DE625995C - Process for the preparation of heavy metal compounds of thio-substituted carbohydrates - Google Patents

Process for the preparation of heavy metal compounds of thio-substituted carbohydrates

Info

Publication number
DE625995C
DE625995C DESCH94940D DESC094940D DE625995C DE 625995 C DE625995 C DE 625995C DE SCH94940 D DESCH94940 D DE SCH94940D DE SC094940 D DESC094940 D DE SC094940D DE 625995 C DE625995 C DE 625995C
Authority
DE
Germany
Prior art keywords
thio
parts
heavy metal
preparation
metal compounds
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
Application number
DESCH94940D
Other languages
German (de)
Inventor
Dr Hans-Georg Allardt
Dr Adolf Feldt
Walter Schoeller
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Schering Kahlbaum AG
Original Assignee
Schering Kahlbaum AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority to DEC37852D priority Critical patent/DE527036C/en
Priority to GB3042/27A priority patent/GB293363A/en
Priority to AT129303D priority patent/AT129303B/en
Application filed by Schering Kahlbaum AG filed Critical Schering Kahlbaum AG
Priority to DESCH94940D priority patent/DE625995C/en
Priority to DESCH94941D priority patent/DE573629C/en
Priority to AT144025D priority patent/AT144025B/en
Priority to GB19617/32A priority patent/GB386562A/en
Priority to GB20293/32A priority patent/GB397293A/en
Application granted granted Critical
Publication of DE625995C publication Critical patent/DE625995C/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07HSUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H23/00Compounds containing boron, silicon, or a metal, e.g. chelates, vitamin B12

Description

Verfahren zur Darstellung von Schwermetallverbindungen von thiosubstituierten Kohlenhydraten Nach dem Patent 527 036 erhält man therapeutisch wertvolle Metallmercaptoverbindungen in der Weise, daß man thiosubstituierte Kohlenhydrate in saurem oder neutralem Milieu mit Schwermetallcalzen umsetzt.Process for the preparation of heavy metal compounds of thio-substituted ones Carbohydrates According to patent 527 036, therapeutically valuable metal mercapto compounds are obtained in such a way that you can use thio-substituted carbohydrates in an acidic or neutral environment implemented with heavy metal lime.

Es wurde nur. gefunden, daß man vorteilhaft auch so verfahren kann, daß man Alkali- und Erdalkalisalze der thiosubstituierten Kohlenhydrate mit Schwermetallsalzen umsetzt.It just got. found that one can also advantageously proceed in this way, that one alkali and alkaline earth salts of the thio-substituted carbohydrates with heavy metal salts implements.

Beispiel i i,62 Teile i-Natriumthioglucose wird in 5o Teilen Wasser gelöst und unter Rühren allmählich eine Lösung von 5,g2 Teilen Kaliumaurobromid oder 3,03 Teilen Goldchlorid in 3o Teilen Wasser bei 6 bis io° zugetropft.Example ii, 62 parts of i-sodium thioglucose is dissolved in 50 parts of water and a solution of 5. g2 parts of potassium aurobromide or 3.03 parts of gold chloride in 30 parts of water at 6 to 10 ° is gradually added dropwise, with stirring.

Es beginnt bald die Ausscheidung der Aurothioglucose. Nachdem alles zugeflossen ist, rührt man noch 1/2 Stunde und saugt den ausgeschiedenen Niederschlag ab, wäscht ihn wiederholt mit Wasser gut aus und trocknet ihn durch Waschen mit. Alkohol und Äther. -Schließlich wird die Verbindung im Vakuum über Phosphorpentoxyd bis zur Gewichtskonstanz getrocknet.The excretion of aurothioglucose soon begins. After everything has flowed in, the mixture is stirred for a further 1/2 hour and the precipitate which has separated out is filtered off with suction , washes it repeatedly with water and dries it with washing. Alcohol and ether. -Finally, the compound is in vacuo over phosphorus pentoxide dried to constant weight.

Analog verfährt man bei der Darstellung anderer Schwermetallverbindungen von thiosubstituierten Kohlenhydraten.The same applies to the representation of other heavy metal compounds of thio-substituted carbohydrates.

Statt der Natriumsalze kann man die äquivalente Menge anderer Alkali- oder Erdalkälisalze der thiosubstituierten Kohlenhydrate anwenden.Instead of the sodium salts, you can use the equivalent amount of other alkali or use alkaline earth salts of thio-substituted carbohydrates.

