DE208188C - - Google Patents
Info
- Publication number
- DE208188C DE208188C DE1907208188D DE208188DA DE208188C DE 208188 C DE208188 C DE 208188C DE 1907208188 D DE1907208188 D DE 1907208188D DE 208188D A DE208188D A DE 208188DA DE 208188 C DE208188 C DE 208188C
- Authority
- DE
- Germany
- Prior art keywords
- theobromine
- sodium
- salts
- caffeine
- iodine
- 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 - Lifetime
Links
- 239000011780 sodium chloride Substances 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- 239000003513 alkali Substances 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- YAPQBXQYLJRXSA-UHFFFAOYSA-N Theobromine Chemical class CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 description 32
- 229960004559 Theobromine Drugs 0.000 description 16
- RYYVLZVUVIJVGH-UHFFFAOYSA-N caffeine Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2C RYYVLZVUVIJVGH-UHFFFAOYSA-N 0.000 description 12
- -1 Theobromine Sodium - Chlorine Sodium Chemical compound 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M Sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 229960001948 caffeine Drugs 0.000 description 6
- ZIQRIAYNHAKDDU-UHFFFAOYSA-N sodium;hydroiodide Chemical compound [Na].I ZIQRIAYNHAKDDU-UHFFFAOYSA-N 0.000 description 5
- IOLCXVTUBQKXJR-UHFFFAOYSA-M Potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-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 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229960004025 sodium salicylate Drugs 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N Benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 229940083599 Sodium Iodide Drugs 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M Sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000000875 corresponding Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000000926 separation method Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 230000001225 therapeutic Effects 0.000 description 2
- XXSSHQCOBPQFOL-UHFFFAOYSA-N 1,3,7-trimethylpurine-2,6-dione;hydrobromide Chemical compound [Br-].O=C1N(C)C(=O)N(C)C2=C1[NH+](C)C=N2 XXSSHQCOBPQFOL-UHFFFAOYSA-N 0.000 description 1
- REWPEPFZCALMJB-UHFFFAOYSA-N 2-hydroxybenzoic acid;sodium Chemical compound [Na].OC(=O)C1=CC=CC=C1O REWPEPFZCALMJB-UHFFFAOYSA-N 0.000 description 1
- CORZNQNMOFOBGZ-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione;potassium Chemical class [K].CN1C(=O)NC(=O)C2=C1N=CN2C CORZNQNMOFOBGZ-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- NLKNQRATVPKPDG-UHFFFAOYSA-M Potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive Effects 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium(0) Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- PEDCQBHIVMGVHV-UHFFFAOYSA-N glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 229940075581 sodium bromide Drugs 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 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
- C07D473/10—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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- M 208188 — KLASSE Mp. GRUPPE- M 208188 - CLASS GROUP Mp.
in FRANKFURT a. M.in FRANKFURT a. M.
Die Herstellung von Doppelsalzen des Theobromins, welche leichter in Wasser löslich sind als das freie Theobromin, geschah bisher meist in der Weise, daß man Theobrominnatrium mit molekularen Mengen von Alkalisalzen organischer Säuren vereinigte. Man hat auf diese Weise Doppelsalze mit ameisensaurem, essigsaurem, milchsaurem, benzoesaurem, salicylsaurem Natrium oder Lithium gewonnen.The production of double salts of theobromine, which are more easily soluble in water as the free theobromine, has hitherto usually been done in such a way that theobromine sodium is used combined with molecular quantities of alkali salts of organic acids. One has on In this way, double salts with formic acid, acetic acid, lactic acid, benzoic acid, salicylic acid Sodium or lithium extracted.
ίο Es wurde nun gefunden, daß sich therapeutisch wertvolle Theobromindoppelsalze durch Vereinigung molekularer Mengen Theobrominnatrium mit Halogenalkalien darstellen lassen, so z. B. Theobrominnatrium - Chlornatrium, Theobrominnatrium-Bromnatrium,Theobromin natrium-Jodnatrium. Diese Verbindungen besitzen alle den Vorzug leichter Löslichkeit in Wasser. Das Chlornatriumdoppelsalz zeichnet sich zudem durch einen sehr hohen Theobromingehalt aus, wie er keinem andern ähnlichen Präparat zukommt, und es besitzt ferner den Vorzug, daß das Theobromin ohne Zusatz einer dem Organismus fremden Säure zur Wirkung kommen kann. Andere Salze, z. B.ίο It has now been found to be therapeutic valuable theobromine double salts by combining molecular quantities of theobromine sodium let represent with haloalkali, so z. B. Theobromine Sodium - Chlorine Sodium, Sodium theobromine-bromine, sodium theobromine-iodine. These compounds all have the advantage of being readily soluble in water. The chlorosodium double salt draws is also characterized by a very high theobromine content, unlike any other Preparation, and it also has the advantage that theobromine without any additive an acid foreign to the organism can take effect. Other salts, e.g. B.
