CH176255A - Process for the preparation of a new cardiac active glucoside. - Google Patents
Process for the preparation of a new cardiac active glucoside.Info
- Publication number
- CH176255A CH176255A CH176255DA CH176255A CH 176255 A CH176255 A CH 176255A CH 176255D A CH176255D A CH 176255DA CH 176255 A CH176255 A CH 176255A
- Authority
- CH
- Switzerland
- Prior art keywords
- glucoside
- preparation
- parts
- new
- methanol
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 7
- 229930182478 glucoside Natural products 0.000 title claims description 6
- 150000008131 glucosides Chemical class 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 3
- 230000000747 cardiac effect Effects 0.000 title description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
- 239000008103 glucose Substances 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- SHIBSTMRCDJXLN-UHFFFAOYSA-N Digoxigenin Natural products C1CC(C2C(C3(C)CCC(O)CC3CC2)CC2O)(O)C2(C)C1C1=CC(=O)OC1 SHIBSTMRCDJXLN-UHFFFAOYSA-N 0.000 claims description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 2
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 claims description 2
- 229910001861 calcium hydroxide Inorganic materials 0.000 claims description 2
- 239000000920 calcium hydroxide Substances 0.000 claims description 2
- QONQRTHLHBTMGP-UHFFFAOYSA-N digitoxigenin Natural products CC12CCC(C3(CCC(O)CC3CC3)C)C3C11OC1CC2C1=CC(=O)OC1 QONQRTHLHBTMGP-UHFFFAOYSA-N 0.000 claims description 2
- SHIBSTMRCDJXLN-KCZCNTNESA-N digoxigenin Chemical compound C1([C@@H]2[C@@]3([C@@](CC2)(O)[C@H]2[C@@H]([C@@]4(C)CC[C@H](O)C[C@H]4CC2)C[C@H]3O)C)=CC(=O)OC1 SHIBSTMRCDJXLN-KCZCNTNESA-N 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
- 241000208011 Digitalis Species 0.000 claims 1
- FDWRIIDFYSUTDP-KVTDHHQDSA-N (2r,4r,5s,6r)-6-methyloxane-2,4,5-triol Chemical compound C[C@H]1O[C@@H](O)C[C@@H](O)[C@@H]1O FDWRIIDFYSUTDP-KVTDHHQDSA-N 0.000 description 3
- FDWRIIDFYSUTDP-UHFFFAOYSA-N 102850-49-7 Natural products CC1OC(O)CC(O)C1O FDWRIIDFYSUTDP-UHFFFAOYSA-N 0.000 description 3
- JWFRNGYBHLBCMB-UHFFFAOYSA-N D-Canaytose Natural products CC(O)C(O)C(O)CC=O JWFRNGYBHLBCMB-UHFFFAOYSA-N 0.000 description 3
- 240000001879 Digitalis lutea Species 0.000 description 2
- LTMHDMANZUZIPE-AMTYYWEZSA-N Digoxin 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](O)C4)[C@H](C4=CC(=O)OC4)CC5)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 LTMHDMANZUZIPE-AMTYYWEZSA-N 0.000 description 2
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- LTMHDMANZUZIPE-PUGKRICDSA-N digoxin 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)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O LTMHDMANZUZIPE-PUGKRICDSA-N 0.000 description 2
- 229960005156 digoxin Drugs 0.000 description 2
- LTMHDMANZUZIPE-UHFFFAOYSA-N digoxine Natural products C1C(O)C(O)C(C)OC1OC1C(C)OC(OC2C(OC(OC3CC4C(C5C(C6(CCC(C6(C)C(O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)CC2O)C)CC1O LTMHDMANZUZIPE-UHFFFAOYSA-N 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 150000002016 disaccharides Chemical class 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 230000007071 enzymatic hydrolysis Effects 0.000 description 1
- 238000006047 enzymatic hydrolysis reaction Methods 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J19/00—Normal steroids containing carbon, hydrogen, halogen or oxygen, substituted in position 17 by a lactone ring
- C07J19/005—Glycosides
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Verfahren zur Darstellung eines neuen herzwirksamen Glucosides. Das vorliegende Verfahren betrifft die Dar stellung eines neuen herzwirksamen Gluco- sides, welches dadurch gekennzeichnet ist, dass man das nach dem Verfahren des Patentes Nr. 167650 erhältliche genuine Digitalis Lanataglucosid C in Gegenwart von Wasser mit Calciumhydroxyd behandelt.
<I>Beispiel:</I> 2,2 gr Lanataglucosid C (lufttrocken), dar gestellt nach dem in derPatentschriftNr.167650 beschriebenen Verfahren, werden in 47 em0 Methanol gelöst. Zu dieser Lösung werden 47 cms einer Kalklösung vom Titer
EMI0001.0012
hinzugefügt. Das Gemisch wird verschlossen über Nacht bei Zimmertemperatur stehen ge lassen, wobei die alkalische Reaktion ver schwindet und ein Teil des Reaktionsproduktes sich in amorpher Form ausscheidet. Beim Auf nehmen des Reaktionsproduktes mit heissem Methylalkohol und Erkalten scheidet sich das acylfreie Produkt als weisses, kristallinisches Pulver aus.
