DE262328C - - Google Patents
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- Publication number
- DE262328C DE262328C DENDAT262328D DE262328DA DE262328C DE 262328 C DE262328 C DE 262328C DE NDAT262328 D DENDAT262328 D DE NDAT262328D DE 262328D A DE262328D A DE 262328DA DE 262328 C DE262328 C DE 262328C
- Authority
- DE
- Germany
- Prior art keywords
- acid
- salicylic acid
- water
- compound
- salicylic
- 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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- YGSDEFSMJLZEOE-UHFFFAOYSA-N Salicylic acid Natural products OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims description 24
- BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 18
- 229960004889 salicylic acid Drugs 0.000 claims description 13
- 235000019253 formic acid Nutrition 0.000 claims description 6
- KGBXLFKZBHKPEV-UHFFFAOYSA-N Boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 claims description 4
- 239000004327 boric acid Substances 0.000 claims description 4
- 239000003513 alkali Substances 0.000 claims description 3
- -1 salicylic acid compound Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 230000002421 anti-septic Effects 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 231100000486 side effect Toxicity 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N Carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 2
- 210000004400 Mucous Membrane Anatomy 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M NaHCO3 Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 2
- 201000009240 nasopharyngitis Diseases 0.000 description 2
- 239000001187 sodium carbonate Substances 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- 210000004369 Blood Anatomy 0.000 description 1
- 230000036826 Excretion Effects 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
- 238000004458 analytical method Methods 0.000 description 1
- 235000019658 bitter taste Nutrition 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000002308 calcification Effects 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- LVSJLTMNAQBTPE-UHFFFAOYSA-N disodium tetraborate Chemical compound [Na+].[Na+].O1B(O)O[B-]2(O)OB(O)O[B-]1(O)O2 LVSJLTMNAQBTPE-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 230000029142 excretion Effects 0.000 description 1
- 230000002458 infectious Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- WVYADZUPLLSGPU-UHFFFAOYSA-N salsalate Chemical compound OC(=O)C1=CC=CC=C1OC(=O)C1=CC=CC=C1O WVYADZUPLLSGPU-UHFFFAOYSA-N 0.000 description 1
- 229960000953 salsalate Drugs 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000035943 smell Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229960004025 sodium salicylate Drugs 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000004328 sodium tetraborate Substances 0.000 description 1
- 235000010339 sodium tetraborate Nutrition 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/60—Salicylic acid; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/01—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups
- C07C65/03—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring
- C07C65/05—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing hydroxy or O-metal groups monocyclic and having all hydroxy or O-metal groups bound to the ring o-Hydroxy carboxylic acids
- C07C65/10—Salicylic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
-JVe 262328-KLASSE 12 q. GRUPPE-JVe 262328-CLASS 12 q. GROUP
HANS WEITZ in BERLIN-WILMERSDORF.HANS WEITZ in BERLIN-WILMERSDORF.
Verfahren zur Herstellung einer Salicylsäureverbindung.Method for producing a salicylic acid compound.
Patentiert im Deutschen Reiche vom 25. Mai 1912 ab.Patented in the German Empire on May 25, 1912.
Das vorliegende Verfahren betrifft die Herstellung einer Salicylsäureverbindung, welche schnell und klar in Wasser löslich ist, die unangenehmen Nebenwirkungen der Salicylsäure und ihres Natriumsalzes nicht aufweist, sich viele Tage ohne Ausscheidung im Blute hält und sich durch eine kräftigere antiseptische Wirkung auszeichnet.The present method relates to the production of a salicylic acid compound which is quickly and clearly soluble in water, the unpleasant side effects of salicylic acid and its sodium salt does not show up for many days without excretion in the blood lasts and is characterized by a stronger antiseptic effect.
Dieser technische Fortschritt wird dadurch ίο erreicht, daß man Salicylsäure und Borsäure mit Ameisensäure bei Gegenwart von Alkali kondensiert.This technical progress is achieved by using salicylic acid and boric acid condensed with formic acid in the presence of alkali.
744 g Borsäure werden mit 138 g Salicylsäure und 1144 g Soda verrieben. Anstatt Natriumcarbonat kann die äquivalente Menge Natronlauge oder Natriumbicarbonat genommen werden. Das Gemisch wird in möglichst wenig744 g of boric acid are triturated with 138 g of salicylic acid and 1144 g of soda. Instead of Sodium carbonate can be the equivalent amount of caustic soda or sodium bicarbonate taken will. The mixture is in as little as possible
ao Wasser bei einer Temperatur von 140 ° zur Lösung gebracht und so lange erhitzt, bis die Lösung eine gelbliche Farbe angenommen hat. Alsdann setzt man 46 g Ameisensäure hinzu und hält das Ganze so lange bei 60°, bis die Kohlensäure verjagt ist. Darauf säuert man die Lösung so weit mit Ameisensäure an, bis eine schwach bläulichviolette Färbung entsteht. Hierauf setzt man das Ganze zur Kristallisation an einen kühlen Ort.ao water brought to the solution at a temperature of 140 ° and heated until the Solution has turned a yellowish color. Then 46 g of formic acid are added and keep the whole thing at 60 ° until the carbonic acid is gone. You get sour on it add formic acid to the solution until it turns a pale bluish-violet color. Then you put the whole thing in a cool place to crystallize.
