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DE1493600A1 - Process for the production of N-acetylcysteine - Google Patents

Process for the production of N-acetylcysteine

Info

Publication number
DE1493600A1
DE1493600A1 DE19651493600 DE1493600A DE1493600A1 DE 1493600 A1 DE1493600 A1 DE 1493600A1 DE 19651493600 DE19651493600 DE 19651493600 DE 1493600 A DE1493600 A DE 1493600A DE 1493600 A1 DE1493600 A1 DE 1493600A1
Authority
DE
Germany
Prior art keywords
acetylcysteine
production
cysteine
solution
acetylation
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.)
Pending
Application number
DE19651493600
Other languages
German (de)
Inventor
Stark Dr Adolf
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.)
Diamalt AG
Original Assignee
Diamalt 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 Diamalt AG filed Critical Diamalt AG
Publication of DE1493600A1 publication Critical patent/DE1493600A1/en
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton
    • C07C323/59—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton with acylated amino groups bound to the carbon skeleton
    • 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
    • A61K31/185—Acids; Anhydrides, halides or salts thereof, e.g. sulfur acids, imidic, hydrazonic or hydroximic acids
    • A61K31/19—Carboxylic acids, e.g. valproic acid
    • A61K31/195—Carboxylic acids, e.g. valproic acid having an amino group
    • A61K31/197—Carboxylic acids, e.g. valproic acid having an amino group the amino and the carboxyl groups being attached to the same acyclic carbon chain, e.g. gamma-aminobutyric acid [GABA], beta-alanine, epsilon-aminocaproic acid or pantothenic acid
    • A61K31/198—Alpha-amino acids, e.g. alanine or edetic acid [EDTA]
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/57—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups
    • C07C323/58—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being further substituted by nitrogen atoms, not being part of nitro or nitroso groups with amino groups bound to the carbon skeleton

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

9360093600

Verfahren zur Herstellung von N-AcetylcysteinProcess for the production of N-acetylcysteine

Es lag nahe, bei der Herstellung von N-Acetylcystein von Cystein auszugehen und dieses in an sich bekannter Weise zu acctylieren. Diese Arbeitsweise ist jedoch umständlich und unwirtschaftlich, weil sie zunächst die Reinherstellung von Cystein verlangt.It made sense to start with cysteine in the production of N-acetylcysteine and to add this in a manner known per se acctylate. However, this method of working is cumbersome and uneconomical because it initially involves pure production required of cysteine.

Es wurde nun gefunden, dass man auf einfachem und sicherem iVeg zu Acetylcystein kommt, wenn man vom Cystin ausgeht, dieses in an sich bekannter V/eise, zweckmässig in saurer Lösung an einer ^uucksilber-ivathode elektrolytisch, zu Cystein reduziert und ohne Ausfällung des Cysteins bzw. des Cysteinhydrochlorids die Acetylierung durchführt.It has now been found that one can get to acetylcysteine on a simple and safe iVeg if one starts with cystine, this one Electrolytically reduced to cysteine in a manner known per se, expediently in acidic solution on a silver iv cathode and carries out the acetylation without precipitation of the cysteine or the cysteine hydrochloride.

Ausführungsbeispiel:Embodiment:

