DE221483C - - Google Patents
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- Publication number
- DE221483C DE221483C DENDAT221483D DE221483DA DE221483C DE 221483 C DE221483 C DE 221483C DE NDAT221483 D DENDAT221483 D DE NDAT221483D DE 221483D A DE221483D A DE 221483DA DE 221483 C DE221483 C DE 221483C
- Authority
- DE
- Germany
- Prior art keywords
- anhydrides
- mercury
- sulfur
- salts
- oxymercury
- 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.)
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- 150000008064 anhydrides Chemical class 0.000 claims description 10
- 239000000243 solution Substances 0.000 claims description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000001735 carboxylic acids Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- -1 alkali metal salts Chemical class 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- 125000004436 sodium atom Chemical group 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000007795 chemical reaction product Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 150000003839 salts Chemical class 0.000 description 8
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 7
- 229910052753 mercury Inorganic materials 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 230000002084 anti-luetic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WLPQCHKXJRHZRI-UHFFFAOYSA-N (2-hydroxybenzoyl) 2-hydroxybenzoate Chemical compound OC1=CC=CC=C1C(=O)OC(=O)C1=CC=CC=C1O WLPQCHKXJRHZRI-UHFFFAOYSA-N 0.000 description 1
- NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
- 239000004133 Sodium thiosulphate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- LFEZBRCLZFHLLA-UHFFFAOYSA-N [K].[Hg] Chemical compound [K].[Hg] LFEZBRCLZFHLLA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GRWZHXKQBITJKP-UHFFFAOYSA-L dithionite(2-) Chemical compound [O-]S(=O)S([O-])=O GRWZHXKQBITJKP-UHFFFAOYSA-L 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 230000035876 healing Effects 0.000 description 1
- 230000007794 irritation Effects 0.000 description 1
- 230000007721 medicinal effect Effects 0.000 description 1
- 150000002730 mercury Chemical class 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003254 radicals Chemical group 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-N sulfurothioic S-acid Chemical compound OS(O)(=O)=S DHCDFWKWKRSZHF-UHFFFAOYSA-N 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/10—Mercury compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVl 221483 -" KLASSE 12 o. GRUPPE - JVl 221483 - " CLASS 12 or GROUP
von Oxyquecksilbercarbonsäuren.of oxymercuric carboxylic acids.
Patentiert im Deutschen Reiche vom 25. Februar 1909 ab.Patented in the German Empire on February 25, 1909.
Obwohl die anorganische und organische Synthese der Luestherapie eine außerordentlich große Reihe von Quecksilberpräparaten geliefert hat, ist die Zahl derjenigen Stoffe, welche für die Lösung des Problems in Frage kommen, eine außerordentlich kleine, eine Tatsache, die in der Schwierigkeit der Aufgabe begründet ist. Man verlangt heute mit Recht, daß ein Antiluetikum neutral wasserlöslich, reizlos bzw. schmerzfrei injizierbar ist und ferner das Quecksilber so larviert enthält, daß es langsam und gleichmäßig zur Wirkung kommen kann. Diesen außerordentlich hohen Anforderungen gegenüber kommen heute nur die folgenden Präparate in Betracht : einmal die Alkalisalze der Quecksilberphenolsulfosäurenx) und ebenso die der Quecksilberdipropionsäure2), in all denen jedoch das Quecksilber wohl auf Grund der chemischen Konstitution dieser Verbindungen seine Heilwirkung verloren hat, sodann die Quecksilbereiweißverbindungen, die infolge ihres geringen Metallgehaltes (7 Prozent) wenig praktische Bedeutung besitzen, und zuletzt das von Dreser empfohlene quecksilber unterschwefligsaure Kalium, das jedoch hauptsächlich infolge seiner Zersetzlichkeit keine Verbreitung finden konnte.Although the inorganic and organic synthesis of pleasure therapy has produced an extraordinarily large series of mercury preparations, the number of those substances which can be used to solve the problem is an extremely small one, a fact which is based on the difficulty of the task. Nowadays it is rightly demanded that an antiluetic agent is neutral water-soluble, can be injected without irritation or painlessly and furthermore contains the mercury in such a way that it can take effect slowly and evenly. In relation to these extraordinarily high requirements, only the following preparations come into consideration today: firstly the alkali salts of mercury phenol sulfonic acids x ) and also those of mercury dipropionic acid 2 ), in all of which, however, the mercury has lost its medicinal properties due to the chemical constitution of these compounds, then the Mercury protein compounds, which are of little practical importance due to their low metal content (7 percent), and finally the hyposulphurous mercury potassium recommended by Dreser, which, however, was not widely used mainly due to its decomposition.
Die vorliegende Erfindung ist nun von der Tatsache ausgegangen, daß die beste Heil-The present invention is based on the fact that the best healing
*) D. R. P. 132660, Kl. 12.*) D. R. P. 132660, class 12.
2) Ber. d. deutsch, ehem. Ges. 40, 386 (1907). 2 ) Ber. d. German, former Ges. 40, 386 (1907).
wirkung heute immer noch erzielt wird mit den in Wasser unlöslichen Anhydriden der Oxyquecksilbercarbonsäuren, zu denen auch das meistverwandte Hydrargyrum salicylicum des Arzneibuches gehört. Diesen Präparaten fehlt zu einem idealen Antiluetikum lediglich die Wasserlöslichkeit, die mit Alkalien zwar zu erzielen ist, aber auf diesem Wege nicht zu neutral reagierenden Lösungen führt.effect is still achieved today with the anhydrides which are insoluble in water Oxymercury carboxylic acids, which also include the most closely related Hydrargyrum salicylicum of the Pharmacopoeia. These preparations are simply missing for an ideal antiluetic the water solubility, which can be achieved with alkalis, but not in this way leads to neutral reacting solutions.