Der sich ausscheidende Körper ist in kaltem Wasser schwer, in heißem Wasser leicht löslich, in Äthylalkohol schwer, in Aceton sehr schwer löslich, in Äther und Ligroin unlöslich, sehr leicht löslich dagegen in Methylalkohol. Der Schmelzpunkt des Körpers wurde auch nach wiederholtem Umkristallisieren zu 106 bis 107° C. gefunden. Die Analyse der Verbindung ergab: 13,90 Prozent Na, 9,72 Prozent B, 7,03 Prozent C und 4,31 Prozent H. Beim Erhitzen verliert der Körper Wasser und Ameisensäure, bei stärkerem Erhitzen tritt Geruch nach Phenol auf. Unwesentlich ist, in welcher Form das Alkali angewendet wird. Man erhält z. B. denselben Körper, wenn man eine äquivalente Menge Natriumtetraborat und eine entsprechend geringere Menge Natriumcarbonat benutzt.The excreted body is difficult to dissolve in cold water, easily soluble in hot water, poorly in ethyl alcohol, very poorly soluble in acetone, insoluble in ether and ligroin, but very easily soluble in methyl alcohol. The melting point of the body was found to be 106 to 107 ° C. even after repeated recrystallization. The analysis of the compound showed: 13.90 percent Na, 9.72 percent B, 7.03 percent C and 4.31 percent H. When heated, the body loses water and formic acid; when heated more strongly, it smells of phenol. It is immaterial in which form the alkali is used. One obtains z. B. the same body if you use an equivalent amount of sodium tetraborate and a correspondingly smaller amount of sodium carbonate.
Die neue chemische Doppelverbindung hat sich besonders wirksam als Mittel zur Abtötung der das seuchenhafte Verkalben der Kühe hervorrufenden Bakterien bewährt, da sie die bekannten schädlichen Nebenwirkungen der Salicylsäure und des Natriumsalicylats nicht zeigt und ihre Wirkung erheblich länger andauert. Auch als äußerliches Mittel bei der Bekämpfung des infektiösen Scheidenkatarrhs der Kühe ist sie der' Salicylsäure an antiseptischer Wirkung überlegen, ohne die ätzende Wirkung der Salicylsäure auf die Schleimhäute zu besitzen. Sie wird infolge ihrer leichten Löslichkeit in warmem Wasser bei Scheidenkatarrh von den ausgeschiedenen Sekreten leicht aufgelöst und dringt durch die Poren der Schleimhäute ohne Reizwirkung ein, vermag also auch auf die tief in ihnen festsitzenden Streptokokken eine antiseptische Wirkung auszuüben.The new chemical double compound has proven particularly effective as a means of killing the bacteria causing the disease-like calcification of the cows, there they the known harmful side effects of salicylic acid and sodium salicylate does not show and its effect lasts considerably longer. Also as an external means to combat the infectious vaginal catarrh of the cows it is the 'salicylic acid superior antiseptic effect without the caustic effect of salicylic acid on the Own mucous membranes. It is due to its easy solubility in warm water in vaginal catarrh easily dissolved by the secretions excreted and penetrated the pores of the mucous membranes without irritation, so it can also affect those deep within them stuck streptococci exert an antiseptic effect.
Mit Bordisalicylsäure und deren Salzen lassen sich die angeführten therapeutischen Wirkungen nicht erzielen. Bordisalicylsäure ist in freiem Zustande nicht beständig und das unter diesem Namen bekannte mecha-With Bordisalicylic acid and its salts, the listed therapeutic Not achieving effects. Bordisalicylic acid is not stable in the free state and the mechanism known under this name
nische Gemenge von Borsäure und Salicylsäure (vgl. Mercks Index 3. Aufl. 1910, S. 5; • Hagers Handbuch der Pharm. Praxis. Neue Bearb. Bd. I [1905], S. 102) zeigt natürlich alle bekannten Mängel der freien Salicylsäure. Die bekannten, bitter schmeckenden Salze der Bordisalicylsäure (vgl. Archiv der Pharmazie 212 [1878], S. 212 bis 226) werden schon durch kaltes Wasser zersetzt, so daß sich bei einigem Stehen freie Salicylsäure ausscheidet, wodurch wiederum die unangenehmen Nebenwirkungen der Salicylsäure eintreten. Die Salze haben deshalb in der Praxis keine weitere Anwendung gefunden. Die neue Verbindung hat dagegen nicht den bitteren Geschmack dieser Salze und löst sich schon in kaltem Wasser auf, ohne der Zersetzung zu unterliegen, zumal sie ja bereits eine erhebliche Menge Kristallwasser enthält.niche mixtures of boric acid and salicylic acid (cf. Mercks Index 3rd edition 1910, p. 5; • Hager's Handbook of Pharmaceutical Practice. New Ed. Vol. I [1905], p. 102) shows, of course all known deficiencies in free salicylic acid. The well-known, bitter-tasting salts of the Bordisalicylic acid (cf. Archiv der Pharmazie 212 [1878], pp. 212 to 226) are already decomposed by cold water, so that free salicylic acid is excreted when standing for a while, which in turn causes the unpleasant side effects of salicylic acid. the Salts have therefore not found any further application in practice. The new connection on the other hand does not have the bitter taste of these salts and dissolves in cold water without being subject to decomposition, especially since it is already a considerable one Contains amount of crystal water.
Über die chemische Zusammensetzung der neuen Verbindung lassen sich bestimmte Angaben nicht machen. Wahrscheinlich enthält die Doppelverbindung die Ameisensäure esterartig an den Salicylsäurerest gebunden.Certain information can be obtained about the chemical composition of the new compound not do. The double compound probably contains formic acid like an ester bound to the salicylic acid residue.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE262328C true DE262328C (en) |
Family
ID=519796
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT262328D Active DE262328C (en) |
Country Status (1)
| Country | Link |
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| DE (1) | DE262328C (en) |
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