DE19722831A1 - New vehicle system comprising stable, ternary mixed micelles - Google Patents
New vehicle system comprising stable, ternary mixed micellesInfo
- Publication number
- DE19722831A1 DE19722831A1 DE1997122831 DE19722831A DE19722831A1 DE 19722831 A1 DE19722831 A1 DE 19722831A1 DE 1997122831 DE1997122831 DE 1997122831 DE 19722831 A DE19722831 A DE 19722831A DE 19722831 A1 DE19722831 A1 DE 19722831A1
- Authority
- DE
- Germany
- Prior art keywords
- stable
- mixed micelles
- vehicle systems
- vehicle system
- ternary mixed
- 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- Withdrawn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
- 239000000693 micelle Substances 0.000 title claims abstract description 12
- 239000003833 bile salt Substances 0.000 claims abstract description 15
- 239000003814 drug Substances 0.000 claims abstract description 12
- 229940093761 bile salts Drugs 0.000 claims abstract description 7
- 150000003904 phospholipids Chemical class 0.000 claims abstract description 7
- 150000004668 long chain fatty acids Chemical class 0.000 claims abstract description 3
- 229940079593 drug Drugs 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 5
- 239000000787 lecithin Substances 0.000 claims description 3
- 235000010445 lecithin Nutrition 0.000 claims description 3
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 2
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 claims description 2
- 239000005642 Oleic acid Substances 0.000 claims description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 2
- DTOSIQBPPRVQHS-PDBXOOCHSA-N alpha-linolenic acid Chemical compound CC\C=C/C\C=C/C\C=C/CCCCCCCC(O)=O DTOSIQBPPRVQHS-PDBXOOCHSA-N 0.000 claims description 2
- 235000020661 alpha-linolenic acid Nutrition 0.000 claims description 2
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 2
- 235000020778 linoleic acid Nutrition 0.000 claims description 2
- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 claims description 2
- 229960004488 linolenic acid Drugs 0.000 claims description 2
- KQQKGWQCNNTQJW-UHFFFAOYSA-N linolenic acid Natural products CC=CCCC=CCC=CCCCCCCCC(O)=O KQQKGWQCNNTQJW-UHFFFAOYSA-N 0.000 claims description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 2
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 2
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 2
- AQHHHDLHHXJYJD-UHFFFAOYSA-N propranolol Chemical compound C1=CC=C2C(OCC(O)CNC(C)C)=CC=CC2=C1 AQHHHDLHHXJYJD-UHFFFAOYSA-N 0.000 description 8
- 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 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000013543 active substance Substances 0.000 description 5
- 229960003712 propranolol Drugs 0.000 description 4
- 235000001258 Cinchona calisaya Nutrition 0.000 description 3
- 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 3
- 150000002632 lipids Chemical class 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 229960000948 quinine Drugs 0.000 description 3
- KILNVBDSWZSGLL-KXQOOQHDSA-N 1,2-dihexadecanoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCCCCCCCCCCCCCC KILNVBDSWZSGLL-KXQOOQHDSA-N 0.000 description 2
- IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 2
- WBWWGRHZICKQGZ-UHFFFAOYSA-N Taurocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCCS(O)(=O)=O)C)C1(C)C(O)C2 WBWWGRHZICKQGZ-UHFFFAOYSA-N 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 229940067606 lecithin Drugs 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- WBWWGRHZICKQGZ-GIHLXUJPSA-N taurocholic acid Chemical compound C([C@@H]1C[C@H]2O)[C@@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@@H]([C@@H](CCC(=O)NCCS(O)(=O)=O)C)[C@@]2(C)[C@H](O)C1 WBWWGRHZICKQGZ-GIHLXUJPSA-N 0.000 description 2
- METKIMKYRPQLGS-GFCCVEGCSA-N (R)-atenolol Chemical compound CC(C)NC[C@@H](O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-GFCCVEGCSA-N 0.000 description 1
- -1 B. lecithin Chemical class 0.000 description 1
- 108010007979 Glycocholic Acid Proteins 0.000 description 1
- RFDAIACWWDREDC-UHFFFAOYSA-N Na salt-Glycocholic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(=O)NCC(O)=O)C)C1(C)C(O)C2 RFDAIACWWDREDC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 description 1
