PL77B1 - Method for the production of digitalis foxicides from digitalis glycosides. - Google Patents
Method for the production of digitalis foxicides from digitalis glycosides. Download PDFInfo
- Publication number
- PL77B1 PL77B1 PL77A PL7719A PL77B1 PL 77 B1 PL77 B1 PL 77B1 PL 77 A PL77 A PL 77A PL 7719 A PL7719 A PL 7719A PL 77 B1 PL77 B1 PL 77B1
- Authority
- PL
- Poland
- Prior art keywords
- digitalis
- glycosides
- production
- foxicides
- alcohol
- Prior art date
Links
- 241000208011 Digitalis Species 0.000 title claims description 6
- 229940082657 digitalis glycosides Drugs 0.000 title claims description 6
- 238000000034 method Methods 0.000 title claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 238000010790 dilution Methods 0.000 claims description 3
- 239000012895 dilution Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 229930182470 glycoside Natural products 0.000 description 3
- 150000002338 glycosides Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000004480 active ingredient Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- LRBQNJMCXXYXIU-NRMVVENXSA-N tannic acid Chemical class OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-NRMVVENXSA-N 0.000 description 2
- 229920001864 tannin Polymers 0.000 description 2
- 239000001648 tannin Substances 0.000 description 2
- APSWDBKJUOEMOA-MTEWDWANSA-N (2S)-4-amino-2-[[(2S,3S)-2-[[(2S)-2-[[(2S)-2-[[(2S,3R)-2-[[(2S,3S)-2-[(2-aminoacetyl)amino]-3-methylpentanoyl]amino]-3-hydroxybutanoyl]amino]propanoyl]amino]-4-methylpentanoyl]amino]-3-methylpentanoyl]amino]-4-oxobutanoic acid Chemical compound CC[C@H](C)[C@H](NC(=O)CN)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(O)=O APSWDBKJUOEMOA-MTEWDWANSA-N 0.000 description 1
- TUSDEZXZIZRFGC-UHFFFAOYSA-N 1-O-galloyl-3,6-(R)-HHDP-beta-D-glucose Natural products OC1C(O2)COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC1C(O)C2OC(=O)C1=CC(O)=C(O)C(O)=C1 TUSDEZXZIZRFGC-UHFFFAOYSA-N 0.000 description 1
- WDJUZGPOPHTGOT-OAXVISGBSA-N Digitoxin Natural products O([C@H]1[C@@H](C)O[C@@H](O[C@@H]2C[C@@H]3[C@@](C)([C@@H]4[C@H]([C@]5(O)[C@@](C)([C@H](C6=CC(=O)OC6)CC5)CC4)CC3)CC2)C[C@H]1O)[C@H]1O[C@@H](C)[C@H](O[C@H]2O[C@@H](C)[C@@H](O)[C@@H](O)C2)[C@@H](O)C1 WDJUZGPOPHTGOT-OAXVISGBSA-N 0.000 description 1
- 239000001263 FEMA 3042 Substances 0.000 description 1
- LRBQNJMCXXYXIU-PPKXGCFTSA-N Penta-digallate-beta-D-glucose Natural products OC1=C(O)C(O)=CC(C(=O)OC=2C(=C(O)C=C(C=2)C(=O)OC[C@@H]2[C@H]([C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)[C@H](OC(=O)C=3C=C(OC(=O)C=4C=C(O)C(O)=C(O)C=4)C(O)=C(O)C=3)O2)OC(=O)C=2C=C(OC(=O)C=3C=C(O)C(O)=C(O)C=3)C(O)=C(O)C=2)O)=C1 LRBQNJMCXXYXIU-PPKXGCFTSA-N 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 229960000648 digitoxin Drugs 0.000 description 1
- WDJUZGPOPHTGOT-XUDUSOBPSA-N digitoxin Chemical compound C1[C@H](O)[C@H](O)[C@@H](C)O[C@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)CC5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O WDJUZGPOPHTGOT-XUDUSOBPSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- -1 dry Substances 0.000 description 1
- 229940118313 gitalin Drugs 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 description 1
- 239000011973 solid acid Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 229940033123 tannic acid Drugs 0.000 description 1
- 235000015523 tannic acid Nutrition 0.000 description 1
- 229920002258 tannic acid Polymers 0.000 description 1
- 235000018553 tannin Nutrition 0.000 description 1