Beispiel 2 443 Teile Natriümthioglucose wurden in 3o Teilen Wasser suspendiert und unter Rühren i2,3 Teile Antimontrichlorid eingetragen. Nach 1/_stündigem Ruhen ist vollständige Umsetzung erfolgt und eine klare Lösung entstanden. Bei Zugabevon 3oo Teilen absoluten Alkohols scheidet sich dieAntimoilthioglucose zunächst als Öl ab, das abgetrennt wird und beim Verreiben mit Alkohol erstarrt. Zur Trennung vom entstandenen Kochsalz löst man :lie Substanz unter gelindem Erwärmen in 4o Teilen Glykol, saugt vorn ungelösten Kochsalz ab und fällt die Antimonthioglucose durch Zugabe von q.oo Teilen Alkohol. Nach nochmaliger Wiederholung dieser Operation ist die Substanz frei von Kochsalz und rein. Die Substanz wird mit Äther zur Entfernung des Glykols gut gewaschen und dann im Vakuum bei 70° getrocknet. Die Substanz ist ein weißes Pulver, leicht löslich im Wasser, mäßig leicht in heißem Methylalkohol, unlöslich in Äther und Chloroform. Statt in wässeriger Lösung kann man von vornherein in Glykol arbeiten. Zu diesem Zweck wird die Natriumthioglucose statt in Wasser in Glykol suspendiert. In die gelinde erwärmte Suspension trägt,man das Antimontrichlorid allmählich ein.Example 2 443 parts of sodium thioglucose were dissolved in 30 parts of water suspended and added i2.3 parts of antimony trichloride with stirring. After 1 / _ hour Rest has been fully implemented and a clear solution has emerged. When adding 300 parts of absolute alcohol, the antimoilthioglucose initially separates as Oil that is separated off and solidifies when rubbed with alcohol. For separation Dissolve the resulting common salt in 40 parts with gentle warming Glycol, sucks in front of undissolved common salt and the antimony thioglucose falls by adding q, ooo parts of alcohol. After repeating this operation again the substance is free of table salt and pure. The substance is removed with ether of the glycol washed well and then dried in vacuo at 70 °. The substance is a white powder, easily soluble in water, moderately easily in hot methyl alcohol, insoluble in ether and chloroform. Instead of using an aqueous solution, you can do this right from the start work in glycol. For this purpose the sodium thioglucose is used instead of in water suspended in glycol. Antimony trichloride is added to the mildly heated suspension gradually a.

Durch Umsetzen von 39,6 Teilen Kaliumthiocellobiose mit 12 Teilen Antimontribromid erhält man ganz analog das Antimonsalz der Thiocellobiose.By reacting 39.6 parts of potassium thiocellobiose with 12 parts Antimony tribromide is obtained quite analogously to the antimony salt of thiocellobiose.

Beispiel 3 Verwendet man in obigem Beispiel statt des Antimontrichlorids 17 Teile Wisinuttrichlorid und verfährt sonst sinngemäß, so erhält man die schon im Hauptpatent näher beschriebene 1-Wismutthioglucose.Example 3 Is used in the above example instead of antimony trichloride 17 parts of Wisinuttrichlorid and otherwise proceed in the same way, this is what you get 1-bismuth thioglucose described in more detail in the main patent.

Beispiel q.Example q.

Zu einer Lösung won q.1,6 Teilen Natrium-Z> in too Teilen Wasser läßt man unter guter Kühlung auf 5 ° unter Rühren eine Lösung von 19,7 Teilen Kaliumgoldbromid in Zoo Teilen Wasser langsam zutropfen und rührt dann noch 1J2 Stunde weiter. Man säuert dann mit wenig Salzsäure .eben an und saugt die ausgeschiedene Aurothiocellobiose ab, die zur Entfernung des Salzes erst mit Wasser und dann mit Alkohol und Äther gewaschen und bis 65' im Vakuumgetrocknet wird. Die Substanz ist ein w=eißes, schwach gelbstichiges, amorphes Pulver, ist wenig löslich in Wasser, unlöslich in organischen Medien.To a solution of 1.6 parts of sodium Z> in too parts of water, a solution of 19.7 parts of potassium gold bromide in zoo parts of water is slowly added dropwise with good cooling to 5 ° with stirring, and the mixture is then stirred for a further 1/2 hour. It is then acidified with a little hydrochloric acid and the precipitated aurothiocellobiose is sucked off, which is first washed with water and then with alcohol and ether and dried in vacuo to 65 ' to remove the salt. The substance is a white, slightly yellowish, amorphous powder, is sparingly soluble in water, insoluble in organic media.