- 229960002274 atenolol Drugs 0.000 description 1
- 210000005178 buccal mucosa Anatomy 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 1
- 229960005091 chloramphenicol Drugs 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- DCOPUUMXTXDBNB-UHFFFAOYSA-N diclofenac Chemical compound OC(=O)CC1=CC=CC=C1NC1=C(Cl)C=CC=C1Cl DCOPUUMXTXDBNB-UHFFFAOYSA-N 0.000 description 1
- 229960001259 diclofenac Drugs 0.000 description 1
- 239000005350 fused silica glass Substances 0.000 description 1
- 210000001035 gastrointestinal tract Anatomy 0.000 description 1
- RFDAIACWWDREDC-FRVQLJSFSA-N glycocholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 RFDAIACWWDREDC-FRVQLJSFSA-N 0.000 description 1
- 229940099347 glycocholic acid Drugs 0.000 description 1
- WVULKSPCQVQLCU-BUXLTGKBSA-N glycodeoxycholic acid Chemical compound C([C@H]1CC2)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(=O)NCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 WVULKSPCQVQLCU-BUXLTGKBSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000008363 phosphate buffer Substances 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 230000007928 solubilization Effects 0.000 description 1
- 238000005063 solubilization Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0019—Injectable compositions; Intramuscular, intravenous, arterial, subcutaneous administration; Compositions to be administered through the skin in an invasive manner
-
- 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
- A61K47/28—Steroids, e.g. cholesterol, bile acids or glycyrrhetinic acid
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/107—Emulsions ; Emulsion preconcentrates; Micelles
- A61K9/1075—Microemulsions or submicron emulsions; Preconcentrates or solids thereof; Micelles, e.g. made of phospholipids or block copolymers
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Dermatology (AREA)
- Biophysics (AREA)
- Molecular Biology (AREA)
- Dispersion Chemistry (AREA)
- Medicinal Preparation (AREA)
Abstract
Description
Bisher werden verschiedene binäre mischmizellare Systeme als Vehikel für Arzneistoffe eingesetzt (siehe Tabelle 1). Diese Vehikelsysteme bestehen aus Trihydroxygallensäuren/-salzen, z. B. Glycocholsäure oder Taurocholsäure, und Phospholipiden, z. B. Lecithin, oder gesättigten Fettsäuren.So far, various binary mixed micellar systems have been used as vehicles for drugs used (see Table 1). These vehicle systems consist of Trihydroxygallen acids / salts, e.g. B. glycocholic acid or taurocholic acid, and Phospholipids, e.g. B. lecithin, or saturated fatty acids.
Diese Systeme weisen jedoch folgende Nachteile auf, wie z. B.:
However, these systems have the following disadvantages, such as. B .:
- - geringe Aufnahmekapazität von Arzneistoffen und- low absorption capacity of drugs and
- - geringe Stabilität der mischmizellaren Systeme.- low stability of the mixed micellar systems.
Die bisher beschriebenen Systeme genügen hinsichtlich der Aufnahmekapazität von Arzneistoffen und der Stabilität der Mischmizellen nicht den Anforderungen an Phar mazeutika bzw. Kosmetika.The systems described so far are sufficient in terms of the absorption capacity of Drugs and the stability of the mixed micelles do not meet the requirements for Phar pharmaceuticals or cosmetics.
Der im Patentanspruch (1) angegebenen Erfindung liegt das Problem zugrunde, durch
neue Vehikelsysteme für Arzneistoffe (AS) die Steuerung bzw. Verbesserung folgender
Prozesse dieser Arzneistoffe zu erzielen:
The invention specified in patent claim (1) is based on the problem of using new vehicle systems for medicinal substances (AS) to control or improve the following processes of these medicinal substances:
- - Penetration in und durch die Haut,- penetration into and through the skin,
- - Resorption aus dem Gastrointestinaltrakt,Absorption from the gastrointestinal tract,
- - Solubilisation und Dauer der Wirksamkeit nach parenteraler Applikation und- Solubilization and duration of effectiveness after parenteral administration and
- - Applikation über Schleimhäute, z. B. über die Bukkal- oder Nasenschleimhaut.- Application over mucous membranes, e.g. B. on the buccal or nasal mucosa.