Description
Gottlieb i Tambach (Munch. Med. Wo- chenschrift 1911 Nr. 1) wykazali, ze czyn¬ ne skladniki naparstnicy zawarte sa w tym surowcu w postaci digitoglyko- tannoidów. Wyodrebnione z nich zwiaz¬ ki sa prawie nierozpuszczalne w wrodzie i rozcienczonych kwasach, natomiast la¬ two rozpuszczalne w alkoholu i alkaljach.Potem ustalonem zostalo, iz te digito- glykotannoidy moga byc wytwarzane ze swoich czesci skladowych.Dalej wykryto, iz mozna otrzymac po¬ laczenia miedzy zwiazkami kwasów garb¬ nikowych i czynnemi glykozydami w in¬ nych dowolnych stosunkach. Dzieki te¬ mu niema juz zadnego znaczenia zmien¬ na zawartosc czynnych skladników w su¬ rowcu, zalezna zazwyczaj od miejsca, pory roku i t. p. Wobec tego lecznictwo uzyskalo preparaty zawsze jednolite pod wzgledem chemicznym, które dzieki trud¬ nej rozpuszczalnosci w rozcienczonych kwasach nie dzialaja na zoladek, a przez latwe rozpuszczanie w alkaljach podlega¬ ja zupelnemu wchlonieciu w jelitach.Pozatem, dzieki swej rozpuszczalnosci równiez w bardzo slabych alkaljach, nadaja sie one wyjatkowo dobrze do wstrzykiwan.Przyklad I.Alkaliczno-wodny rozczyn natural¬ nych znajdujacych sie w naparstnicy di- gitannoidów nasycamy chloroformem, do którego dodano nieco alkoholu, alkoho¬ lu metylowego lub podobnie dzialaja¬ cych rozpuszczalników, poczem rozpu¬ szczalnik sie oddestylowuje; 100 g otrzy¬ mane w ten sposób mieszaniny glyko¬ zydów rozpuszczamy w 500 cm3 alkoho-lu. Ten rozczyn traktujemy alkoholo¬ wym rozczynem 300 g zwiazków kwa- sogarbnikowych, otrzymanych znanym sposobem z naparstnicy, poczem wysu¬ szamy przez sprasowanie. Sproszkowa¬ na i przesiana pozostalosc przedstawia sie w postaci szaro-brunatnego proszku, nierozpuszczalnego w wodzie i slabych kwasach, rozpuszczalnego w alkoholu i bardzo latwo w alkaljach.Przyklad II. 100 g t. zw. analitycznej digitaliny t. zn. cala zawartosc rozpuszczonych w chloroformie glykozydów naparstnicy rozpuszczamy w 500 cm3 alkoholu; po- zatem postepuje sie jak w przykladzie I.Otrzymujemy szaro - brunatny proszek, prawie nierozpuszczalny w wodzie i sla¬ bych kwasach, lepiej w alkoholu i zu¬ pelnie dobrze w alkaljach. Zawiera 25% analitycznej digit*oxiny.Przyklad III. 100 g digitoxiny rozpuszczamy w 500 cm8 wyskoku i traktujemy wyskokowym rozczynem 300 g kwasów naparstnico- wo-garbnikowych, suszymy, proszkuje¬ my i.przesiewamy. Otrzymujemy szaro¬ brunatny proszek, prawie nierozpu¬ szczalny w wodzie i stalych kwasach, lepiej w alkoholu i zupelnie latwo w al¬ kaljach.Przyklad IV. 100 g gitaliny (t. j. rozpuszczalna w wodzie czesc glykozydów naparstnicy) rozpuszczamy w 500 cm3 wyskoku; roz¬ czyn ten traktujemy rozczynem 300 g kwasów garbnikowych naparstnicy, po¬ czem wysuszamy. Pozostalosc proszku¬ jemy i przesiewamy. Otrzymujemy sza¬ ro- brunatny proszek nierozpuszczalny w wodzie i slabych kwasach, lepiej w al¬ koholu, a zupelnie dobrze w alkaljach.W przytoczonych wyzej przykladach moga byc uzyte dowolne mieszaniny wyodrebnionych znanym sposobem czyn¬ nych glykozydów i kwasów garbnikowo- naparstnicowych.W taki sposób mozna otrzymywac scisle jednolite pod wzgledem chemicz¬ nym przetwory, albowiem sklad ich jest scisle znany, dzieki czemu za;biegi lecz¬ nicze zyskuja na dokladnosci i pew¬ nosci. Pozatem dzieki rozpuszczalnosci tych preparatów w slabych alkaljach mozna przyrzadzac naprz. do wstrzyki¬ wac wsródzylnych rozczyny o tak znacz- nem stezeniu, jakiego dotychczas nie dalo sie osiagnac z zadnym innym