DE2627533A1 - Increasing solubility (rate) and resorption of digoxin - by using a solid dispersion with hydroxyalkyl theophylline or theobromine derivs. - Google Patents
Increasing solubility (rate) and resorption of digoxin - by using a solid dispersion with hydroxyalkyl theophylline or theobromine derivs.Info
- Publication number
- DE2627533A1 DE2627533A1 DE19762627533 DE2627533A DE2627533A1 DE 2627533 A1 DE2627533 A1 DE 2627533A1 DE 19762627533 DE19762627533 DE 19762627533 DE 2627533 A DE2627533 A DE 2627533A DE 2627533 A1 DE2627533 A1 DE 2627533A1
- Authority
- DE
- Germany
- Prior art keywords
- digoxin
- theophylline
- theobromine
- dispersion
- dissolving
- 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.)
- Withdrawn
Links
- 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 title claims abstract description 20
- 229960005156 digoxin Drugs 0.000 title claims abstract description 20
- 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 title claims abstract description 20
- 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 title claims abstract description 20
- 239000007962 solid dispersion Substances 0.000 title claims abstract description 11
- YAPQBXQYLJRXSA-UHFFFAOYSA-N theobromine Chemical compound CN1C(=O)NC(=O)C2=C1N=CN2C YAPQBXQYLJRXSA-UHFFFAOYSA-N 0.000 title claims abstract description 10
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N Theophylline Natural products O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 229960004559 theobromine Drugs 0.000 title claims abstract description 5
- 229960000278 theophylline Drugs 0.000 title claims abstract description 4
- -1 hydroxyalkyl theophylline Chemical compound 0.000 title abstract description 4
- 238000000034 method Methods 0.000 claims abstract description 11
- 238000002844 melting Methods 0.000 claims abstract description 7
- 230000008018 melting Effects 0.000 claims abstract description 7
- 238000004090 dissolution Methods 0.000 claims abstract description 6
- 238000004108 freeze drying Methods 0.000 claims abstract description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims abstract description 3
- 239000003960 organic solvent Substances 0.000 claims abstract description 3
- 238000001694 spray drying Methods 0.000 claims abstract description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract 2
- 239000006185 dispersion Substances 0.000 claims description 5
- 238000010521 absorption reaction Methods 0.000 claims description 4
- NWPRCRWQMGIBOT-UHFFFAOYSA-N 7-(2-hydroxyethyl)-1,3-dimethylpurine-2,6-dione Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CCO)C=N2 NWPRCRWQMGIBOT-UHFFFAOYSA-N 0.000 claims description 3
- KYHQZNGJUGFTGR-UHFFFAOYSA-N Proxyphylline Chemical compound CN1C(=O)N(C)C(=O)C2=C1N=CN2CC(O)C KYHQZNGJUGFTGR-UHFFFAOYSA-N 0.000 claims description 3
- 239000012736 aqueous medium Substances 0.000 claims description 3
- KSCFJBIXMNOVSH-UHFFFAOYSA-N dyphylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1N(CC(O)CO)C=N2 KSCFJBIXMNOVSH-UHFFFAOYSA-N 0.000 claims description 2
- 229960005387 etofylline Drugs 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 229960004767 proxyphylline Drugs 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- VQAONJFHIZIRCT-UHFFFAOYSA-N 3-(3-hydroxypropyl)-7-methylpurine-2,6-dione Chemical compound OCCCN1C(NC(C=2N(C=NC1=2)C)=O)=O VQAONJFHIZIRCT-UHFFFAOYSA-N 0.000 claims 1
- JFSTYZPMUQGEEN-UHFFFAOYSA-N 3-(4-hydroxybutyl)-7-methylpurine-2,6-dione Chemical compound OCCCCN1C(NC(C=2N(C=NC1=2)C)=O)=O JFSTYZPMUQGEEN-UHFFFAOYSA-N 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 abstract 1
- 238000001704 evaporation Methods 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 229930182470 glycoside Natural products 0.000 description 4
