DE916950C - Process for the production of a crystallized penicillin salt which is sparingly soluble in water - Google Patents

Process for the production of a crystallized penicillin salt which is sparingly soluble in water

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Publication number
DE916950C
DE916950C DEF7418A DEF0007418A DE916950C DE 916950 C DE916950 C DE 916950C DE F7418 A DEF7418 A DE F7418A DE F0007418 A DEF0007418 A DE F0007418A DE 916950 C DE916950 C DE 916950C
Authority
DE
Germany
Prior art keywords
penicillin
salt
water
crystallized
production
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
DEF7418A
Other languages
German (de)
Inventor
Dr Klaus Bauer
Dr Rudolf Hiltmann
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.)
Bayer AG
Original Assignee
Bayer 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
Application filed by Bayer AG filed Critical Bayer AG
Priority to DEF7418A priority Critical patent/DE916950C/en
Application granted granted Critical
Publication of DE916950C publication Critical patent/DE916950C/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

Verfahren zur Herstellung eines in Wasser schwer löslichen kristallisierten Penicillinsalzes Es ist bekannt, Penicillin für therapeutische !wecke als Salz des p-Aminobenzoesäurediäthylaminoäthylesters (Procain-Penicillin) zu verwenden. Dieses Salz hat gegenüber dem Penicillin-Natrium bzw. -Kalium Vorteile, da es eine protrahierte Wirkung hat, d. h. der Penicillinspiegel im Blut länger erhalten bleibt. Das Salz aus p-Aminohenzoesäurediäthylaminoäthylester und Penicillin ist in Wasser schwer löslich. Auf diese Schwerlöslichkeit wird seine Beständigkeit und die protrahierte Wirkung zurückgeführt.Process for the preparation of a crystallized one that is sparingly soluble in water Penicillin Salt It is known to use penicillin for therapeutic purposes as the salt of the p-aminobenzoic acid diethylaminoethyl ester (procaine penicillin) to be used. This Salt has advantages over penicillin sodium or potassium, as it has a protracted effect Has an effect, d. H. the penicillin level in the blood is maintained longer. The salt from p-Aminohenzoesäurediethylaminoäthylester and penicillin is difficult in water soluble. On this poor solubility is its stability and that of the protracted Effect.

Es wurde nun gefunden, daß Penicillin mit Phthalimido-N-äthvlisothioharnstoff ein Salz zu bilden vermag, das in Wasser erheblich schwerer löslich ist als das bekannte Procain-Penicillin und das außerdem gut kristallisiert ist. Die Herstellung des Salzes erfolgt erfindungsgemäß dadurch, daß Penicillin oder ein Penicillinsalz mit Phthalimido-N-äthylisothioharnstoff oder einem Salz dieser Base umgesetzt wird und das entstehende schwer lösliche Penicillinsalz in an sich bekannter Weise isoliert wird. Als besonders geeignet hat sich für die Umsetzung das Penicillin G erwiesen. Die protrahierte Wirkung des Penicillinsalzes des Phthalimido-N-äthylisothioharnstoffs ist gegenüber der des Procain-Penicillins noch erhöht.It has now been found that penicillin is able to form a salt with phthalimido-N-ether isothiourea which is considerably less soluble in water than the known procaine penicillin and which is also well crystallized. According to the invention, the salt is prepared by using penicillin or a penicillin salt with phthalimido-N-ethylisothiourea or a salt of this base is reacted and the resulting poorly soluble penicillin salt is isolated in a manner known per se. Penicillin G has proven to be particularly suitable for the implementation. The protracted effect of the penicillin salt of phthalimido-N-ethylisothiourea is even greater than that of procaine penicillin.

Das Penicillinsalz des genannten Phthalimido-N-äthylisothioharnstoffs kann in wäßriger oder öliger Suspension angewendet werden, wobei gegebenenfalls an sich bekannte resorptionsverzögernde Zusätze wie Bienenwachs oder andere Wachse oder Aluminiummonostearat verwendet werden können.The penicillin salt of the phthalimido-N-ethylisothiourea mentioned can be in aqueous or oily suspension are applied, whereby optionally known absorption-retarding additives such as beeswax or other waxes or aluminum monostearate can be used.

