DE1011880B - Process for the production of low-toxicity salts of basic Streptomyces antibiotics - Google Patents
Process for the production of low-toxicity salts of basic Streptomyces antibioticsInfo
- Publication number
- DE1011880B DE1011880B DEC12428A DEC0012428A DE1011880B DE 1011880 B DE1011880 B DE 1011880B DE C12428 A DEC12428 A DE C12428A DE C0012428 A DEC0012428 A DE C0012428A DE 1011880 B DE1011880 B DE 1011880B
- Authority
- DE
- Germany
- Prior art keywords
- panthenol
- basic
- sulfate
- production
- low
- 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
Links
- 239000003242 anti bacterial agent Substances 0.000 title claims description 11
- 229940088710 antibiotic agent Drugs 0.000 title claims description 11
- 241000187747 Streptomyces Species 0.000 title claims description 10
- 238000000034 method Methods 0.000 title claims description 8
- 150000003839 salts Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title claims description 3
- 231100000053 low toxicity Toxicity 0.000 title 1
- 229940101267 panthenol Drugs 0.000 claims description 23
- 235000020957 pantothenol Nutrition 0.000 claims description 23
- 239000011619 pantothenol Substances 0.000 claims description 23
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 claims description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- GHOKWGTUZJEAQD-ZETCQYMHSA-N (D)-(+)-Pantothenic acid Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-ZETCQYMHSA-N 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- 239000000375 suspending agent Substances 0.000 claims description 3
- GHOKWGTUZJEAQD-UHFFFAOYSA-N Chick antidermatitis factor Natural products OCC(C)(C)C(O)C(=O)NCCC(O)=O GHOKWGTUZJEAQD-UHFFFAOYSA-N 0.000 claims description 2
- 235000019161 pantothenic acid Nutrition 0.000 claims description 2
- 239000011713 pantothenic acid Substances 0.000 claims description 2
- 229940055726 pantothenic acid Drugs 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 description 14
- UCSJYZPVAKXKNQ-HZYVHMACSA-N streptomycin Chemical compound CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](NC(N)=N)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]1O UCSJYZPVAKXKNQ-HZYVHMACSA-N 0.000 description 12
- WEEMDRWIKYCTQM-UHFFFAOYSA-N 2,6-dimethoxybenzenecarbothioamide Chemical compound COC1=CC=CC(OC)=C1C(N)=S WEEMDRWIKYCTQM-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 229960002385 streptomycin sulfate Drugs 0.000 description 8
- 229960005322 streptomycin Drugs 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 3
- PGBHMTALBVVCIT-VCIWKGPPSA-N framycetin Chemical compound N[C@@H]1[C@@H](O)[C@H](O)[C@H](CN)O[C@@H]1O[C@H]1[C@@H](O)[C@H](O[C@H]2[C@@H]([C@@H](N)C[C@@H](N)[C@@H]2O)O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](CN)O2)N)O[C@@H]1CO PGBHMTALBVVCIT-VCIWKGPPSA-N 0.000 description 3
- 239000000155 melt Substances 0.000 description 3
- 229940053050 neomycin sulfate Drugs 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 231100000419 toxicity Toxicity 0.000 description 3
- 230000001988 toxicity Effects 0.000 description 3
- CZWJCQXZZJHHRH-YCRXJPFRSA-N 2-[(1r,2r,3s,4r,5r,6s)-3-(diaminomethylideneamino)-4-[(2r,3r,4r,5s)-3-[(2s,3s,4s,5r,6s)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-hydroxy-4-(hydroxymethyl)-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](CO)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O CZWJCQXZZJHHRH-YCRXJPFRSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960001162 dihydrostreptomycin sulfate Drugs 0.000 description 2
- 238000004108 freeze drying Methods 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 206010029864 nystagmus Diseases 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 229950001272 viomycin Drugs 0.000 description 2
- GXFAIFRPOKBQRV-GHXCTMGLSA-N viomycin Chemical compound N1C(=O)\C(=C\NC(N)=O)NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)C[C@@H](N)CCCN)CNC(=O)[C@@H]1[C@@H]1NC(=N)N[C@@H](O)C1 GXFAIFRPOKBQRV-GHXCTMGLSA-N 0.000 description 2