Beispiel 5 23,4 Teile wasserfreie Kaliumthiogalaktose werden in Zoo Teilen Wasser gelöst und, ähnlich wie im Beispiel q., mit einer Lösung von 16,9 Teilen Silbernitrat in too 'feilen Wasser versetzt. Dabei fällt nach einiger Zeit die Silberthiogalaktose als weißer voluminöser Niederschlag aus. Sie wird abgesaugt und wie oben mit Wasser, Alkohol und Äther gewaschen. Die Substanz ist ein weißes Pulver, schwer löslich in kaltem Wasser, leichter in der Wärme,. unlöslich in organischen Medien.Example 5 23.4 parts of anhydrous potassium thiogalactose are used in Zoo Part of water and dissolved, similar to Example q., With a solution of 16.9 Share silver nitrate in too 'filing water. It falls after a while the silver thiogalactose as a white voluminous precipitate. She is sucked off and washed with water, alcohol and ether as above. The substance is a white one Powder, sparingly soluble in cold water, lighter in heat. insoluble in organic Media.

Claims (1)

PATENTANSPRUCH: Abänderung des durch Patent 527 036 geschützten Verfahrens zur Darstellung von Schwermetallverbindungen von thiosubstituierten Kohlenhydraten, dadurch gekennzeichnet, daß man hier Alkali-oder Erdalkalisalze von thiosubstituierten Kohlenhydraten mit Schwermetallsalzen umsetzt.PATENT CLAIM: Modification of the process protected by patent 527 036 for the preparation of heavy metal compounds of thio-substituted carbohydrates, characterized in that alkali or alkaline earth salts of thio-substituted carbohydrates are reacted with heavy metal salts.
DESCH94940D 1926-02-18 1931-08-04 Process for the preparation of heavy metal compounds of thio-substituted carbohydrates Expired DE625995C (en)

Priority Applications (8)

Application Number Priority Date Filing Date Title
DEC37852D DE527036C (en) 1926-02-18 1926-02-18 Process for the preparation of water-soluble metal mercapto compounds
GB3042/27A GB293363A (en) 1926-02-18 1927-02-02 The manufacture of new metallo mercapto compounds
AT129303D AT129303B (en) 1926-02-18 1927-02-12 Process for the preparation of water-soluble metal mercapto compounds.
DESCH94940D DE625995C (en) 1926-02-18 1931-08-04 Process for the preparation of heavy metal compounds of thio-substituted carbohydrates
DESCH94941D DE573629C (en) 1926-02-18 1931-08-04 Process for the preparation of complex compounds of thio-substituted carbohydrates
AT144025D AT144025B (en) 1926-02-18 1932-07-01 Process for the preparation of water-soluble metal mercapto compounds.
GB19617/32A GB386562A (en) 1926-02-18 1932-07-11 Process for the manufacture of heavy metal compounds of thio-substituted carbohydrates
GB20293/32A GB397293A (en) 1926-02-18 1932-07-18 Process for the manufacture of complex double compounds of thio-substituted carbohydrates

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DEC37852D DE527036C (en) 1926-02-18 1926-02-18 Process for the preparation of water-soluble metal mercapto compounds
DESCH94940D DE625995C (en) 1926-02-18 1931-08-04 Process for the preparation of heavy metal compounds of thio-substituted carbohydrates

Publications (1)

Publication Number Publication Date
DE625995C true DE625995C (en) 1936-02-20

Family

ID=34066198

Family Applications (2)

Application Number Title Priority Date Filing Date
DEC37852D Expired DE527036C (en) 1926-02-18 1926-02-18 Process for the preparation of water-soluble metal mercapto compounds
DESCH94940D Expired DE625995C (en) 1926-02-18 1931-08-04 Process for the preparation of heavy metal compounds of thio-substituted carbohydrates

Family Applications Before (1)

Application Number Title Priority Date Filing Date
DEC37852D Expired DE527036C (en) 1926-02-18 1926-02-18 Process for the preparation of water-soluble metal mercapto compounds

Country Status (3)

Country Link
AT (2) AT129303B (en)
DE (2) DE527036C (en)
GB (2) GB386562A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE949055C (en) * 1951-09-06 1956-09-13 Rheinpreussen Ag Process for the production of heavy metal complex compounds of ª ‡, ª ‡ -Dimercaptosuccinic acid

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2440729A (en) * 1944-03-25 1948-05-04 Du Pont Water-soluble heavy metal salts of thiosorbitol and other monothio sugar alcohols
US2518135A (en) * 1946-11-01 1950-08-08 Univ Ohio State Res Found Uniformly 2-substituted glucopyranose polymers
US4918175A (en) * 1988-06-21 1990-04-17 Marion Laboratories, Inc. Bismuth (phosph/sulf)ated saccharides

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE949055C (en) * 1951-09-06 1956-09-13 Rheinpreussen Ag Process for the production of heavy metal complex compounds of ª ‡, ª ‡ -Dimercaptosuccinic acid

Also Published As

Publication number Publication date
DE527036C (en) 1931-06-24
AT129303B (en) 1932-07-25
GB386562A (en) 1933-01-19
AT144025B (en) 1935-12-27
GB397293A (en) 1933-08-24

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