particularly important its use as a diuretic is a hindrance.
ίο Wenn die Schwerlöslichkeit durch Herstellung von gemischten Salzen (Doppelsalzen) auch aufgehoben werden kann, so wird hierdurch andererseits die diuretische Wirkung infolge der Vergrößerung des Moleküls wieder verringert, wie sich dies z. B. beim Theobrominnatriumsalicylat zeigt. Nun liegt aber in der Ameisensäure (vergl. Compendium der Arzneiverordnung von Liebreich und Langgaard, Berlin 1896, S. 23) und dementsprechend auch im Natriumformiat bereits ein ungiftiges Diuretikum vor, was zu Versuchen '. zur Darstellung des Doppelsalzes Theobrominnatrium-Natriumformiat .Veranlassung gab.ίο If the poor solubility by manufacturing can also be canceled by mixed salts (double salts), this is how on the other hand, the diuretic effect is reduced again as a result of the enlargement of the molecule, how this z. B. in theobromine sodium salicylate shows. But now lies in the Formic acid (see Compendium of the Drug Ordinance von Liebreich and Langgaard, Berlin 1896, p. 23) and accordingly also in sodium formate non-toxic diuretic what to try '. for the representation of the double salt theobromine sodium sodium formate . Cause.
ag Beispiel: ag example:
Für die Darstellung der reinen Verbindung geht man von reinem Theobrominnatrium und reinem ameisensauren Natrium aus. Zur Gewinnung des ersteren wird Theobromin inPure theobromine sodium is used to represent the pure compound and pure sodium formic acid. To obtain the former, theobromine is used in
einem geringeren Überschuß der berechneten Menge Natronlauge gelöst und die filtrierte Lösung mit dem 6- bis 8 fachen Volumen Alkohol versetzt; das ausgeschiedene Theobrominnatrium wird abgesaugt, mit Alkohol nachgewaschen und getrocknet. Zur Darstellung von wasserfreiem Natriumformiat neutralisiert man am besten starke Natronlauge rtfit Ameisensäure bis zur schwach sauren Reaktion, dampft die filtrierte Lösung vollständig ein und trocknet den Rückstand' bei I2O° C. .dissolved in a smaller excess of the calculated amount of sodium hydroxide solution and filtered 6 to 8 times the volume of alcohol is added to the solution; the excreted theobromine sodium is suctioned off, washed with alcohol and dried. For representation The best way to neutralize anhydrous sodium formate is strong sodium hydroxide solution, rtfit formic acid to weak acidic reaction, the filtered solution evaporates completely and dries the residue ' at I2O ° C.
Zur Darstellung des Theobrominnatrium-Natriumformiats werden 70,1 Teile Theobrominnatrium (entsprechend 62,5 Teilen Theobromin) in 200 Teilen Wasser gelost, worauf man eine Lösung von 23,5 Teilen wasserfreiem Natriumformiat in 50 Teilen Wasser zugibt und das Gemisch nach dem Filtrieren auf dem Dampfbade zur Trockne verdampft. Das so erhaltene Doppelsalz entspricht der FormelTo prepare the theobromine sodium sodium formate, 70.1 parts of theobromine sodium are used (corresponding to 62.5 parts of theobromine) dissolved in 200 parts of water, whereupon one a solution of 23.5 parts of anhydrous Sodium formate in 50 parts of water is added and the mixture is filtered evaporated to dryness on the steam bath. The double salt thus obtained corresponds to formula
NaC1 NaC 1 H1 Nt O2 + H 1 Nt O 2 + Na N / A O OC H + H2 OO OC H + H 2 O
und enthält 63,5 Prozent Theobromin, 23,5 Prozent wasserfreies Natriumformiat und 6,4 Prozent Wasser. Es ist ein weißes, salzig bitter schmeckendes Pulver, daß sich leicht mit alkalischer Reaktion in Wasser löst und dem Theobromin gegenüber sich dadurch auszeichnet, daß es nicht giftig ist. Aus seiner wäßrigen Lösung wird durch Essigsäure Theobromin ausgefällt; im Filtrate ist die Ameisensäure durch Reduktion von Silbernitrat nachweisbar.and contains 63.5 percent theobromine, 23.5 percent sodium formate anhydrous, and 6.4 percent Water. It is a white, salty bitter tasting powder that is easy to use alkaline reaction dissolves in water and is distinguished from theobromine by that it is not poisonous. Acetic acid is added to its aqueous solution Theobromine precipitated; The formic acid is in the filtrate due to the reduction of silver nitrate verifiable.