- 150000002338 glycosides Chemical class 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- GHGVDQNEKGZLPE-UHFFFAOYSA-N 1-(3-hydroxypropyl)-3,7-dimethylpurine-2,6-dione Chemical compound CN1C(=O)N(CCCO)C(=O)C2=C1N=CN2C GHGVDQNEKGZLPE-UHFFFAOYSA-N 0.000 description 1
- MGUBQPRSQWCLCX-UHFFFAOYSA-N 3,7-dimethylpurine-2,6-dione Chemical class CN1C(=O)NC(=O)C2=C1N=CN2C.CN1C(=O)NC(=O)C2=C1N=CN2C MGUBQPRSQWCLCX-UHFFFAOYSA-N 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 229940097217 cardiac glycoside Drugs 0.000 description 1
- 239000002368 cardiac glycoside Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- LPMXVESGRSUGHW-HBYQJFLCSA-N ouabain Chemical compound O[C@@H]1[C@H](O)[C@@H](O)[C@H](C)O[C@H]1O[C@@H]1C[C@@]2(O)CC[C@H]3[C@@]4(O)CC[C@H](C=5COC(=O)C=5)[C@@]4(C)C[C@@H](O)[C@@H]3[C@@]2(CO)[C@H](O)C1 LPMXVESGRSUGHW-HBYQJFLCSA-N 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- MXRGZXBFSKSZPH-UHFFFAOYSA-N protheobromine Chemical compound O=C1N(CC(O)C)C(=O)N(C)C2=C1N(C)C=N2 MXRGZXBFSKSZPH-UHFFFAOYSA-N 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
Classifications
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7028—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages
- A61K31/7034—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin
- A61K31/704—Compounds having saccharide radicals attached to non-saccharide compounds by glycosidic linkages attached to a carbocyclic compound, e.g. phloridzin attached to a condensed carbocyclic ring system, e.g. sennosides, thiocolchicosides, escin, daunorubicin
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
- A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
- A61K47/22—Heterocyclic compounds, e.g. ascorbic acid, tocopherol or pyrrolidones
Abstract
Description
Verfahren zur Erhöhung der Löslichkeit Method of increasing solubility
und Auflösungsgeschwindigkeit von Digoxin Die Erfindung betrifft ein Verfahren zur Erhöhung der Löslichkeit und Auflösungsgeschwindigkeit des schwerlöslichen Herzglykosids Digoxin, mit dem Ziel, eine bessere Resorption aus dem Magen-Darm-Trakt zu erreichen. and rate of dissolution of digoxin. The invention relates to a method of increasing the solubility and rate of dissolution of the poorly soluble Cardiac glycoside digoxin, with the aim of better absorption from the gastrointestinal tract to reach.
Die Resorption von Digoxin aus festen Arzneiformen ist aufgrund der Schwerlöslichkeit des Glykosids im Magen-Uarm.Saft häufig unzulänglich. Die Erfindung will die Resorptionsfähigkeit von Digoxin durch Erhöhung der Löslichkeit und Auflösungsgeschwindigkeit verbessern.The absorption of digoxin from solid dosage forms is due to the The glycoside is poorly soluble in the gastro-intestinal fluid; the juice is often inadequate. The invention aims to increase the absorption capacity of digoxin by increasing its solubility and rate of dissolution to enhance.
Die Erfindung besteht darin, daß-das Digoxin in eine Feste Dispersion mit leicht wasserlöslichen Hydroxyalkylxanthinen überführt wird.The invention consists in that-the digoxin in a solid dispersion is transferred with readily water-soluble hydroxyalkylxanthines.
Diese Festen Dispersionen werden in der Weise hergestellt, daß das Digoxin in flüssigen Schmelzen von hydroxyalkylxanthinen gelöst wird, sodaß das Glykosid nach Erstarren der Schmelzen im Dispersionsmittel molekular gelöst vorliegt.These solid dispersions are prepared in such a way that the Digoxin is dissolved in liquid melts of hydroxyalkylxanthines, so that the Glycoside is present in molecularly dissolved form in the dispersant after the melt has solidified.