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- 239000008351 acetate buffer Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 238000001962 electrophoresis Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- -1 panthenol compound Chemical class 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- QTENRWWVYAAPBI-YCRXJPFRSA-N streptomycin sulfate Chemical compound OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@@H]1[C@](C=O)(O)[C@H](C)O[C@H]1O[C@@H]1[C@@H](N=C(N)N)[C@H](O)[C@@H](N=C(N)N)[C@H](O)[C@H]1O QTENRWWVYAAPBI-YCRXJPFRSA-N 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000563 toxic property Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/22—Cyclohexane rings, substituted by nitrogen atoms
- C07H15/238—Cyclohexane rings substituted by two guanidine radicals, e.g. streptomycins
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Description
Verfahren zur Herstellung von wenig toxischen Salzen von basischen Streptomycesantibiotika Gegenstand der Patente 951 567 und 954 874 ist ein Verfahren zur Verminderung der Toxizität basischer, von Streptomycesarten erzeugter Antibiotika, bei dem die basischen Streptomycesantibiotika mit Pantothensäure oder deren Derivaten in Gegenwart eines Lösungs- oder Suspensionsmittels in bekannter Weise umgesetzt werden. In der deutschen Auslegeschrift C 11008 IVb/12 o wurde gezeigt, daß auch das Leucin befähigt ist, eine Verminderung der toxischen Eigenschaften der basischen Streptomycesantibiotika herbeizuführen, ohne daß deren antibiotische Wirksamkeit herabgesetzt wird.Process for the production of less toxic salts of basic Streptomyces Antibiotics The subject of patents 951 567 and 954 874 is a method to reduce the toxicity of basic antibiotics produced by Streptomyces species, in which the basic Streptomyces antibiotics with pantothenic acid or its derivatives reacted in the presence of a solvent or suspending agent in a known manner will. In the German Auslegeschrift C 11008 IVb / 12 o it was shown that also the leucine is capable of reducing the toxic properties of the basic Induce streptomyces antibiotics without affecting their antibiotic effectiveness is reduced.
In weiterer Bearbeitung der Aufgabenstellung, basische Streptomycesantibiotika zu entgiften, wurde nunmehr gefunden, daß das Panthenol befähigt ist, mit basischen Streptomycesantibiotika neue Komplexverbindungen zu bilden, in denen die Toxizität der basischen Streptomycesantibiotika ebenfalls stark herabgesetzt ist.In further processing of the task, basic Streptomyces antibiotics to detoxify, it has now been found that panthenol is capable of with basic Streptomyces antibiotics form new complex compounds in which the toxicity the basic Streptomyces antibiotics is also greatly reduced.
Die Bildung der Komplexverbindungen ergibt sich aus folgenden Feststellungen: Läßt man 1 Mol Streptomycin als Sulfat mit 1 Mol Panthenol in wäßriger Lösung reagieren und behandelt das Reaktionsgemisch mit Alkohol, so wird eine kristallisierte Verbindung erhalten. In der Mutterlauge von diesem kristallisierten Produkt ist kein Panthenol nachweisbar. Auch wenn man die erhaltene Komplexverbindung mehrfach mit Alkohol behandelt, läßt sich daraus kein Panthenol isolieren, obwohl Panthenol leicht in Alkohol löslich ist. Setzt man dagegen mehr als 1 Mol Panthenol mit 1 Mol Streptomycin (als Sulfat) um, so kann die 1 12o1 übersteigende Menge Panthenol aus der Mutterlauge der kristallisierten Komplexverbindung zurückgewonnen werden.The formation of the complex compounds results from the following findings: If 1 mole of streptomycin is allowed to react as sulfate with 1 mole of panthenol in aqueous solution and treating the reaction mixture with alcohol it becomes a crystallized compound obtain. There is no panthenol in the mother liquor of this crystallized product verifiable. Even if the complex compound obtained is repeatedly treated with alcohol treated, no panthenol can be isolated from it, although panthenol can easily be converted into Alcohol is soluble. If, on the other hand, more than 1 mole of panthenol is used with 1 mole of streptomycin (as sulfate), the amount of panthenol in excess of 1 12o1 can be extracted from the mother liquor the crystallized complex compound can be recovered.