7 L.c Cystin v/erden in saurer Lösung elektrolytisch reduziert. Die erhaltene Cysteinhydrochloridlösung wird dann mit Aktivkohle behandelt, wodurch eine farblose, klare Lösung von Cycteinhydrochlorid erhalten wird. Anschließend wird mit Konzentrierter Natronlauge bis pH 5»o neutralisiert, wobei ein xoil dos J:, ;:.teins ausfällt. In die unter iiühren auf 20° C abp;ei:ühlte Losung bzv/. ouspension werden nunmehr 10 Liter Essigcäureanli7/drid langsam zugegeben, hierbei soll die Temperatur 20° nicht v/o cent lieh überschreiten. Nach etwa 2 Stunden ist die Zugabe beendet. Ks v/ird nun unter Zufügung von 200 g Aktivkohle noch 1 stunde weitergerührt· Nach Filtration der Lösung wird diese im Vakuum und zwar bis auf 75 ßef° eingedampft, wobei sich Kochsalz abscheidet, das abfiltriert v/ird. Dac i'lltrat v/ird dann zweckmässig auf 70 Ref° durch Zugabe von dest...as3er eingestellt und unter Kühlung ca. 12 Stunden ' f-;erührt. Hierbei scheidet 3ich das Acetylcystein in7 L.c cystine v / ground electrolytically reduced in acidic solution. The resulting cysteine hydrochloride solution is then treated with activated charcoal, creating a colorless, clear solution from cyctein hydrochloride. It is then neutralized with concentrated sodium hydroxide solution to pH 5 »o, with a xoil dos J :,;:. teins fails. In the under stirring to 20 ° C abp; ei: ühlte solution or /. The suspension will now be 10 liters of acetic acid anli7 / drid added slowly, in this case the temperature should not exceed 20 ° v / o cent borrowed. After about 2 hours the addition is over. Ks v / ird now with the addition of 200 g Activated charcoal stirred for a further 1 hour · After filtering the Solution, this is evaporated in a vacuum up to 75 ßef °, whereby common salt separates out, which is filtered off. The acid is then expediently increased to 70 Ref ° by adding set by least ... as3er and cool for approx. 12 hours' f-; it touches. Here the acetylcysteine separates into

909821/1089909821/1089

_ 2 _ U93600_ 2 _ U93600

einer Menge von ca. IO Kg aus. Die angefallenen Mutterlaugen werden der nächsten Verarbeitung wieder zugegeben. Das auskristallisierte Rohprodukt wird in bekannter Weise durch Umkristallisation gereinigt.an amount of approx. 10 kg. The accumulated mother liquors are added to the next processing. The crystallized crude product is made in a known manner purified by recrystallization.

Claims (2)

Patentansprüche:Patent claims: 1.) Verfahren zur Herstellung von N-Acetylcystein dadurch gekennzeichnet, dass in einem Arbeitsgang Cystin zweckiriässig elektrolytisch in saurer Lösung reduziert wird und ohne Isolierung des entstandenen Cysteinhydrochlorids bzw. des Cysteins die Acetylierung mit Essigsäureanhydrid durchgeführt wird.1.) Process for the production of N-acetylcysteine thereby marked that cystine is expedient in one operation is reduced electrolytically in acidic solution and without isolation of the resulting cysteine hydrochloride or the Cysteine acetylation is carried out with acetic anhydride. 2.) Verfahren nach Anspruch 1) dadurch gekennzeichnet, dass die Acetylierung bei niedrigen Temperaturen, die 20° G nicht merklich überschreiten sollen, durchgeführt wird.2.) Method according to claim 1) characterized in that acetylation at low temperatures, not 20 ° G should noticeably exceed, is carried out. 909821/1089909821/1089
DE19651493600 1965-03-18 1965-03-18 Process for the production of N-acetylcysteine Pending DE1493600A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DED0046823 1965-03-18

Publications (1)

Publication Number Publication Date
DE1493600A1 true DE1493600A1 (en) 1969-05-22

Family

ID=7049971

Family Applications (1)

Application Number Title Priority Date Filing Date
DE19651493600 Pending DE1493600A1 (en) 1965-03-18 1965-03-18 Process for the production of N-acetylcysteine

Country Status (1)

Country Link
DE (1) DE1493600A1 (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011263A (en) * 1975-07-04 1977-03-08 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of n-acetyl-l-methionine
EP0304778A1 (en) * 1987-08-21 1989-03-01 Degussa Aktiengesellschaft Process for the production of N-acylated mercapto-alpha-amino acids

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4011263A (en) * 1975-07-04 1977-03-08 Deutsche Gold- Und Silber-Scheideanstalt Vormals Roessler Process for the production of n-acetyl-l-methionine
EP0304778A1 (en) * 1987-08-21 1989-03-01 Degussa Aktiengesellschaft Process for the production of N-acylated mercapto-alpha-amino acids

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Legal Events

Date Code Title Description
SH Request for examination between 03.10.1968 and 22.04.1971