das Bromriatrium- und Jodnatriumdoppelsalz, enthalten neben Theobromin andere therapeutisch wirksame Komponenten, welche in dieser Verbindung oft besonders zweckmäßig wirken. Aus Hagers Handbuch der Pharmazeutisehen Praxis, Neue Bearbeitung, Bd. II, 1902, S. 1045, ist em Gemenge von Theobromin, Jodnatrium und Natriumsalicylat bekannt geworden, das therapeutische Verwendung ge- the sodium bromide and sodium iodine salt contain, in addition to theobromine, other therapeutically effective components which are often particularly effective in this connection. From Hager's Handbook of Pharmazeutisehen practice, new processing, Vol. II, 1902, p 1045, em mixture of theobromine, sodium iodide and sodium salicylate has been known overall therapeutic use
■ funden haben soll; dieses Jodotheobromin ist aber mit den nach den vorliegenden Verfahren hergestellten Produkten nicht zu vergleichen. Es ist lediglich ein Gemenge von Theobromin, Jodnatrium und Natriumsalicylat, und seine einzelnen Bestandteile sind nicht in molekularen Verhältnissen, sondern in beliebiger Weise gemischt. In den Präparaten des vorliegenden Verfahrens ist keine Spur von Natriumsalicylat enthalten, das einen unerläßlichen Bestandteil des Rezeptes . nach Hager bildet und dort zur Vergrößerung der Löslichkeit des Theobromins beigefügt wurde. Nach dem vorliegenden Verfahren wird dagegen die erhöhte Löslichkeit des Theobromins durch Vereinigung seines Natriumsalzes mit Halogenalkalien bewirkt. , ■ should have found; however, this iodotheobromine cannot be compared with the products produced by the present process. It is just a mixture of theobromine, sodium iodine and sodium salicylate, and its individual components are not in molecular proportions, but mixed in any way. No trace of sodium salicylate, which is an indispensable part of the recipe, is contained in the preparations of the present process. according to Hager and was added there to increase the solubility of theobromine. According to the present process, however, the increased solubility of theobromine is brought about by combining its sodium salt with halogenated alkalis. ,
Ferner sind sogenannte Doppel verbindungen aus Coffein und Halogenalkalien, z. B. das Coffeino-Kaliumbromid und Natriumiodid bekannt (vgl. Hagers Handbuch der Pharmazeutischen Praxis, Neue Bearbeitung, Bd. I [1900], S. 913), diese sind aber lediglich Gemenge von willkürlicher Zusammensetzung. Das Coffeino-Kaliumbromid besteht aus gleichen Teilen Coffein und Bromkalium, das Coffeino-Natriumjodid 'aus 7,1 Teilen Coffein und 2,9 Teilen Jodnatrium, es liegen also nicht einmal Gemenge in molekularen Verhältnissen vor. Sie können deshalb mit den nach dem vorliegenden Verfahren gewonnenen Präparaten in keiner Weise verglichen werden. Außerdem zeigt das Coffein wesentlich abweichende Reaktionen vom Theobromin. Dieses ist in Alkalien löslich und verbindet sich mit ihnen sowie mitFurthermore, so-called double compounds of caffeine and halogenated alkalis, z. B. that Caffeine potassium bromide and sodium iodide known (cf. Hagers Handbuch der Pharmazeutischen Praxis, New Editing, Vol. I [1900], P. 913), but these are merely a mixture of arbitrary composition. The caffeine potassium bromide consists of equal parts of caffeine and potassium bromide, the caffeinosodium iodide consists of 7.1 parts of caffeine and 2.9 parts Sodium iodine, so there are not even mixtures in molecular proportions. she can therefore not be used in any of the preparations obtained by the present process Way to be compared. In addition, the caffeine shows significantly different reactions from theobromine. This is soluble in alkalis and combines with them as well as with
Barium zu gut charakterisierten Salzen (vgl. Beilstein, 3. Aufl., Bd. Ill, S. 955), während Coffein nicht allein nicht löslich in Basen ist, sondern beim Kochen damit verändert wird. Da die nach dem vorliegenden Verfahren darzustellenden Produkte Verbindungen von Halogenalkalien mit den oben erwähnten Alkalisalzen des Theobromins sind, so sind sie ganz verschieden von obigen Gemengen aus Coffein und Halogenalkalien, was sich schon aus dem analytischen Verhalten der neuen Doppelsalze ergibt. Sie werden nämlich durch Säuren unter Abscheidung von Theobromin zersetzt.Barium to well-characterized salts (cf. Beilstein, 3rd ed., Vol. Ill, p. 955), while Caffeine is not by itself not soluble in bases, but is changed with it during cooking. Since the products to be prepared according to the present process are compounds of halo-alkalis with the above-mentioned alkali salts of theobromine, they are whole different from the above blends of caffeine and halo-alkalis, which can already be seen from the analytical behavior of the new double salts results. This is because they are decomposed by acids with the separation of theobromine.