Vergleicht man das Verhalten von Streptomycinsulfat mit dem der Streptomycinsulfatpanthenolkomplexverbindung
im elektrischen Feld (Papierelektrophorese), so ergibt sich, daß die Wanderungsgeschwindigkeit
des Streptomycins in der Komplexverbindung gegenüber der des Streptomycins in dem
Salz deutlich herabgesetzt ist. Es wurden bei einer Spannung von 100V und bei Verwendung
eines Acetatpuffers vom pH = 5,0 folgende Werte erhalten:
Die Herstellung der neuen Verbindungen kann in Gegenwart oder auch in Abwesenheit eines Lösungs- oder Suspensionsmittels erfolgen. Beispiel 1 12,5 g Streptomycinsulfat werden in 50 cm3 Wasser gelöst und dann unter Rühren tropfenweise mit einer Lösung von 3,3 g Panthenol in 25 cm' Wasser versetzt. Das Reaktionsgemisch wird im Vakuum bei einer Radtemperatur von 45 bis 50° bis zur Sirupkonsistenz eingedampft. Der Rückstand wird mit Äthanol durchgerührt, wobei er kristallin wird. Die erhaltene kristalline Verbindung aus Panthenol und Streptomycinsulfat schmilzt bei 166° unter Zersetzung. Sie ist löslich in Wasser, unlöslich in den meisten der gebräuchlichen organischen Lösungsmittel.The preparation of the new compounds can be in the presence or else take place in the absence of a solvent or suspending agent. Example 1 12.5 g streptomycin sulfate are dissolved in 50 cm3 of water and then dropwise with stirring mixed with a solution of 3.3 g of panthenol in 25 cm 'of water. The reaction mixture is evaporated to a syrup consistency in a vacuum at a wheel temperature of 45 to 50 °. The residue is stirred with ethanol, whereupon it becomes crystalline. The received crystalline compound of panthenol and streptomycin sulfate melts below at 166 ° Decomposition. It is soluble in water, insoluble in most of the common ones organic solvents.
Beispiel 2 Man verfährt wie im Beispiel 1, dampft jedoch das Reaktionsgemisch nicht ein, sondern versetzt die wäßrige Lösung mit 250 cm' Äthanol. Nach einiger Zeit kristallisiert das Reaktionsprodukt, vor allem, wenn man die Lösung im Eisschrank aufbewahrt, aus. Schmelzpunkt: 166 bis 168° unter Zersetzung. " Beispiel 3 7,6:g Streptomycinsulfat yverden einigeZeit-kräftig mit-2 g Panthenol verrieben, wobei nach- und nach das Panthenol aufgenommen wird. Das erhaltene Produkt schmilzt bei 165 bis 168° unter Zersetzung.EXAMPLE 2 The procedure is as in Example 1, except that the reaction mixture is not evaporated, but rather 250 cm of ethanol are added to the aqueous solution. After some time, the reaction product crystallizes out, especially if the solution is kept in the refrigerator. Melting point: 166 to 168 ° with decomposition. Example 3 7.6: g of streptomycin sulfate are triturated vigorously for some time with 2 g of panthenol, the panthenol being gradually absorbed. The product obtained melts at 165 to 168 ° with decomposition.