przetworem, za wyjatkiem naturalnych digitonoidów. PL PLGottlieb and Tambach (Munch. Med. Wochenschrift 1911 No. 1) showed that the active ingredients of digitalis are contained in this raw material in the form of digitoglycoatnoids. The compounds isolated therefrom are almost insoluble in nature and dilute acids, while the lacquer is soluble in alcohol and alkali. It was later determined that these digitoglottosides could be produced from their constituent parts. Further it was found that it was possible to obtain combinations of tannic acid compounds and active glycosides in any other ratio. Due to this, the change in the content of active ingredients in the raw material, usually depending on the place, season, etc., is of no importance. Therefore, the treatment has obtained preparations that are always chemically uniform, which due to the difficult solubility in dilute acids do not work. on the stomach, and due to easy dissolution in alkalis it is completely absorbed in the intestines. Then, due to their solubility also in very weak alkalines, they are exceptionally well suited for injection. Example I. Alkaline-water solution of natural substances found in digitalis We saturate the digitanids with chloroform, to which some alcohol, methyl alcohol or similar solvents have been added, and then the solvent is distilled off; Dissolve 100 g of the mixture of glycosides obtained in this way in 500 cm 3 of alcohol. We treat this dilution with an alcoholic solution of 300 g of acid tarbate compounds, obtained in a known manner from digitalis, and then dry by pressing. The powdered and sieved residue appears as a gray-brown powder, insoluble in water and weak acids, soluble in alcohol and very easily in alkalis. Example II. 100 g t. analytical digitalina, vol. Dissolve the entire content of digitalis glycosides dissolved in chloroform in 500 cm3 of alcohol; the procedure is therefore as in Example 1. We obtain a gray-brown powder, almost insoluble in water and weak acids, better in alcohol and quite well in alkalis. Contains 25% of analytical digit * oxin. Example III. Dissolve 100 g of digitoxin in a 500 cm3 spike and treat 300 g of digitalic-tannin acids with a blast solution, dry, powder and sieve. We obtain a gray-brown powder, almost insoluble in water and solid acids, preferably in alcohol and quite easily in alkali. Dissolve 100 g of gitalin (i.e. the water-soluble part of digitalis glycosides) in 500 cm3 of the jump; We treat this solution with a dilution of 300 g of digitalis tannic acid and then dry it. Powder the rest and sieve. We obtain a gray-brown powder, insoluble in water and weak acids, preferably in alcohol, and perfectly well in alkalis. In the above-mentioned examples, any mixtures of active glycosides and tannins, isolated by a known method, can be used. This method can be used to obtain strictly homogeneous preparations, since their composition is strictly known, so that the treatment processes are more accurate and reliable. Moreover, thanks to the solubility of these preparations in weak alkalis, it is possible to prepare, for example, for injecting intra-human solutions of such a high concentration that has not been achieved so far with any other preparation, except for natural digitonoids. PL PL
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Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL77B1 true PL77B1 (en) | 1924-05-26 |
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