DE644078C - Process for the preparation of a salt of 4-oxy-3-acetylaminophenyl-1-arsic acid with the toxin of iso-octylhydrocupreine (vuzinotoxin) - Google Patents
Process for the preparation of a salt of 4-oxy-3-acetylaminophenyl-1-arsic acid with the toxin of iso-octylhydrocupreine (vuzinotoxin)Info
- Publication number
- DE644078C DE644078C DES120839D DES0120839D DE644078C DE 644078 C DE644078 C DE 644078C DE S120839 D DES120839 D DE S120839D DE S0120839 D DES0120839 D DE S0120839D DE 644078 C DE644078 C DE 644078C
- Authority
- DE
- Germany
- Prior art keywords
- salt
- acetylaminophenyl
- oxy
- vuzinotoxin
- octylhydrocupreine
- 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
Links
- 150000003839 salts Chemical class 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- DIOGDSVVUWNLHM-UHFFFAOYSA-N (5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)-[6-(6-methylheptoxy)quinolin-4-yl]methanol Chemical compound C1=C(OCCCCCC(C)C)C=C2C(C(O)C3CC4CCN3CC4CC)=CC=NC2=C1 DIOGDSVVUWNLHM-UHFFFAOYSA-N 0.000 title claims description 3
- 239000002253 acid Substances 0.000 title claims description 3
- 238000002360 preparation method Methods 0.000 title claims description 3
- 239000003053 toxin Substances 0.000 title claims description 3
- 231100000765 toxin Toxicity 0.000 title claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229930013930 alkaloid Natural products 0.000 description 2
- 229940000488 arsenic acid Drugs 0.000 description 2
- LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- DJHGAFSJWGLOIV-UHFFFAOYSA-N Arsenic acid Chemical compound O[As](O)(O)=O DJHGAFSJWGLOIV-UHFFFAOYSA-N 0.000 description 1
- 235000001258 Cinchona calisaya Nutrition 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- RSPISYXLHRIGJD-UHFFFAOYSA-N OOOO Chemical compound OOOO RSPISYXLHRIGJD-UHFFFAOYSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- VJWWIRSVNSXUAC-UHFFFAOYSA-N arsinic acid Chemical class O[AsH2]=O VJWWIRSVNSXUAC-UHFFFAOYSA-N 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- KMPWYEUPVWOPIM-UHFFFAOYSA-N cinchonidine Natural products C1=CC=C2C(C(C3N4CCC(C(C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-UHFFFAOYSA-N 0.000 description 1
- KMPWYEUPVWOPIM-LSOMNZGLSA-N cinchonine Chemical compound C1=CC=C2C([C@@H]([C@H]3N4CC[C@H]([C@H](C4)C=C)C3)O)=CC=NC2=C1 KMPWYEUPVWOPIM-LSOMNZGLSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 229960000948 quinine Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/66—Arsenic compounds
- C07F9/70—Organo-arsenic compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Es wurde gefunden, daß man zu einem therapeutisch wertvollen Vuzinotoxinsalz gelangt, wenn man Vuzinotoxin mit 4-Öxy-3-acetylaminophenyl-i-arsinsäure nach den für die Salzbildunig· üblichen Arbeitsweisen zusammenbringt. It has been found that a therapeutically valuable vucinotoxin salt is obtained, if you have vuzinotoxin with 4-Öxy-3-acetylaminophenyl-i-arsinic acid according to the usual procedures for salt formation.
Die Herstellung des Salzes ist in den folgenden Beispielen erläutert.The preparation of the salt is illustrated in the following examples.
Beispiel ιExample ι
4,24 g Vuziniotoxin werden in 50 ecm Alkohol gelöst und 2,75 g 4-Oxy-3-acetylaminophenyl-1 -arsinsäure in die heiße Lösung eingetragen. Nach erfolgter Auflösung wird filtriert und die Lösung im Vakuum zur Trockne eingedampft.4.24 g of vuciniotoxin are in 50 ecm of alcohol dissolved and 2.75 g of 4-oxy-3-acetylaminophenyl-1 arsenic acid entered into the hot solution. After dissolution has taken place, it is filtered and the solution is reduced in vacuo Evaporated to dryness.
Statt in Alkohol kann man" die beiden Ausgangsstoffe auch in heißem Wasser lösen und die Lösung wie oben zur Trockne verdampfen. Das Salz ist leicht löslich in Alkohol und lauwarmem Wasser.Instead of alcohol you can use "the two starting materials also dissolve in hot water and evaporate the solution to dryness as above. The salt is easily soluble in alcohol and lukewarm water.
4,6g Vuzinotoxinhydrochlorid und 2,98 g 4-oxy-3-acetylami:n!ophenyl-i-arsinsaures Natrium werden in 20 ecm Wasser gelöst und die Lösung zur Trockne eingedampft. Der Rückstand wird mit absolutem Alkohol aufgenommen und vom Natriumchlorid abfiltriert. Aus der alkoholischen Lösung wird durch Einengen im Vakuum das 4-Oxy-3-acetylaminophenyl-1 -arsinsäure Toxin des iso-Octylhydrocupreins gewonnen.4.6 g of vuzinotoxin hydrochloride and 2.98 g of 4-oxy-3-acetylami : n! Ophenyl-i-arsinic acid sodium are dissolved in 20 ecm of water and the solution is evaporated to dryness. The residue is taken up with absolute alcohol and the sodium chloride is filtered off. The 4-oxy-3-acetylaminophenyl-1-arsenic acid toxin of iso-octylhydrocupreine is obtained from the alcoholic solution by concentration in vacuo.