Diese Probleme werden durch die im Patentanspruch (1) aufgeführten Vehikelsysteme gelöst, die aus stabilen, ternären Mischmizellen auf der Basis von Dihydroxygallensalzen, Phospholipiden und ungesättigten, langkettigen Fettsäuren bestehen. Als Mischungs verhältnisse kommen Gallensalz/Phospholipid/Fettsäure = 20/5-10/2-20 mM in Frage. Die Stabilität der Mischmizellen sowie eine hohe Affinität der Wirkstoffe zu den Mischmizellen wird durch die Anwesenheit von Dihydroxygallensalzen erreicht (siehe Tabelle 2-4). Es hat sich gezeigt, daß für diesen Verwendungszweck, d. h. zur Her stellung stabiler Mischmizellen und zum Erreichen einer hohen Aufnahmekapazität für Arzneistoffe, Dihydroxygallensalze besser geeignet sind als die bisher verwendeten Trihydroxygallensalze (siehe Tabelle 2). Es hat sich weiterhin gezeigt, daß die ternären, mischmizellaren Systeme gemäß dieser Erfindung gegenüber Arzneistoffen eine weitaus größere Aufnahmekapazität aufweisen als die binären, mischmizellaren Systeme, die bisher beschrieben wurden (siehe Tabelle 4).These problems are caused by the vehicle systems listed in claim (1) solved that from stable, ternary mixed micelles based on dihydroxygallen salts, Phospholipids and unsaturated, long-chain fatty acids exist. As a mix conditions bile salt / phospholipid / fatty acid = 20 / 5-10 / 2-20 mM. The stability of the mixed micelles as well as a high affinity of the active substances to the Mixed micelles are achieved by the presence of dihydroxy bile salts (see Table 2-4). It has been shown that for this purpose, i.e. H. to the fro position of stable mixing micelles and to achieve a high absorption capacity for Drugs, dihydroxy bile salts are more suitable than those previously used Trihydroxy bile salts (see Table 2). It has also been shown that the ternary, mixed micellar systems according to this invention compared to drugs have greater absorption capacity than the binary, mixed-micellar systems that have been described so far (see Table 4).
Als Dihydroxygallensalze eignen sich beispielsweise Desoxycholate Chenodesoxycholate als ungesättigte Fettsäuren, z. B. Olsäure, Linolsäure oder Linolensäure und als Phospholipide z. B. Phosphatylcholine oder Lecithin.Suitable dihydroxy bile salts are, for example, deoxycholates chenodeoxycholates as unsaturated fatty acids, e.g. As oleic acid, linoleic acid or linolenic acid and as Phospholipids e.g. B. phosphatylcholines or lecithin.
Ausführungsbeispiele der Erfindung sind in der Tabelle 2 bis 4 angegeben.Exemplary embodiments of the invention are given in Tables 2 to 4.
In Tabelle 1: Bisher als Vehikel für Arzneistoffe verwendete binäre Gallensalz-Lipid
gemsiche (Misehzellen)
In Tabelle 2: Abhängigkeit des Kapazitätsfaktors für Propranolol und Chinin von der
Art des Gallensalzes (NaGDC-Na-Glycodesoxycholat, NaTC-Na-Tauro
cholat)
In Tabelle 3: Abhängigkeit des Kapazitätsfaktors für Propranolol und Atenolol von der
Art des Gallensalzes und der Fettsäure (NaGDC-Na-Glycodesoxycholat,
NaTC-Na-Taurocholat)
In Tabelle 4: Abhängigkeit des Kapazitätsfaktor für Propranolol, Chinin und Atenol -
eine Gegenüberstellung von binären und ternären mizellaren Phasen.
In Table 1: Binary bile salt lipid mixture used so far as a vehicle for pharmaceuticals (mis cells)
In table 2: dependence of the capacity factor for propranolol and quinine on the type of bile salt (NaGDC-Na-glycodesoxycholate, NaTC-Na-taurocholate)
In Table 3: Dependence of the capacity factor for propranolol and atenolol on the type of bile salt and the fatty acid (NaGDC-Na-glycodesoxycholate, NaTC-Na-taurocholate)
In table 4: Dependence of the capacity factor for propranolol, quinine and atenol - a comparison of binary and ternary micellar phases.
