DE406211C - Process for the preparation of easily soluble double salts from monomethyl-, dimethyl- and trimethylxanthines - Google Patents
Process for the preparation of easily soluble double salts from monomethyl-, dimethyl- and trimethylxanthinesInfo
- Publication number
- DE406211C DE406211C DEF51241D DEF0051241D DE406211C DE 406211 C DE406211 C DE 406211C DE F51241 D DEF51241 D DE F51241D DE F0051241 D DEF0051241 D DE F0051241D DE 406211 C DE406211 C DE 406211C
- Authority
- DE
- Germany
- Prior art keywords
- calcium
- monomethyl
- dimethyl
- double salts
- preparation
- 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.)
- Expired
Links
- 150000003839 salts Chemical class 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 5
- LCCDINSFSOALJK-UHFFFAOYSA-N 1,3,4-trimethylpurine-2,6-dione Chemical class O=C1N(C)C(=O)N(C)C2(C)N=CN=C21 LCCDINSFSOALJK-UHFFFAOYSA-N 0.000 title claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 4
- MKJXYGKVIBWPFZ-UHFFFAOYSA-L calcium lactate Chemical compound [Ca+2].CC(O)C([O-])=O.CC(O)C([O-])=O MKJXYGKVIBWPFZ-UHFFFAOYSA-L 0.000 claims description 5
- 239000001527 calcium lactate Substances 0.000 claims description 4
- 229960002401 calcium lactate Drugs 0.000 claims description 4
- 235000011086 calcium lactate Nutrition 0.000 claims description 4
- 229940043430 calcium compound Drugs 0.000 claims description 2
- 150000001674 calcium compounds Chemical class 0.000 claims description 2
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 6
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical class CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 4
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
- 229960004559 theobromine Drugs 0.000 description 4
- -1 theobromine sodium - sodium salicylate Chemical compound 0.000 description 4
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 3
- 229960005069 calcium Drugs 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 229910052791 calcium Inorganic materials 0.000 description 3
- SMHNUIFHMAGAFL-UHFFFAOYSA-N calcium;2-hydroxypropanoic acid Chemical compound [Ca].CC(O)C(O)=O SMHNUIFHMAGAFL-UHFFFAOYSA-N 0.000 description 3
- 230000001882 diuretic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QUNWUDVFRNGTCO-UHFFFAOYSA-N 1,7-dimethylxanthine Chemical compound N1C(=O)N(C)C(=O)C2=C1N=CN2C QUNWUDVFRNGTCO-UHFFFAOYSA-N 0.000 description 2
- LPHGQDQBBGAPDZ-UHFFFAOYSA-N Isocaffeine Natural products CN1C(=O)N(C)C(=O)C2=C1N(C)C=N2 LPHGQDQBBGAPDZ-UHFFFAOYSA-N 0.000 description 2
- 229960001948 caffeine Drugs 0.000 description 2
- VJEONQKOZGKCAK-UHFFFAOYSA-N caffeine Natural products CN1C(=O)N(C)C(=O)C2=C1C=CN2C VJEONQKOZGKCAK-UHFFFAOYSA-N 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
- 239000004310 lactic acid Substances 0.000 description 2
- 235000014655 lactic acid Nutrition 0.000 description 2
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 208000004880 Polyuria Diseases 0.000 description 1
- ABBQHOQBGMUPJH-UHFFFAOYSA-M Sodium salicylate Chemical compound [Na+].OC1=CC=CC=C1C([O-])=O ABBQHOQBGMUPJH-UHFFFAOYSA-M 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- QJLYKBIVMWMIDH-UHFFFAOYSA-N [Ca].CN1C(=O)N(C)C(=O)C2=C1N=CN2C Chemical compound [Ca].CN1C(=O)N(C)C(=O)C2=C1N=CN2C QJLYKBIVMWMIDH-UHFFFAOYSA-N 0.000 description 1
- 230000003276 anti-hypertensive effect Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 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
- 159000000007 calcium salts Chemical class 0.000 description 1
- WLPACTAQECUARH-UHFFFAOYSA-L calcium;1,3-dimethyl-2-oxopurin-6-olate Chemical compound [Ca+2].CN1C(=O)N(C)C([O-])=C2N=CN=C21.CN1C(=O)N(C)C([O-])=C2N=CN=C21 WLPACTAQECUARH-UHFFFAOYSA-L 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 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
- C07D473/08—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 and 3, e.g. theophylline
-
- 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
- C07D473/10—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 3 and 7, e.g. theobromine
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung von leicht löslichen Doppelsalzen aus monomethyl-, Dimethyl- und Trimethylxanthinen. Der Verwendung der diuretisch wirkenden Basen der Coffeinreihe, insbesondere des Theobromins, stand die schwere Resorbierbarkeit und die Schwerlöslichkeit der Verbindungen im Wege. Diese Schwierigkeit wurde in Ansehung des Theobr omins und Coffeins durch die Darstellung leicht löslicher Doppelsalze mit Natriumsalicylat, wie z. B. des Theobrominnatrium - Natriumsalicylats, behoben.Process for the preparation of easily soluble double salts from monomethyl, Dimethyl and trimethyl xanthines. The use of the diuretic bases the caffeine series, especially theobromine, was due to the difficulty of absorbing it and the poor solubility of the compounds in the way. This difficulty was found in Appreciation of theobromine and caffeine through the presentation of easily soluble double salts with sodium salicylate, such as. B. of theobromine sodium - sodium salicylate.
