DE187869C - - Google Patents
Info
- Publication number
- DE187869C DE187869C DENDAT187869D DE187869DA DE187869C DE 187869 C DE187869 C DE 187869C DE NDAT187869 D DENDAT187869 D DE NDAT187869D DE 187869D A DE187869D A DE 187869DA DE 187869 C DE187869 C DE 187869C
- Authority
- DE
- Germany
- Prior art keywords
- oxyquinoline
- salt
- sulfonic acid
- water
- acid
- 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
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- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 8
- 238000002844 melting Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000000843 powder Substances 0.000 description 7
- 229960003540 oxyquinoline Drugs 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 5
- ZREIPSZUJIFJNP-UHFFFAOYSA-K Bismuth subsalicylate Chemical compound C1=CC=C2O[Bi](O)OC(=O)C2=C1 ZREIPSZUJIFJNP-UHFFFAOYSA-K 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- SQGYOTSLMSWVJD-UHFFFAOYSA-N Silver nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- GGCZERPQGJTIQP-UHFFFAOYSA-M Sodium 2-anthraquinonesulfonate Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)[O-])=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-M 0.000 description 2
- 159000000009 barium salts Chemical class 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 230000000249 desinfective Effects 0.000 description 2
- 230000000968 intestinal Effects 0.000 description 2
- 159000000001 potassium salts Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- MCJGNVYPOGVAJF-UHFFFAOYSA-N 8-Hydroxyquinoline Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- LGDFHDKSYGVKDC-UHFFFAOYSA-N 8-hydroxyquinoline-5-sulfonic acid Chemical compound C1=CN=C2C(O)=CC=C(S(O)(=O)=O)C2=C1 LGDFHDKSYGVKDC-UHFFFAOYSA-N 0.000 description 1
- -1 B. the sodium salt Chemical class 0.000 description 1
- 229940049676 BISMUTH HYDROXIDE Drugs 0.000 description 1
- 235000005979 Citrus limon Nutrition 0.000 description 1
- 240000002268 Citrus limon Species 0.000 description 1
- 206010016256 Fatigue Diseases 0.000 description 1
- 210000003491 Skin Anatomy 0.000 description 1
- 210000003932 Urinary Bladder Anatomy 0.000 description 1
- 210000001635 Urinary Tract Anatomy 0.000 description 1
- DJWUNCQRNNEAKC-UHFFFAOYSA-L Zinc acetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O DJWUNCQRNNEAKC-UHFFFAOYSA-L 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000001476 alcoholic Effects 0.000 description 1
- 230000002421 anti-septic Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- TZSXPYWRDWEXHG-UHFFFAOYSA-K bismuth;trihydroxide Chemical compound [OH-].[OH-].[OH-].[Bi+3] TZSXPYWRDWEXHG-UHFFFAOYSA-K 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005755 formation reaction Methods 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- 159000000014 iron salts Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000001264 neutralization Effects 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 235000021395 porridge Nutrition 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
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
KAISERLICHESIMPERIAL
PATENTAMT.PATENT OFFICE.
PATENTSCHRIFTPATENT LETTERING
- JVl 187869 KLASSE \2p. GRUPPE- JVl 187869 CLASS \ 2p. GROUP
FRANZ FRITZSCHE & CO. in HAMBURG.FRANZ FRITZSCHE & CO. in Hamburg.
Bekanntlich erhält man beim Eintragen vonIt is well known that when you enter
ο - Oxychinolin in abgekühlte rauchende Schwefelsäure die 8-Oxychinolin-5-sulfosäure (vergl. Journ. für prakt. Chemie N. F., Bd. 41 [1890], S. 33).ο - Oxyquinoline in cooled fuming sulfuric acid is the 8-oxyquinoline-5-sulfonic acid (cf. Journ. for practical chemistry N. F., Vol. 41 [1890], p. 33).
Ferner entsteht bei der Einwirkung von gewöhnlicher konzentrierter Schwefelsäure auf eine alkoholische Lösung von ο - Oxychinolin bei gewöhnlicher Temperatur das saure Sulfat (vergl. Monatshefte für Chemie, Bd. 3 [1882], S. 539) und bei längerem Kochen unter Rückfluß, in Gegenwart von Wasser, 'das neutrale schwefelsaure Salz (vergl. die amerik. Patentschrift 466708).Furthermore, when exposed to ordinary concentrated sulfuric acid, it is produced on an alcoholic solution of ο - oxyquinoline at ordinary temperature that acid sulfate (cf.months booklet for chemistry, vol. 3 [1882], p. 539) and longer Boiling under reflux, in the presence of water, the neutral sulfuric acid salt (See American patent specification 466708).