Zur herstellung der Festen Dispersionen kann man auch in der Weise vorgehen, daß das Digoxin in konzentrierten wäßrigen Lösungen der Hydroxyalkylxanthine gelöst und anschließend einer Gefriertrocknung oder Sprühtrocknung unterworfen wird.For the preparation of the solid dispersions one can also use the method proceed that the digoxin in concentrated aqueous solutions of hydroxyalkylxanthines dissolved and then subjected to freeze drying or spray drying.
Eine weitere Herstellungsmöglichkeit besteht darin, organische Lösungsmittel für das Digoxin und die hydroxyalkylxanthine zu verwenden, in denen diese seneinsam gelöst werden. Nach erfolgter Lösung wird das Lösungsmittel abgezogen und dadurch die Feste Dispersion ausgefällt.Another manufacturing option is to use organic solvents to use for the digoxin and the hydroxyalkylxanthines, in which these are seneinsam be solved. After the solution has taken place, the solvent is drawn off and thereby the solid dispersion precipitated.
Die auf diese Weise erhaltenen Festen Dispersionen des Digoxin in den Hydroxyalkylxanthinen zeigen beim Einbringen in ein wäßriges Medium eine erhöhte Löslichkeit und Lösungsgeschwindigkeit des Digoxins im Verhältnis zu reinem Digoxin oder zu einer reinen Mischung des Digoxins mit hydroxyalkylxanthinen.The solid dispersions of digoxin in the hydroxyalkylxanthines show an increase when introduced into an aqueous medium Solubility and dissolution rate of digoxin in relation to pure digoxin or a pure mixture of digoxin with hydroxyalkylxanthines.
Spezielle Beispiele von Hydroxyalkylxanthinen, die für die Ausführung des Verfahrens in Frage kommen, sind folgende Verbindungen: 1. Derivate des 1,3-Dimethylxanthin (Theophyllin) 7-(ß-Hydroxyäthyl)-theophyllin 7(Dihydroxypropyl)-theophylli 7-(ß-Hydroxypropyl)-theophyllin 2. Derivate des 3,7-Dimethylxanthin (Theobromin) l-(B-Hydroxyäthyl)-theobromin 1-(Dihydroxypropyl )-theobror.in l-(ß-Hydroxypropyl)-theobromin Die angegebenen hydroxyalkylxanthine können sowohl allein als auch aiteinander gemischt als Träger für die beschriebenen Festen Dispersionen zur Anwendung kommen.Specific examples of hydroxyalkylxanthines which are suitable for carrying out the process are the following compounds: 1. Derivatives of 1,3-dimethylxanthine (theophylline) 7- (ß-hydroxyethyl) -theophylline 7 (dihydroxypropyl) theophylli 7- (ß-hydroxypropyl) -theophylline 2. Derivatives of 3,7-dimethylxanthine (theobromine) l- (B-hydroxyethyl) theobromine 1- (dihydroxypropyl) -theobror.in 1- (β-hydroxypropyl) -theobromine The specified hydroxyalkylxanthines can be used either alone or mixed with one another as carriers for the solid dispersions described.
Die folgenden Beispiele erläutern die Erfindung.The following examples illustrate the invention.
Beispiel 1 lo g Hydroxyäthyltheophyllin (Schmp. 161 - 1640C) werden geschmolzen. In die klare Schmelze werden loo mg Digoxin (Schmp. 240-2500C) eingegeben.Nach klarer Lösung des Glykosids im geschmolzenen Träger wird die Dispersion bis zum Erstarren langsam abgekühlt. Während des gesamten Herstellungsvorgangs sorgt kontinuierliches Rühren für eine homogene Verteilung des Glykosids im Träger.Example 1 lo g of hydroxyethyl theophylline (melting point 161-1640C) are used melted. 100 mg digoxin (melting point 240-2500 ° C.) are added to the clear melt clear solution of the glycoside in the molten carrier, the dispersion is up to Solidify slowly cooled. Throughout the manufacturing process ensures continuous Stir for a homogeneous distribution of the glycoside in the carrier.
