DE111668C - - Google Patents

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Publication number
DE111668C
DE111668C DENDAT111668D DE111668DA DE111668C DE 111668 C DE111668 C DE 111668C DE NDAT111668 D DENDAT111668 D DE NDAT111668D DE 111668D A DE111668D A DE 111668DA DE 111668 C DE111668 C DE 111668C
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Prior art keywords
uric acid
acid
methyl
parts
mol
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DENDAT111668D
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German (de)
Publication of DE111668C publication Critical patent/DE111668C/de
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    • 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
    • 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
    • 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
    • C07D473/08—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 1 and 3, e.g. theophylline
    • 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
    • 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
    • C07D473/14—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 two methyl radicals in positions 1 and 3 and two methyl radicals in positions 7, 8, or 9

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Saccharide Compounds (AREA)

Description

KAISERLICHESIMPERIAL

PATENTAMT.PATENT OFFICE.

Im Patent 91811 ist unter Beispiel 1 die Darstellung einer Monomethylharnsäure durch Einwirkung von Halogenalkyl auf die wässerig alkalische Lösung der Harnsäure beschrieben. Die so erhaltene Methylharnsäure erwies sich mit der von Hill & Mabery (Berl. Ber. 9, 370) erhaltenen a-Methylharnsäüre identisch und enthält nach weiteren Untersuchungen das Methyl am Stickstoffatom (3) gebunden (vergl. Berl. Ber. 32, 461).In the patent 91811 is under Example 1 Preparation of a monomethyl uric acid by the action of haloalkyl on the aqueous alkaline solution of uric acid is described. The methyl uric acid thus obtained turned out to be identical to that obtained from Hill & Mabery (Berl. Ber. 9, 370) and, according to further investigations, contains the methyl bonded to the nitrogen atom (3) (cf. Berl. Ber. 32, 461).

Es hat sich nun gezeigt, dafs eine neue, zu obiger Methylharnsäure isomere 3-Methylharnsäure erhalten wird, wenn die im Patent 91811 gegebenen Bedingungen für die Alkylirung etwas modificirt werden.It has now been shown that a new 3-methyluric acid isomeric to the above methyluric acid is obtained if the conditions given in patent 91811 for the alkylation be modified somewhat.

Wendet man nämlich bei der Alkylirung nicht, wie im Patent 91811 unter Beispiel 1 angegeben, auf 1 Mol. Harnsäure 2 Mol. Alkali an, sondern bringt auf 1 Mol. Harnsäure nur ι Mol. Alkali zur Verwendung bei Gegenwart von Alkaliacetat, dann wird als Alkylirungsproduct eine Methylharnsäure erhalten, welche sich durch ihre Eigenschaften (Löslichkeit in Wasser, Krystallform u. s. w.) scharf von den bis jetzt bekannten Monomethylharnsäuren unterscheidet, und welche, wie aus der Ueberführbarkeit in das 3 - Methylchlorxanthin nach dem Verfahren des Patentes 99123 hervorgeht, das Methyl am Stickstoffatom (3) enthalten mufs.This is because it is not used in the alkylation, as in patent 91811 under Example 1 stated, to 1 mol. uric acid adds 2 mol. alkali, but brings to 1 mol. uric acid only ι Mol. Alkali for use in the presence of alkali acetate, then is used as alkylation product a methyl uric acid obtained, which is characterized by its properties (solubility in Water, crystal form, etc.) sharp from the monomethyl uric acids known up to now differs, and which, as can be seen from the convertibility into 3-methylchlorxanthine the process of patent 99123, which must contain methyl on the nitrogen atom (3).

Von dem im Patent 92310 beschriebenen Alkylirungsverfahren unterscheidet sich das vorliegende dadurch, dafs dort bei Gegenwart von Natriumacetat oder ähnlichen Salzen die freie Harnsäure in wässeriger Suspension dem Alkylirungsmittel dargeboten wird, während bei der gegenwärtigen Erfindung ein harnsaures Salz in Lösung der Einwirkung von Methyljodid ausgesetzt ist; infolge dessen wird auch nach dem Verfahren des Patentes 92310 ein anderes Endproduct erhalten, nämlich hauptsächlich die alte 3 - Methylharnsäure, identisch mit der a-Methylharnsäure.This differs from the alkylation process described in patent 92310 present by the fact that there, in the presence of sodium acetate or similar salts, the free uric acid in aqueous suspension is presented to the alkylating agent, while in the present invention, a uric acid salt in solution under the action of Exposed to methyl iodide; as a result, the procedure of patent 92310 get another end product, namely mainly the old 3 - methyl uric acid, identical to a-methyl uric acid.

