DE2027577C3 - Glycirrhetinic acid esters, their production and pharmaceutical preparations containing them - Google Patents
Glycirrhetinic acid esters, their production and pharmaceutical preparations containing themInfo
- Publication number
- DE2027577C3 DE2027577C3 DE19702027577 DE2027577A DE2027577C3 DE 2027577 C3 DE2027577 C3 DE 2027577C3 DE 19702027577 DE19702027577 DE 19702027577 DE 2027577 A DE2027577 A DE 2027577A DE 2027577 C3 DE2027577 C3 DE 2027577C3
- Authority
- DE
- Germany
- Prior art keywords
- glycirrhetinic
- acid esters
- pharmaceutical preparations
- glycirrhetinic acid
- radical
- 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
- 150000002148 esters Chemical class 0.000 title claims description 10
- 239000002253 acid Substances 0.000 title claims description 9
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- -1 chlorine or bromine Chemical class 0.000 claims description 8
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- 239000007787 solid Substances 0.000 claims description 5
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical group C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 206010030113 Oedema Diseases 0.000 description 4
- 239000003701 inert diluent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 235000010418 carrageenan Nutrition 0.000 description 3
- 229920001525 carrageenan Polymers 0.000 description 3
- 239000008101 lactose Substances 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 125000000490 cinnamyl group Chemical group C(C=CC1=CC=CC=C1)* 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- LVGKNOAMLMIIKO-UHFFFAOYSA-N Elaidinsaeure-aethylester Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC LVGKNOAMLMIIKO-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 208000025865 Ulcer Diseases 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 235000010216 calcium carbonate Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000007891 compressed tablet Substances 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 230000001804 emulsifying effect Effects 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
- 229940093471 ethyl oleate Drugs 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940057995 liquid paraffin Drugs 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 150000002895 organic esters Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
- UORVCLMRJXCDCP-UHFFFAOYSA-N propynoic acid Chemical compound OC(=O)C#C UORVCLMRJXCDCP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
-
- 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
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/215—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids
- A61K31/235—Esters, e.g. nitroglycerine, selenocyanates of carboxylic acids having an aromatic ring attached to a carboxyl group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/95—Esters of quinone carboxylic acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Emergency Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
1515th
JO Methyl-, Äthyl-, Isoprqpyl- und n-Hexy|reste, Allyl- und Vinylreste, Methoxy-, Äthoxy- und Isopropoxyreste, JO methyl, ethyl, isopropyl and n-hexyl radicals, allyl and vinyl radicals, methoxy, ethoxy and isopropoxy radicals,
Die neuen erfindungsgemäßen Verbindungen können hergestellt werden, indem man in an sich bekannter Weise ein 3-Acetylglyzirrhetinsäurechlorid mit einer Verbindung der allgemeinen Formel R-OH, in der R die obengenannte Bedeutung besitzt, in Gegenwart von Pyridin unter wasserfreien Bedingungen bei Rückfluß-· temperatur umsetzt.The new compounds according to the invention can be prepared by using a method known per se Way a 3-acetylglycirrhetinic acid chloride with a Compound of the general formula R-OH, in which R has the abovementioned meaning, in the presence of Reacts pyridine under anhydrous conditions at reflux temperature.
Das folgende Beispiel soll die vorliegende Erfindung erläutern.The following example is intended to illustrate the present invention.
Man vermischt 20 g 3-O-Acetyl-18/)-glyzirrhetinsäurechlorid,
20 ml Propargylalkohol und 100 ml Pyridin und kocht das Gemisch 3 Stunden lang unter Rückfluß
weiter. Man läßt die Reaktionsmischung abkühlen und gießt sie dann in eine Mischung von Eiswasser und
überschüssige Chlorwasserstoffsäure. Die gebildete ölige Masse verfestigt sich rasch beim Steher, und das
feste Material wird abfiltriert, mit Wasser und Methanol gewaschen und getrocknet. Das getrocknete Produkt
wird aus Methanol/Dichlormethan umkristallisierL Man
erhält 3-O-Acetyl-glyzirrhetinsäurepropargylester mit
einem Schmelzpunkt von 227-229°C; [a]v'= 1443° (c = 1% in Chloroform).