Das so erhaltene desacetylierte Lanata- glucosid C kristallisiert aus 75 %igem Alkohol oder 75 %igem Methanol in rhombenförmigen Täfelchen. 1 Teil davon löst sich bei gewöhn licher Temperatur in 200 Teilen Methanol, ca. 2500 Teilen Äthanol, in ca. 6000 Teilen Wasser. In Äther ist es unlöslich.
Die Ele mentaranalyse ergab: C - 59,1 bis<B>69,8</B> % und H = 7,7 bis 8,1%. Bei der Laktontitra- tion verbrauchten 0,269 gr der Substanz 2,8 em3 1/1o n Lauge, woraus sich ein Mole kulargewicht von ca. 960 ableitet.
Das spezi fische, optische Drehungsvermögen beträgt a 'D' = +12 0. C =1,084 in 75 %igem Alkohol. Bei vorsichtiger Hydrolyse mit verdünnten Säuren erhält man ca.
410/0 Aglucon (Digogi- genin), ca. 31% Digitoxose und ca. 32 0% eines gut kristallisierten Disaccharides C12H2200, welches bei energischerer Hydrolyse in Digit- oxose und Glucose gespalten wird nach der Gleichung:
<B>C12H2209</B> + 1E120 =<B>C6H1204</B> -+- C6111206. Das neue Glucosid wird also bei der vollständigen sauren Hydrolyse nach der Gleichurig C471174019 + <B>4</B>11<B>20</B> = <B>C23118406</B> + 3C6111204 -+- C6111206 Digoxigenin Digitoxose Glucose gespalten.
Bei der Einwirkung eines in den Blättern der Digitalis purpurea enthaltenen Enzyms erfolgt eine enzymatische Hydrolyse, wobei Digoxin und Glucose gebildet werden nach der Gleichung: C471174019 -+" H20 =<B>C411164014</B> -+- C6111206 Digoxin Glucose Das neue Glucosid soll in der Therapie Verwendung finden.
Process for the preparation of a new cardiac active glucoside. The present method relates to the production of a new cardiac glucoside, which is characterized in that the genuine digitalis lanataglucoside C obtainable by the method of patent no. 167650 is treated with calcium hydroxide in the presence of water.
<I> Example: </I> 2.2 gr Lanataglucosid C (air-dry), prepared according to the process described in patent specification 167650, are dissolved in 47 em0 methanol. To this solution 47 cms of a lime solution of the titer
EMI0001.0012
added. The mixture is closed and left to stand overnight at room temperature, the alkaline reaction disappearing and part of the reaction product separating out in amorphous form. When taking the reaction product with hot methyl alcohol and cooling it, the acyl-free product separates out as a white, crystalline powder.
The deacetylated Lanataglucoside C obtained in this way crystallizes from 75% alcohol or 75% methanol in diamond-shaped tablets. 1 part of it dissolves at the usual temperature in 200 parts of methanol, about 2500 parts of ethanol, in about 6000 parts of water. It is insoluble in ether.
The elemental analysis showed: C - 59.1 to 69.8% and H = 7.7 to 8.1%. During lactone titration, 0.269 gram of the substance consumed 2.8 em3 1 / 1o n lye, from which a molecular weight of approx.
The specific optical rotatability is a 'D' = +12 0. C = 1.084 in 75% alcohol. Careful hydrolysis with dilute acids gives approx.
410/0 aglucon (digoggenin), approx. 31% digitoxose and approx. 32 0% of a well crystallized disaccharide C12H2200, which is split into digitoxose and glucose with more vigorous hydrolysis according to the equation:
<B> C12H2209 </B> + 1E120 = <B> C6H1204 </B> - + - C6111206. The new glucoside becomes so during the complete acid hydrolysis according to the equation C471174019 + <B> 4 </B> 11 <B> 20 </B> = <B> C23118406 </B> + 3C6111204 - + - C6111206 digoxigenin digitoxose glucose split.
When an enzyme contained in the leaves of Digitalis purpurea acts, enzymatic hydrolysis takes place, with digoxin and glucose being formed according to the equation: C471174019 - + "H20 = <B> C411164014 </B> - + - C6111206 Digoxin glucose The new glucoside should be used in therapy.
Claims (1)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH176255T | 1932-07-22 | ||
| CH171174T | 1932-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH176255A true CH176255A (en) | 1935-03-31 |
Family
ID=25719025
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH176255D CH176255A (en) | 1932-07-22 | 1932-07-22 | Process for the preparation of a new cardiac active glucoside. |
Country Status (1)
| Country | Link |
|---|---|
| CH (1) | CH176255A (en) |
-
1932
- 1932-07-22 CH CH176255D patent/CH176255A/en unknown
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