Nach dem Verfahren der britischen Patentschrift Nr. 26838/19o6 wurde auch Milchsäure als zweite Komponente der Doppelsalze verwendet und auf diese Weise Theobrominnatrium-Natriumlactat hergestellt. Dieses Präparat weist neben größerer Löslichkeit auch eine Verstärkung der diuretischen Wirkung auf. Diese Verbindung ist aber nicht frei von unangenehmen Nebenwirkungen (vgl. Pharmazeutische Zeitung5a, 1907, S. d.9). Man hat ferner versucht, die Tatsache zu verwerten, daß Coffein und Theophyllin auch mit Erdalkalisalzen der aromatischen Carbonsäuren komplexe Verbindungen bilden, die zum Teil in der Therapie Verwendung finden können (vgl. Chemisches Zentralblatt r929, Bd. III, S. 957).Following the procedure of British patent specification No. 26838/19o6 was also used lactic acid as the second component of the double salts and this way Theobromine Sodium Lactate. This preparation shows in addition to larger Solubility also increases the diuretic effect. This connection but is not free from unpleasant side effects (cf.Pharmaceutical Gazette5a, 1907, p. D.9). Attempts have also been made to exploit the fact that caffeine and Theophylline also contains complex compounds with alkaline earth salts of aromatic carboxylic acids which can partly be used in therapy (see Chemisches Zentralblatt r929, Vol. III, p. 957).
Den Gegenstand der vorliegenden Erfindung bildet nun ein Verfahren -_zitr - Darstellung von Doppelsalzen der Calciumverbindungen von Monomethyl-, Dimethyl- und Trimethvlxanthinen mit Caloiitmlactat. Derartige Doppelsalze zeigen die verstärkte Wirkung aller drei .Komponenten, indem sie einerseits die blutdrucksenkende und diuretische Wirkung des Theobromins und der verwandten Verbindungen und gleichzeitig die styptische Wirkung der Calciumsalze besitzen, ohne wie bisher durch schwer abzubauende aromatische 'Carbonsäuren belastet zu sein, da die Milchsäure im Organismus vollständig verbrannt wird. Diese neuen Präparate haben daher einen gesteigerten therapeutischen Wert. Auch die Löslichkeitsverhältnisse dieser Doppelsalze, deren eine Komponente Calciumlactat ist, liegen besondes günstig. Gegenüber dem bekannten Theobrominnatrium-Natriumlactat zeigen die neuen Verbindungen überraschenderweise den Vorteil, daß sie dank dem Ersatz des Natriums durch Calcium keine unangenehn ien Nebenwirkungen aufweisen.The subject of the present invention now forms a method -_zitr - representation of double salts of the calcium compounds of monomethyl-, dimethyl- and trimethylxanthines with calicoitm lactate. Such double salts show the strengthened Effect of all three .components, on the one hand the antihypertensive and diuretic action of theobromine and related compounds and at the same time have the typical effect of calcium salts without, as has been the case up to now, difficult to break down aromatic 'carboxylic acids, since the lactic acid is completely in the organism is burned. These new preparations therefore have an increased therapeutic Value. Also the solubility ratios of these double salts, one of which is a component Calcium lactate is particularly beneficial. Compared to the well-known theobromine sodium-sodium lactate show the new compounds surprisingly the advantage that they thanks to the Replacement of sodium by calcium does not have any unpleasant side effects.
Beispiel. a Mol. Theobromin werden mit r Mol. reinen Calciumoxyds (Kalk aus Marmor) vermischt und mit wenig Wasser angerührt. Hierauf wird frisch umkristallisiertes, noch feuchtes milchsaures Calcium eingetragen, und zwar in einer Menge, die 2 Mol. des entwässerten Calciuinlactats auf r Mol. Theobroinincalcium entspricht. Das Gemisch wird sodann auf dein Wasserbad, allenfalls unter weiterem Zusatz von ein wenig Wasser, bis zur Lösung erhitzt und gegebenenfalls hernach von den geringen Verunreinigungen rasch abfiltriert, erstarren gelassen und im Vakuum getrocknet, bis sich das Salz (Theobromincalcium+2 Mol. Calciumlactat) leicht pulverisieren läßt. Ebenso kann auch die Doppelverbindung des Theobromincalciums mit r Mol. Calciumlactat hergestellt werden. In 'genau derselben Weise kann man z. B. zu Verbindungen des Theophyllincalciums, Paraxanthincalciums und Coffeincalciums mit 2 Mol. milchsaurem Calcium und r Mol. milchsaurem Calcium gelangen.Example. a mole of theobromine is obtained with r mole of pure calcium oxide (Lime from marble) mixed and mixed with a little water. Then it gets fresh recrystallized, still wet lactic acid calcium entered, namely in an amount that 2 moles of the dehydrated calcium lactate to r moles. Corresponds to theobroinine calcium. The mixture is then on your water bath, if necessary with further addition of a little water, heated to solution and if necessary then quickly filtered off the minor impurities and allowed to solidify and dried in vacuo until the salt (theobromine calcium + 2 mol. calcium lactate) easy to pulverize. Likewise, the double compound of theobromine calcium can also be used be made with r moles of calcium lactate. In exactly the same way one can z. B. to compounds of theophylline calcium, paraxanthine calcium and caffeine calcium with 2 mol. of lactic acid calcium and r mol. of lactic acid calcium.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT406211X | 1922-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE406211C true DE406211C (en) | 1924-11-15 |
Family
ID=3673674
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEF51241D Expired DE406211C (en) | 1922-02-03 | 1922-02-14 | Process for the preparation of easily soluble double salts from monomethyl-, dimethyl- and trimethylxanthines |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE406211C (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 |
-
1922
- 1922-02-14 DE DEF51241D patent/DE406211C/en not_active Expired
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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