Die erstarrte Feste Dispersion , ein kompakter weißer Körper, wird zu feinem Pulver zerkleinert.The solidified solid dispersion, a compact white body, becomes crushed to a fine powder.
Beispiel 2 lo g Dihydroxypropyltheophyllin (Schmp. 160-1630C) und loo mg Digoxin werden wie unter Beispiel 1 beschrieben behandelt.Example 2 lo g of dihydroxypropyltheophylline (melting point 160-1630C) and 100 mg digoxin are treated as described in Example 1.
Beispiel 3 lo g hydroxypropyltheophyllin (Schmp. 133-1360C) und loo mg Digoxin werden wie unter Beispiel 1 beschrieben behandelt.Example 3 lo g of hydroxypropyltheophylline (melting point 133-1360C) and loo mg digoxin are treated as described in Example 1.
Beispiel 4 lo g Hydroxypropyltheobromin (Schmp. 141-144QC) und loo mg Digoxin werden wie unter Beispiel 1 beschrieben behandelt.Example 4 lo g of hydroxypropyl theobromine (melting point 141-144QC) and loo mg digoxin are treated as described in Example 1.
Claims (6)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762627533 DE2627533A1 (en) | 1976-06-19 | 1976-06-19 | Increasing solubility (rate) and resorption of digoxin - by using a solid dispersion with hydroxyalkyl theophylline or theobromine derivs. |
| DE19803000812 DE3000812A1 (en) | 1976-06-19 | 1980-01-11 | Rutin solubility and dissolution rate improvement - by conversion into solid dispersions in hydroxyalkyl-theophylline or -theobromine derivs. e.g. hydroxyethyl-theophylline |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19762627533 DE2627533A1 (en) | 1976-06-19 | 1976-06-19 | Increasing solubility (rate) and resorption of digoxin - by using a solid dispersion with hydroxyalkyl theophylline or theobromine derivs. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2627533A1 true DE2627533A1 (en) | 1977-12-29 |
Family
ID=5980940
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762627533 Withdrawn DE2627533A1 (en) | 1976-06-19 | 1976-06-19 | Increasing solubility (rate) and resorption of digoxin - by using a solid dispersion with hydroxyalkyl theophylline or theobromine derivs. |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2627533A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0864326A2 (en) * | 1997-03-12 | 1998-09-16 | Knoll Ag | Multiphasic preparation comprising an active agent |
| US6787157B1 (en) | 1998-03-10 | 2004-09-07 | Abbott Laboratories | Multiphase active ingredient-containing formulations |
| CN106309392A (en) * | 2016-09-30 | 2017-01-11 | 南京斯泰尔医药科技有限公司 | Methyldigoxin preparation capable of being rapidly absorbed in oral cavity and preparation method of methyldigoxin preparation |
-
1976
- 1976-06-19 DE DE19762627533 patent/DE2627533A1/en not_active Withdrawn
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0864326A2 (en) * | 1997-03-12 | 1998-09-16 | Knoll Ag | Multiphasic preparation comprising an active agent |
| EP0864326A3 (en) * | 1997-03-12 | 2000-11-22 | Knoll Ag | Multiphasic preparation comprising an active agent |
| US6787157B1 (en) | 1998-03-10 | 2004-09-07 | Abbott Laboratories | Multiphase active ingredient-containing formulations |
| CN106309392A (en) * | 2016-09-30 | 2017-01-11 | 南京斯泰尔医药科技有限公司 | Methyldigoxin preparation capable of being rapidly absorbed in oral cavity and preparation method of methyldigoxin preparation |
| CN106309392B (en) * | 2016-09-30 | 2021-10-19 | 南京斯泰尔医药科技有限公司 | Oral fast absorption preparation of methyl digoxin and preparation method thereof |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: KNOLL AG, 6700 LUDWIGSHAFEN, DE |
|
| 8141 | Disposal/no request for examination |