Diese letzte Schwierigkeit hat nun die vorliegende Erfindung durch die Beobachtung beseitigt, daß solche Anhydride mit großer Heftigkeit unter Aufspaltung der Anhydridbindung mit den wässerigen Lösungen eines Moleküls solcher Salze reagieren, die mindestens ein Natriumatom an Schwefel gebunden enthalten, derart, daß dieses Natriumatom an das Karboxyl wandert und das Quecksilber sich mit dem Schwefelrest bindet nach der allgemeinen Gleichung:This last difficulty has now been overcome by the present invention by observing that such anhydrides act with great violence with splitting of the anhydride bond react with the aqueous solutions of a molecule of such salts that at least contain a sodium atom bonded to sulfur, such that this sodium atom to the carboxyl migrates and the mercury binds with the sulfur residue after the general equation:
HgACOO + XSNa = XSHgACOONa, in der A irgendeinen Alkyl- oder Arylrest und X ein an Schwefel gebundenes Radikal bedeutet. Während man es bei der Lösung der Anhydride in z. B. Halogenalkalien, phosphorsauren Salzen u. a., die nur bei Anwendung von mehr als einem Molekül dieser Salze möglich ist, wahrscheinlichst mit einer mechanischen Lösung zu tun hat, die vielfach zur Bildung von Doppelsalzen führt, tritt bei Anwendung der vorerwähnten schwefelhaltigen Salze eine chemische Reaktion ein, die sich HgACOO + XSNa = XSHgACOONa, in which A is any alkyl or aryl radical and X is a radical bonded to sulfur. While it is the solution of the anhydrides in z. B. halogenated alkalis, phosphoric acid salts, etc., which is only possible when using more than one molecule of these salts, most likely has to do with a mechanical solution that often leads to the formation of double salts, a chemical reaction occurs when using the aforementioned sulfur-containing salts , which
meist unter lebhafter Wärmeentwicklung vollzieht. Solche Salze sind neben anderen das Alkalisulfit, -thiosulfat, -hydrosulfit, die Alkalisalze der geschwefelten Alkohole und Phenole und die thiosulfonsauren Salze.usually takes place with vigorous heat development. Such salts are among others that Alkali sulfite, thiosulfate, hydrosulfite, the alkali salts of sulphurized alcohols and Phenols and the thiosulphonic acid salts.
Ausführungsbeispiele.Embodiments.
i. io g Natriumthiosulfat werden in 30 ecm Wasser gelöst und in die gekühlte Lösungi. 10 g of sodium thiosulphate are in 30 ecm Dissolve water and add to the cooled solution
ίο allmählich 16,5 g Oxyquecksilberessigsäureanhydrid eingetragen (Theorie 16,33 g)· Das Anhydrid geht unter Wärmeentwicklung in Lösung; von dem geringen Anhydridrückstand wird abfiltriert und die gelblich gefärbte Lösung im-Vakuum bei tiefer Temperatur eingedampft. Der zähe Rückstand wird beim Anreiben mit Aceton, Methylalkohol und anderen wasserentziehenden Mitteln fest und pulverförmig. In Wasser ist er mit neutraler Reaktion spielend löslich, sein Quecksilbergehalt beträgt entsprechend der Formel:ίο gradually 16.5 g of oxymercury acetic anhydride registered (theory 16.33 g) · The anhydride goes into solution with development of heat; the small anhydride residue is filtered off and the yellowish colored solution evaporated in vacuo at low temperature. The tough residue is when Rub with acetone, methyl alcohol and other dehydrating agents firmly and powdery. Its mercury content is easily soluble in water with a neutral reaction is according to the formula:
-S-HgCH2-COONa-S-HgCH 2 -COONa
48,07 Prozent.48.07 percent.
Analoge Derivate erhält man in ähnlicher Weise auch durch die Kombination der andern oben genannten schwefelhaltigen Salze mit Oxyquecksilberessigsäureanhydrid bzw. mit den Anhydriden anderer Oxyquecksilberfettsäuren. Analogous derivatives are obtained in a similar way by combining the others above-mentioned sulfur-containing salts with oxymercuric acid anhydride or with the anhydrides of other oxymercury fatty acids.
2. 10 g Natriumsulfit werden in 30 ecm Wasser gelöst und in die gekühlte Lösung2. 10 g of sodium sulfite are in 30 ecm Dissolve water and add to the cooled solution
allmählich 25,5 g Oxyquecksilberbenzoesäureanhydrid eingetragen (Theorie 25,39); die er' haltene Lösung wird wie oben beschrieben weiter behandelt. Das erhaltene Produkt besitzt entsprechend der Formel:gradually added 25.5 g of oxymercury benzoic anhydride (theory 25.39); he 'preserved solution is further treated as described above. The product obtained has according to the formula:
HgC6H^COONaHgC 6 H ^ COONa
= °= °
-ONa-ONa
einen Quecksilbergehalt von 44,84 Prozent.a mercury content of 44.84 percent.
Analoge Derivate erhält man durch Kombination auch der übrigen diesbezüglichen schwefelhaltigen Salze mit diesem Anhydrid bzw. mit den Anhydriden der übrigen aromatischen Oxyquecksilbercarbonsäuren, wie z. B. Oxyquecksilbersalicylsäureanhydrid usw.Analogous derivatives are also obtained by combining the other relevant derivatives sulfur-containing salts with this anhydride or with the anhydrides of the other aromatic ones Oxymercuric carboxylic acids, such as. B. Oxymercury salicylic anhydride, etc.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE221483C true DE221483C (en) |
Family
ID=482451
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT221483D Active DE221483C (en) |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE221483C (en) |
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