Das Theobrominnatrium - Natriumformiat soll als Diuretikum Anwendung finden.Theobromine sodium formate is said to be used as a diuretic.
Bekannt sind bereits das Thcobromin-Natriosalicylicum (eine Verbindung von Theobrominnatrium mit Natriumsalicylat, die unter dem Namen »Diuretin« in den Handel ge--7o langt; vergl. Hager's Handb. der pharm. Praxis, Neue Bearb., 4. Abdr., Bd. II, S. 1043)The thcobromine natriosalicylicum (a compound of theobromine sodium with sodium salicylate, which is marketed under the name "Diuretin" suffices; cf. Hager's handbook of pharm. Practice, New Editing, 4th Abdr., Vol. II, p. 1043)
und das Thcobromin-Natriumsalicylat (eine Verbindung von Thcobromin mit Natriumsalicylat). Mit Herstellung dieser Verbindungen ist zwar der Effekt errcipht worden, das Theobromin leichter löslich in Wasser zu machen, doch haben diese Salze infolge ihres Gehaltes an Salicylsäure den Nachteil einer Reizwirkung auf die Nieren, wie eine solche schon mehrfach bei Salicylsäurebehandlung beobachtet worden ist (vergl. Lüthje, Dtsch. Archiv für klinische Medizin, Bd. 74, Jahrg. 1902, und Brugsch, Therapie der Gegenwart 1904, Heft 2). Von dieser häßlichen Nebenwirkung ist das Theobrominnatrium-Natriumformiat völlig frei. Demand the thcobromine sodium salicylate (a Connection of thcobromine with sodium salicylate). By making these connections it is true that the effect has been achieved that theobromine is more readily soluble in water to make, but these salts have the disadvantage due to their salicylic acid content an irritant effect on the kidneys, as has been the case several times with salicylic acid treatment has been observed (see Lüthje, German Archive for Clinical Medicine, Vol. 74, Year 1902, and Brugsch, Therapy of the Present 1904, Issue 2). From this ugly one As a side effect, theobromine sodium sodium formate is completely free. To the
■'·. Agurine einer Doppclverbindung1 aus Theobrominnatrium und Natriumacetat gegenüber (vcrgl. Merck's Jahrcsbcr. 1901, 8.51), das zwar infolge seines höheren 'flicobromingchaltes stärker diuretisch wirkt als das Diuretin und das Thcobromin-Natriumsalicylat,■ '·. Agurine of a double compound 1 made from sodium theobromine and sodium acetate (cf.
besitzt die neue Verbindung durch die Einführung einer zweiten, ebenfalls diuretisch wirkenden Komponente in das Theobrominmolekül den Vorteil einer sehr wesentlich 25 größeren diuretischcn Wirkung. Das Theobrominnatrium-Natriumformiat übertrifft eben alle bisher für therapeutische Zwecke benutzten Theobromindoppelsalze in der Stärke der diuretischen Wirkung und steht keinem 30 derselben hinsichtlich Wasserlöslichkeit und dem Fehlen von schädlichen Nebenwirkungen nach.possesses the new connection through the introduction of a second, also diuretic acting component in the theobromine molecule has the advantage of a very substantial 25 greater diuretic effect. Sodium theobromine formate Exceeds all theobromine double salts previously used for therapeutic purposes in strength the diuretic effect and is not equivalent to any of the same in terms of water solubility and the absence of harmful side effects.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE172932C true DE172932C (en) |
Family
ID=437781
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT172932D Active DE172932C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE172932C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE944518C (en) * | 1950-08-20 | 1956-06-14 | Byk Gulden Lomberg Chem Fab | Process for the preparation of solutions of xanthines substituted in the 1,3-position |
-
0
- DE DENDAT172932D patent/DE172932C/de active Active
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE944518C (en) * | 1950-08-20 | 1956-06-14 | Byk Gulden Lomberg Chem Fab | Process for the preparation of solutions of xanthines substituted in the 1,3-position |
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