Vor jenen willkürlich zusammengesetzten Coffeindoppelverbindungen haben also die nach
' vorliegendem Verfahren hergestellten Produkte den Vorzug, eine bestimmte molekulare Zusammensetzung
zu besitzen, was für den Arzt von besonderem Wert ist. Auch wirken sie physiologisch wesentlich anders, und der Arzt
kann keineswegs ohne weiteres das eine Präparat für das andere verschreiben.
, Das Jodnatriumdoppelsalz enthält die wirksamen Bestandteile Jodnatrium und Theobromin
in annähernd gleichen Mengen, und es hat sich bei klinischer Prüfung als ein sehr
günstig bei gewissen Krankheiten wirkendes Präparat erwiesen.Over those arbitrarily composed caffeine double compounds, the products manufactured according to the present process have the advantage of having a specific molecular composition, which is of particular value to the doctor. Physiologically, they also have a significantly different effect, and the doctor cannot simply prescribe one preparation for the other.
The sodium iodine double salt contains the active ingredients sodium iodine and theobromine in approximately equal amounts, and clinical tests have shown it to be a very beneficial preparation for certain diseases.
18,0 Teile Theobromin werden mittels einer mäßig koncentrierten Lösung von 4 Teilen Ätznatron in Wasser gelöst und 5,85 Teile reines Chlornatrium zugefügt. Die Lösung wird, falls nötig, filtriert, eingedampft und der Rückstand getrocknet und zerrieben.18.0 parts of theobromine are obtained using a moderately concentrated solution of 4 parts of caustic soda dissolved in water and added 5.85 parts of pure sodium chloride. The solution is if necessary, filtered, evaporated and the residue dried and triturated.
20,2 Teile in bekannter Weise hergestelltes trockenes Theobrominnatrium werden zusammen mit 15 Teilen Jodnatrium in möglichst wenig Wasser gelöst, die Lösung zur Trockne gebracht und der Rückstand gepulvert.20.2 parts of dry theobromine sodium produced in a known manner are combined dissolved with 15 parts of sodium iodine in as little water as possible, the solution to dryness brought and the residue powdered.
Selbstverständlich kann man diese Darstellungsart noch in mancher Weise abändern, auch lassen sich an Stelle der Halogennatriumsalze die entsprechenden Salze anderer Alkalien, z. B. Jodkalium oder Bromkalium, mit den Theobrominalkaliverbindungen kombinieren.Of course, you can still change this type of representation in some ways, Instead of the sodium halide salts, the corresponding salts of other alkalis, z. B. potassium iodine or potassium bromide, combine with the theobromine potassium compounds.
Die Theobromin-Halogenalkalidoppelsalze bilden sämtlich weiße, alkalisch reagierende, bitter schmeckende Pulver, sie sind leicht löslich in Wasser und verdünnten Alkalien, werden aber durch Säuren unter Abscheidung von Theobromin zersetzt. Durch die üblichen Reagenzien läßt sich in ihnen das Halogen, Jod, Brom oder Chlor leicht nachweisen, ebenso durch entsprechende Reaktionen der Kaliumoder Natriumgehalt. Alle Salze sind unlöslich in Äther, Petroläther und Benzol, in äbsolutem Alkohol lösen sie sich auch beim Kochen sehr schwer, während · sie in verdünntem Alkohol und Glycerin, besonders beim Erwärmen, leicht löslich sind.The theobromine haloalkali double salts all form white, alkaline reacting, bitter-tasting powders, they are easily soluble in water and dilute alkalis but decomposed by acids with the separation of theobromine. The halogen, Easily detect iodine, bromine or chlorine, also by corresponding reactions of the potassium or Sodium content. All salts are insoluble in ether, petroleum ether and benzene, in absolute Alcohol they dissolve very difficult also when boiling, while · they dissolve in diluted alcohol and glycerin, especially when heated, are readily soluble.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AT39611D AT39611B (en) | 1907-05-30 | 1909-03-13 | Process for the preparation of easily soluble double salts from theobromine sodium and alkali halides. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE208188C true DE208188C (en) |
Family
ID=470241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1907208188D Expired - Lifetime DE208188C (en) | 1907-05-30 | 1907-05-30 |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE208188C (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102017216389A1 (en) * | 2017-09-15 | 2019-03-21 | Thyssenkrupp Ag | Mobile conveyor bridge system with decoupled settling system |
-
1907
- 1907-05-30 DE DE1907208188D patent/DE208188C/de not_active Expired - Lifetime
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102017216389A1 (en) * | 2017-09-15 | 2019-03-21 | Thyssenkrupp Ag | Mobile conveyor bridge system with decoupled settling system |
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