Das neue Salz soll in der. Therapie Verwendung finden; es zeichnet sich durch stark bakterieide Eigenschaften aus. So werden z. B. Streptokokken in einer Verdünnung von 1AoOOOO schon in 5 Minuten abgetötet. Es besitzt demnach eine größere Wirkung als das nach dem Verfahren der Patentschrift 621 198, Klasse J2p, dargestellte kampfersaure Vuzinatoxin, das nach den Angaben der Patentschrift in einer Verdünnung 1A1OOOO auf Streptokokken abtötend wirkt.The new salt should be in the. Therapy use; it is characterized by strong bacterial properties. So z. B. Streptococci killed in a dilution of 1 AOOOO in 5 minutes. Therefore it has a greater effect than obtained by the method of the patent specification 621198, class J2P, shown camphor acid Vuzinatoxin, the au f according to the information of the specification in a dilution 1 A 1 OOOO streptococci acts abtötend.
Bekannt sind zwar schon Salze der Chinaalkaloide mit organischen Arsinsäuren (Patentschrift 495256, Klasse 12 p). Es handelt sich aber hier um Substanzen, die gegen Malariaparasiten spezifisch wirken sollen. Die Alkaloide Chinin und Cinchonin selbst besitzen z. B. Streptokokken gegenüber nur eine ganz schwache Wirkung.Salts of the china alkaloids with organic arsinic acids are already known (patent specification 495256, class 12 p). But these are substances that act against Malaria parasites should have a specific effect. Possess the alkaloids quinine and cinchonine themselves z. B. against streptococci only a very weak effect.
Claims (1)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DES120839D DE644078C (en) | 1935-12-15 | 1935-12-15 | Process for the preparation of a salt of 4-oxy-3-acetylaminophenyl-1-arsic acid with the toxin of iso-octylhydrocupreine (vuzinotoxin) |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DES120839D DE644078C (en) | 1935-12-15 | 1935-12-15 | Process for the preparation of a salt of 4-oxy-3-acetylaminophenyl-1-arsic acid with the toxin of iso-octylhydrocupreine (vuzinotoxin) |
Publications (1)
Publication Number | Publication Date |
---|---|
DE644078C true DE644078C (en) | 1937-05-25 |
Family
ID=7535346
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DES120839D Expired DE644078C (en) | 1935-12-15 | 1935-12-15 | Process for the preparation of a salt of 4-oxy-3-acetylaminophenyl-1-arsic acid with the toxin of iso-octylhydrocupreine (vuzinotoxin) |
Country Status (1)
Country | Link |
---|---|
DE (1) | DE644078C (en) |
-
1935
- 1935-12-15 DE DES120839D patent/DE644078C/en not_active Expired
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE644078C (en) | Process for the preparation of a salt of 4-oxy-3-acetylaminophenyl-1-arsic acid with the toxin of iso-octylhydrocupreine (vuzinotoxin) | |
DE753235C (en) | Process for the production of aqueous lactoflavin solutions | |
DE675817C (en) | Process for the preparation of readily water-soluble salts of diarylaminoalkylcarbinoln | |
DE691339C (en) | Process for the preparation of concentrated aqueous theophylline solutions | |
DE690488C (en) | Process for the production of concentrated aqueous caffeine solutions | |
DE677152C (en) | Process for the production of aqueous quinidine salt solutions | |
DE637792C (en) | Process for the production of durable solutions of complex lead salts | |
DE585519C (en) | Process for the preparation of organic bismuth compounds | |
DE1517751C3 (en) | Method for preventing the formation of flaky lysozyme and / or lysozyme salt precipitates in aqueous solutions containing lysozyme and / or lysozyme salts | |
DE434264C (en) | Method for the preparation of a therapeutically effective preparation from digitalis sheets | |
DE636308C (en) | Process for the production of praseodymium salts or their aqueous solutions | |
AT52848B (en) | Process for the production of preparations for diagnostic and curative purposes from pure cultures of the pathogens recognized as specific for the individual disease. | |
DE571404C (en) | Process for removing proteins from liquids, e.g. B. Sera | |
DE220862C (en) | ||
DE676436C (en) | Process for the preparation of aqueous solutions of p-aminobenzene sulfonamide | |
DE682875C (en) | Process for the production of stable organic ferrous compounds | |
AT159318B (en) | Process for the preparation of readily water-soluble compounds of dialkylaminoalkyldiarylcarbinols. | |
AT81074B (en) | Process for the preparation of a water-soluble, iVerfahren for the preparation of a water-soluble, injectable preparation from opium, the total alkaline injectable preparation from opium, the total alkaloids in their natural binding and mixture oids in their natural binding and mixing respectively. Containing quantitative proportions. respectively Containing quantitative proportions. | |
DE942534C (en) | Process for the production of durable and highly effective solutions or suspensions of antibiotic agents | |
DE203081C (en) | ||
DE337939C (en) | Process for the production of a betaine of hexamethylenetetramine | |
DE384688C (en) | Process for the preparation of durable guaiacol preparations in aqueous solution | |
DE646706C (en) | Process for the preparation of substituted 6, 7-dioxy-1, 2, 3, 4-tetrahydroisoquinoline-1-carboxylic acids | |
AT157797B (en) | Process for the preparation of aqueous quinidine salt solutions. | |
DE404697C (en) | Process for the production of lithium naphthenic acid |