Es wurde nun gefunden, daß, wenn man ο - Oxychinolin bei einer wenig über dessen Schmelzpunkt (75 bis 760) liegenden Temperatur mit Schwefelsäure von 66° Be. behandelt, es in eine andere Sulfosäure vom Schmelzpunkt 310 bis 3130 übergeführt wird, die Salze bildet, welche ebenso wie sie selbst sich durch wertvolle therapeutische Eigenschaften auszeichnen, und die vermutlich die in der Pharmazeutischen Centralhalle, 35. Bd.It has now been found that if ο - oxyquinoline is used at a temperature slightly above its melting point (75 to 76 0 ) with sulfuric acid of 66 ° Be. treated, it is converted into another sulfonic acid with a melting point of 310 to 313 0 , which forms salts which, like themselves, are characterized by valuable therapeutic properties, and which are presumably the ones in the Pharmaceutical Central Hall, 35th Vol.
(1894), S. 94'95 einer Oxychinolinsulfosäure gegebene Zusammensetzung, nämlich die einer 8-Oxychinolin-7-sulfosäure(1894), p. 94'95 of an oxyquinoline sulfonic acid given composition, namely that of an 8-oxyquinoline-7-sulfonic acid
SO, H- SO, H-
besitzt.owns.
OHOH
5 kg ο - Oxychinolin werden geschmolzen und in 20 kg Schwefelsäure von 66° Be. unter Rühren eingetragen; dabei steigt die Temperatur auf etwa 900. Die Masse bleibt etwa 3 Tage stehen, wobei sie durch Aufbewahrung an einem warmen Orte gegen zu schnelle Abkühlung geschützt wird. Alsdann ist die Bildung der Sulfosäure beendet. Das Reaktionsgemisch wird darauf in ioobis 150 1 Wasser eingetragen; hierbei fällt die Sulfosäure als feines hellgelbes Pulver aus. Dieses wird gewaschen, abgepreßt, getrocknet und zerrieben. Die neue Oxychinolinsulfosäure unterscheidet sich von den bekannten Sulfosäuren durch ihren bei 310 bis 3130 liegenden Schmelzpunkt.5 kg ο - oxyquinoline are melted and in 20 kg sulfuric acid of 66 ° Be. entered with stirring; the temperature rises to about 90 ° . The mass remains there for about 3 days, whereby it is protected against cooling too quickly by storing it in a warm place. The formation of the sulfonic acid is then complete. The reaction mixture is then introduced into 100 to 150 liters of water; the sulfonic acid precipitates out as a fine, light yellow powder. This is washed, pressed, dried and ground. The new Oxychinolinsulfosäure differs from the known sulfonic acids by their at 310-313 0 lying melting point.
Die Säure stellt ein feines kristallinisches citronengelbes Pulver dar und ist sehr schwer löslich in Alkohol und kaltem Wasser, löst sich aber etwas leichter in siedendem Wasser, woraus sie sich beim Abkühlen flockig ausscheidet. In Benzol ist die Sulfosäure unlöslich.The acid is a fine crystalline lemon yellow powder and is very heavy soluble in alcohol and cold water, but dissolves slightly more easily in boiling water, from which it precipitates flaky when it cools. The sulfonic acid is insoluble in benzene.
Das Kaliumsalz C9 H& N(OH) SO3K wird erhalten, indem man molekulare Mengen der Säure und Kali zusammen löst; dasselbe ist leicht löslich in Wasser und scheidet sich aus konzentrierten kochenden Lösungen in Form schöner, atlasglänzender Blättchen ab.The potassium salt C 9 H & N (OH) SO 3 K is obtained by dissolving molecular amounts of the acid and potassium together; it is easily soluble in water and separates out of concentrated boiling solutions in the form of beautiful, atlas-shining leaves.
Auf analoge Weise erhält man z. B. das Natrium-, Barium- und Eisensalz.In an analogous way one obtains z. B. the sodium, barium and iron salts.
Das Natriumsalz C9 H5 N (O H) S O3 Na ist etwas schwerer löslich in Wasser als das Kaliumsalz und kristallisiert in derben Nädelchen.The sodium salt C 9 H 5 N (OH) S O 3 Na is somewhat less soluble in water than the potassium salt and crystallizes in coarse needles.