Ferner kann dieses in Wasser schwer lösliche Salz des Penicillins mit dem genannten Phthalimido-N-äthvlisothioharnstoff dazu verwendet werden, Penicillin aus seinen Lösungen zu isolieren und auf diese Weise zu reinigen.This salt of penicillin, which is sparingly soluble in water, can also be used with the mentioned phthalimido-N-äthvlisothiourea are used to penicillin to isolate from its solutions and to purify in this way.

Die Zahl der organischen Basen, welche mit Penicillin in Wasser schwer lösliche und kristallisierte Salze bilden, ist gering. Es ist daher als eine wesentliche Bereicherung der Technik anzusehen, wenn erfindungsgemäß die Herstellung eines neuen therapeutisch verwertbaren Penicillinsalzes mit höherer Depotwirkung ermöglicht wird.The number of organic bases which are difficult to use with penicillin in water Forming soluble and crystallized salts is low. It is therefore considered an essential Enrichment of technology to be seen when inventing the manufacture of a new one allows therapeutically usable penicillin salt with a higher depot effect will.

Beispiel 3,30 g Phthalimido-N-äthylisothiuroniumbromid werden in der eben nötigen Menge warmen Wassers gelöst und mit einer kalten Lösung von 3,56 g Penicillin-G-Natrium in 15 ccm Wasser versetzt. Nach kurzer Zeit kristallisiert das Penicillin-G-Salz des Phthalimido-N-äthylisothioharnstofs aus. Es wird abgesaugt, mit wenig Wasser gewaschen und getrocknet. F. = i46°. Wirksamkeit ioo i. E./mg. EXAMPLE 3.30 g of phthalimido-N-ethylisothiuronium bromide are dissolved in the just necessary amount of warm water and mixed with a cold solution of 3.56 g of penicillin G sodium in 15 cc of water. After a short time, the penicillin G salt of phthalimido-N-ethylisothiourea crystallizes out. It is filtered off with suction, washed with a little water and dried. F. = i46 °. Effectiveness ioo i. E./mg.

Das Phthalimido-N-äthylisathiuroniumbromid erhält man in üblicher Weise aus Phthalimido-N-äthylbromid und Thioharnsto -f. F. = a4obisz4a'.The phthalimido-N-ethylisathiuronium bromide is obtained in the usual way Way from phthalimido-N-ethyl bromide and thiourea -f. F. = a4obisz4a '.

Claims (1)

PATENTANSPRÜCHE: i. Verfahren zur Herstellung eines in Wasser schwer löslichen kristallisierten Penicillinsalzes, dadurch gekennzeichnet, daß Penicillin oder ein Penicillinsalz mit Phthalimido-N-äthylisothioharnstoff oder einem Salz dieser Base umgesetzt wird und das entstehende schwer lösliche Penicillinsalz in an sich bekannter Weise isoliert wird. a. Verfahren nach Anspruch i, dadurch gekennzeichnet, daß als Penicilin das Penicillin G verwendet wird.PATENT CLAIMS: i. Method of making a heavy in water soluble crystallized penicillin salt, characterized in that penicillin or a penicillin salt with phthalimido-N-ethylisothiourea or a salt this base is implemented and the resulting poorly soluble penicillin salt in is isolated in a known manner. a. Method according to claim i, characterized in that that penicillin G is used as penicilin.
DEF7418A 1951-10-26 1951-10-26 Process for the production of a crystallized penicillin salt which is sparingly soluble in water Expired DE916950C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DEF7418A DE916950C (en) 1951-10-26 1951-10-26 Process for the production of a crystallized penicillin salt which is sparingly soluble in water

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEF7418A DE916950C (en) 1951-10-26 1951-10-26 Process for the production of a crystallized penicillin salt which is sparingly soluble in water

Publications (1)

Publication Number Publication Date
DE916950C true DE916950C (en) 1954-08-23

Family

ID=7085439

Family Applications (1)

Application Number Title Priority Date Filing Date
DEF7418A Expired DE916950C (en) 1951-10-26 1951-10-26 Process for the production of a crystallized penicillin salt which is sparingly soluble in water

Country Status (1)

Country Link
DE (1) DE916950C (en)

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