Zur Erläuterung des Verfahrens diene folgendes Beispiel:The following example is used to explain the procedure:

50 Theile Harnsäure werden mit 3500 Theilen kochenden Wassers und 30 Theilen 8oproc. Aetzkali (ΐ'/.2 Mol.) zur Lösung gebracht, mit 18 Theilen 5oproc. Essigsäure (x/2 Mol.) versetzt und die klare Lösung in einen mit Rührwerk versehenen Autoclaven gefüllt; in denselben preist man 22 Theile Chlormethyl (1Y2 Mol.) und erhitzt während 5 Stunden auf ioo°. Nach dem Erkalten wird das abgeschiedene krystallisirte Reactionsproduct, welches aus einem Gemenge von unveränderter Harnsäure und der neuen 3-Methylharnsäure besteht, abgesaugt und mit Wasser ausgewaschen. 50 parts uric acid are mixed with 3500 parts boiling water and 30 parts 8oproc. Caustic potash ('/. 2 mol.) Brought to solution, with 18 parts 5oproc. Acetic acid ( x / 2 mol.) Is added and the clear solution is poured into an autoclave equipped with a stirrer; 22 parts of chloromethyl (1Y 2 mol.) are priced in the same and heated to 100 ° for 5 hours. After cooling, the precipitated crystallized reaction product, which consists of a mixture of unchanged uric acid and the new 3-methyluric acid, is suctioned off and washed out with water.

Zur Entfernung der Harnsäure führt man die gesammte Masse in das Mononatriumsalz über, wobei das schwer lösliche Salz der Harnsäure abgeschieden wird. Aus seinem Filtrat wird durch Ansäuern mit einer Mineralsäure die Methylharnsäure, welche bei richtig durchge-To remove the uric acid, the entire mass is introduced into the monosodium salt over, whereby the poorly soluble salt of uric acid is deposited. Its filtrate becomes by acidification with a mineral acid, the methyl uric acid, which when properly

führter Trennung nur noch Spuren von Harnsäure enthält, als fein krystallisirter Niederschlag erhalten.after separation only contains traces of uric acid, as a finely crystallized precipitate obtain.

Zur völligen Reinigung wird sie am besten in das krystallisirte Kalisalz verwandelt, indem man ι Theil der Säure in der ι ο fachen Volumenmenge Doppelnormal-Kalilauge löst und diese Lösung zunächst mit dem gleichen Volumen Feinsprit allmählich versetzt. Hierbei scheidet sich etwa noch vorhandene Harnsäure als Monokalisalz aus; nach seiner Entfernung werden noch 5 Vol.-Theile Feinsprit zugegeben und das Ganze längere Zeit stehen gelassen. Es krystallisirt nun das Kalisalz der Methylharnsäure in langen, asbestartig verfilzten Nadeln aus, welche die Flüssigkeit breiartig erfüllen.For complete purification it is best transformed into the crystallized potassium salt by one part of the acid in one part by volume Dissolve double normal potassium hydroxide solution and gradually add the same volume of fine spirit to this solution. This separates any remaining uric acid turns out to be a monopali salt; after its removal 5 parts by volume of fine spirit are added and the whole is left to stand for a long time. The potassium salt of methyl uric acid now crystallizes in long, asbestos-like matted layers Needles that fill the liquid like a mush.

Aus diesem Kalisalz wird die neue 3 - Methylharnsäure durch Mineralsäuren abgeschieden und nach Lösen in siedendem Wasser in völlig reinem Zustande erhalten.The new 3 - methyl uric acid is separated from this potassium salt by means of mineral acids and obtained in a completely pure state after dissolving in boiling water.

Die Säure löst sich in 570 bis 600 Theilen siedenden Wassers und krystallisirt scharf mit ι Mol. Wasser, welches beim längeren Erhitzen auf 120° entweicht; sie unterscheidet sich hierdurch von der bis jetzt bekannten 3-Methylharnsäure, die zur Lösung 250 Theile siedenden Wassers benöthigt und nach dem Trocknen bei ioo° noch Y2 Mol. Wasser enthält.The acid dissolves in 570 to 600 parts of boiling water and crystallizes sharply with 1 mole of water, which escapes on prolonged heating at 120 °; in this way it differs from the previously known 3-methyluric acid, which requires 250 parts of boiling water to dissolve it and, after drying at 100 °, still contains Y 2 moles of water.

Das Product soll als Ausgangsmaterial zur Herstellung chemisch-pharmaceutischer Präparate dienen. 'The product should be used as the starting material for Manufacture of chemical-pharmaceutical preparations are used. '

Claims (1)

Patent-Anspruch:Patent claim: Verfahren zur Darstellung einer 3-Methylharnsäure unter Benutzung des durch das Patent 91811 geschützten Verfahrens, dadurch gekennzeichnet, dafs man Halogenmethyl auf die Lösung eines sauren harnsauren Alkalisalzes bei Gegenwart von Alkaliacetat einwirken läfst.Method for the preparation of a 3-methyluric acid using the by the Patent 91811 protected process, thereby characterized that one halomethyl on the solution of an acidic uric acid alkali salt can act in the presence of alkali acetate.
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