Das Bariumsalz [C0 /75 N(OH) S O3]2 Ba ist ein schwer lösliches gelbes Pulver.The barium salt [C 0/7 5 N (OH) S O 3] 2 Ba is a sparingly soluble yellow powder.
Das Eisensalz ist schön grün gefärbt und sehr leicht löslich in Wasser.
Das durch Umsetzung des Natriumsalzes mit Silbernitrat darstellbare Silbersalz C9 H5 N(OH) S O3 Ag ist ein unlösliches, hellgelbes,
verhältnismäßig leichtes und lockeres Pulver, welches bei Gegenwart in FäulnisThe iron salt is beautifully green in color and very easily soluble in water.
The silver salt C 9 H 5 N (OH) SO 3 Ag , which can be prepared by reacting the sodium salt with silver nitrate, is an insoluble, light yellow, relatively light and loose powder, which rots when present
ίο übergegangener Stoffe Silber abscheidet, aber in reinem Zustande an Licht und Luft beständig ist.ίο transferred substances silver separates, but is stable in light and air in a pure state.
Das Zinksalz [C0 H5 N(OH) S O3I2 Zn, welches man durch Umsetzung des Natriumsalzes mit Zinkacetat, und nachträglicher Reinigung nach bekannten Methoden, erhält, ist ein gelbliches, in Wasser und Alkohol unlösliches lockeres Pulver.The zinc salt [C 0 H 5 N (OH) SO 3 I 2 Zn, which is obtained by reacting the sodium salt with zinc acetate and subsequently purifying it by known methods, is a yellowish, loose powder that is insoluble in water and alcohol.
Das basische Wismutsalz [CnZZ5 N-OH-S O3Bi (O H)2] erhält man durch iostündiges Digerieren von molekularen Mengen frisch gefällten, rein ausgewaschenen und noch feuchten Wismuthydroxyd und der o-Oxychinolinsulfosäure, welche mit Wasser zu einem dünnen Brei angerührt sind, auf dem Wasserbade. Nach der in üblicher Weise erfolgten Reinigung stellt es ein gelbes, in Wasser und Alkohol unlösliches Pulver dar.The basic bismuth salt [C n ZZ 5 N-OH-S O 3 Bi (OH) 2 ] is obtained by digesting molecular amounts of freshly precipitated, washed-out and still moist bismuth hydroxide and o-oxyquinoline sulfonic acid for 10 hours, which with water to a thin Porridge are mixed on the water bath. After cleaning in the usual way, it turns into a yellow powder that is insoluble in water and alcohol.
Die o-Oxychinolinsulfosäure und.ihre Salze sollen zu . medizinischen, hygienischen und kosmetischen Zwecken Verwendung finden. So besitzt das Silbersalz als Abkömmling der ο - Oxychinolinsulfosäure antiseptische Eigenschaften, und vermag z. B., wie oben erwähnt, in faulenden Flüssigkeiten Silber metallisch abzuscheiden. Das Zinksalz und Wismutsalz sollen für Hautpuder und Salbenzusätze und ähnliche Zwecke, das Wismutsalz auch als Darmdesinfiziens Verwendung finden. Zu denselben Zwecken können auch die anderen Salze, z. B. das Natriumsalz, welches sehr milde wirkt, herangezogen werden.The o-oxyquinoline sulfonic acid and its salts supposed to. find medical, hygienic and cosmetic purposes. The silver salt, as a derivative of ο - oxyquinoline sulfonic acid, is antiseptic Properties, and can z. B., as mentioned above, silver in putrefactive liquids to be deposited metallic. The zinc salt and bismuth salt are said to be used for skin powder and ointment additives and similar purposes, the bismuth salt is also used as an intestinal disinfectant. For the same purposes you can also the other salts, e.g. B. the sodium salt, which has a very mild effect, used will.
-Auch die 8-Oxych.inolin-7-sulfosäure selbst eignet sich wegen ihrer Ungiftigkeit und ihres geringen Geschmackes als innerliches Mittel zur Desinfektion des Darmkanals sowie der Blase und der Harngänge.-Also the 8-Oxych.inolin-7-sulfonic acid itself is suitable because of its non-toxicity and its low taste as an internal means of disinfecting the intestinal tract as well the bladder and urinary tract.
Claims (1)
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE187869C true DE187869C (en) |
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| Country | Link |
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| DE (1) | DE187869C (en) |
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