Beispiel 4 12,5g Dihydrostreptomycinsulfat werden in 50 cm3 Wasser gelöst und unter Rühren tropfenweise mit einer Lösung von 3,3 g Panthenol in 25 cm3 Wasser versetzt. Das Reaktionsgemisch wird dann der Gefriertrocknung unterworfen. Man erhält die Verbindung aus Dihydrostreptomycinsulfat und Panthenol als ein in Wasser leichtlösliches Produkt, das sich bei 185 bis 188° braun färbt und bei 232° verkohlt.Example 4 12.5 g of dihydrostreptomycin sulfate are dissolved in 50 cm3 of water dissolved and with stirring dropwise with a solution of 3.3 g panthenol in 25 cm3 of water added. The reaction mixture is then subjected to freeze drying. The compound of dihydrostreptomycin sulfate and panthenol is obtained as an in Easily soluble product in water, which turns brown at 185 to 188 ° and at 232 ° charred.
Beispiels Man verfährt wie im Beispiel 4, jedoch unter Verwendung von 12g Viomycinsulfat und 3,82g Panthenol. Nach der Gefriertrocknung erhält man die Verbindung aus. Viomycinsulfat und Panthenol, die bei 242° unter Zersetzung schmilzt.Example The procedure is as in Example 4, but using of 12g viomycin sulfate and 3.82g panthenol. After freeze-drying, one obtains the connection off. Viomycin sulfate and panthenol, which decompose at 242 ° melts.
Beispiel 6 Man verfährt wie im Beispiel 4, jedoch unter Verwendung. von 11,56 g Neomycinsulfat und 2,05 g Panthenol. Man erhält die Verbindung aus Neomycinsulfat und Panthenol, die sich ab 160° braun färbt und bei 190° verkohlt. Diese Verbindung ist sehr leicht löslich in Wasser, unlöslich in Alkohol.Example 6 The procedure is as in Example 4, but using. of 11.56 g neomycin sulfate and 2.05 g panthenol. The compound is obtained from neomycin sulfate and panthenol, which turns brown from 160 ° and charred at 190 °. This connection is very easily soluble in water, insoluble in alcohol.
Das als Ausgangsmaterial benutzte Neomycinsulfat beginnt ab 190° zu schmelzen und zersetzt sich langsam bei 235 bis 250°.The neomycin sulfate used as the starting material begins to increase from 190 ° melt and decompose slowly at 235 to 250 °.
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC12428A DE1011880B (en) | 1956-01-18 | 1956-01-18 | Process for the production of low-toxicity salts of basic Streptomyces antibiotics |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEC12428A DE1011880B (en) | 1956-01-18 | 1956-01-18 | Process for the production of low-toxicity salts of basic Streptomyces antibiotics |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1011880B true DE1011880B (en) | 1957-07-11 |
Family
ID=7015207
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC12428A Pending DE1011880B (en) | 1956-01-18 | 1956-01-18 | Process for the production of low-toxicity salts of basic Streptomyces antibiotics |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE1011880B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1043325B (en) | 1956-03-29 | 1958-11-13 | Lepetit Spa | Process for the production of less toxic calcium glucoheptonate complex salts of streptomycin and dihydrostreptomycin |
| DE1104502B (en) * | 1959-12-11 | 1961-04-13 | Bayer Ag | Process for the production of a streptomycin compound which is sparingly soluble in water and has a protahed streptomycin effect |
-
1956
- 1956-01-18 DE DEC12428A patent/DE1011880B/en active Pending
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1043325B (en) | 1956-03-29 | 1958-11-13 | Lepetit Spa | Process for the production of less toxic calcium glucoheptonate complex salts of streptomycin and dihydrostreptomycin |
| DE1104502B (en) * | 1959-12-11 | 1961-04-13 | Bayer Ag | Process for the production of a streptomycin compound which is sparingly soluble in water and has a protahed streptomycin effect |
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