Bisher als Vehikel für Arzneistoffe verwendete binäre Gallensalz- Lipidgemische (Mischmizellen)Binary bile salt previously used as a vehicle for drugs Lipid mixtures (mixed micelles)
Bisher als Vehikel für Arzneistoffe verwendete binäre Gallensalz- Lipidgemische (Mischmizellen)Binary bile salt previously used as a vehicle for drugs Lipid mixtures (mixed micelles)
Abhängigkeit des Kapazitätsfaktors kmmz (gemischte Mizelle - mmz, simple Mizelle - mz) für Propranolol.
Chinin, Chloramphenicol und Diclofenac von der Konzentration an Dipalmitoylphosphatidylcholin (DPPC) bei
konstanter Gallensalzkonzentration - eine Gegenüberstellung von NaGDC und NaTC (GS - Gallensalz, NaGDC - Na-
Salz der Glycodesoxycholsäure, NaTC - Na-Salz der Taurocholsäure), kmz = nmz/naq (nmz - Stoffmenge des Wirkstoffes
in der mizellaren Phase, naq-Stoffmenge des Wirkstoffes in der wäßrigen Phase) kmmz = nmmz/naq (nmmz-Stoffmenge
des Wirkstoffes in der gemischten mizellaren Phase, naq-Stoffmenge des Wirkstoffes in der wäßrigen Phase)
Dependence of the capacity factor k mmz (mixed micelle - mmz, simple micelle - mz) for propranolol. Quinine, chloramphenicol and diclofenac from the concentration of dipalmitoylphosphatidylcholine (DPPC) at constant bile salt concentration - a comparison of NaGDC and NaTC (GS - bile salt, NaGDC - Na salt of glycodesoxycholic acid, NaTC - Na salt of taurocholic acid), k mz = n mz / n aq (n mz - amount of active substance in the micellar phase, n aq - amount of active substance in the aqueous phase) k mmz = n mmz / n aq (n mmz - amount of active substance in the mixed micellar phase, n aq - Amount of active substance in the aqueous phase)
CE: Hewlett Packard (Waldbronn, Germany) HP3D CE: Hewlett Packard (Waldbronn, Germany) HP 3D
CE System
Kapillare: 600 (515) × 0.05 mm, fused silica
Parameter: 30 kV (positiv), + 50 mbar Druck, 220 nm, 200 [mbar s] Druckinjektion
Puffer: 20 mM Phosphatpuffer, pH = 7.4CE system
Capillary: 600 (515) × 0.05 mm, fused silica
Parameters: 30 kV (positive), + 50 mbar pressure, 220 nm, 200 [mbar s] pressure injection
Buffer: 20 mM phosphate buffer, pH = 7.4
Claims (5)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1997122831 DE19722831A1 (en) | 1997-05-30 | 1997-05-30 | New vehicle system comprising stable, ternary mixed micelles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1997122831 DE19722831A1 (en) | 1997-05-30 | 1997-05-30 | New vehicle system comprising stable, ternary mixed micelles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE19722831A1 true DE19722831A1 (en) | 1998-12-03 |
Family
ID=7831027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1997122831 Withdrawn DE19722831A1 (en) | 1997-05-30 | 1997-05-30 | New vehicle system comprising stable, ternary mixed micelles |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE19722831A1 (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2807248A1 (en) * | 1977-02-28 | 1978-08-31 | Yamanouchi Pharma Co Ltd | PREPARATIONS FOR RECTAL USE |
| DE19522693A1 (en) * | 1995-06-22 | 1997-01-02 | Dianorm G Maierhofer Gmbh | Composition for the production of finely dispersed systems and process for their production |
-
1997
- 1997-05-30 DE DE1997122831 patent/DE19722831A1/en not_active Withdrawn
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2807248A1 (en) * | 1977-02-28 | 1978-08-31 | Yamanouchi Pharma Co Ltd | PREPARATIONS FOR RECTAL USE |
| DE19522693A1 (en) * | 1995-06-22 | 1997-01-02 | Dianorm G Maierhofer Gmbh | Composition for the production of finely dispersed systems and process for their production |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OP8 | Request for examination as to paragraph 44 patent law | ||
| 8139 | Disposal/non-payment of the annual fee |