Ausbeute: 65% der Theorie.20 g of 3-O-acetyl-18 /) - glycirrhetinic acid chloride, 20 ml of propargyl alcohol and 100 ml of pyridine are mixed and the mixture is refluxed for a further 3 hours. The reaction mixture is allowed to cool and then poured into a mixture of ice water and excess hydrochloric acid. The oily mass formed rapidly solidifies on the stand and the solid material is filtered off, washed with water and methanol and dried. The dried product is recrystallized from methanol / dichloromethane. Propargylic acid 3-O-acetyl-glycirrhetinate is obtained with a melting point of 227-229 ° C .; [a] v '= 1443 ° (c = 1% in chloroform).
Yield: 65% of theory.
Die folgenden Verbindungen wurden auf analoge Weise hergestellt:The following compounds were made in an analogous manner:
J5 Ausbeute Fp. Y5 yield m.p.
I D I D
Eugenyl
CinnamylEugenyl
Cinnamyl
70% 256-257°C + 174"
83% 189-1900C + 154,2°70% 256-257 ° C + 174 "
83% 189-190 0 C + 154.2 °
3-MethyI-pent-l-inyl 40% 254-255°C + 122,8"3-methyl-pent-1-ynyl 40% 254-255 ° C + 122.8 "
Die vorliegende Erfindung betrifft neue pharmazeutisch interessante Glyzirrhetinsäureester, ihre Herstellung sowie antiinflammatorische, pharmazeutische Zubereitungen, die diese neuen Ester enthalten.The present invention relates to new pharmaceutically interesting glycirrhetinic acid esters, their preparation as well as anti-inflammatory pharmaceutical preparations containing these new esters.
Die neuen Glyzirrhetinsäureester der vorliegenden Erfindung sind Verbindungen der allgemeinen Formel:The new glycirrhetinic acid esters of the present invention are compounds of the general formula:
COORCOOR
CH3COCH 3 CO
worin R einen Äthenylrest, der einen unsubstituierten ho oder substituierten Phenylrest trägt, oder einen Alkinylrest mit bis zu 6 C-Atomen oder einen substituierten Phenylrest. bedeutet, wobei die Substituenten Alkyl, Alkenyl, Alkinyl und Alkoxy mit bis zu 6 C-Atomen oder Halogen, wie Chlor oder Brom, hi bedeuten.wherein R is an Äthenylrest, which is an unsubstituted ho or substituted phenyl radical, or an alkynyl radical with up to 6 carbon atoms or one substituted phenyl radical. means, where the substituents are alkyl, alkenyl, alkynyl and alkoxy with up to 6 C atoms or halogen, such as chlorine or bromine, hi mean.
Beispiele für Substituenten, von denen einer oder mehrere in den Phenylresten vorliegen können, sindExamples of substituents, one or more of which can be present in the phenyl radicals, are
Die vorliegende Erfindung betrifft auch pharmazeutische Zubereitungen, weiche die neuen Glyzirrhetinsäureester enthalten. Diese pharmazeutischen Zubereitungen können oral oder parenteral im Gemisch mit einem üblichen festen oder flüssigen pharmazeutischen Träger verabreicht werden.The present invention also relates to pharmaceutical preparations containing the new glycirrhetinic acid esters contain. These pharmaceutical preparations can be used orally or parenterally in admixture with a conventional solid or liquid pharmaceutical carriers are administered.
Zu festen Zubereitungen für die orale Verabreichung gehören gepreßte Tabletten, Pillen, dispergierbare Pulver und Granulate. In derartigen festen Zubereitungen wird einer der neuen Ester mit wenigstens einem inerten Verdünnungsmittel, wie Calciumcarbonat, Stärke, Alginsäure oder Lactose vermischt. i>ie Zubereitungen können auch — wie es üblich ist — andere zusätzliche Substanzen als die inerten Verdünnungsmittel, z. B. Gleitmittel, wie Magnesiumstearat, enthalten.Solid preparations for oral administration include compressed tablets, pills, dispersible ones Powder and granules. In such solid preparations, one of the new esters is with at least one inert diluents such as calcium carbonate, starch, alginic acid or lactose. i> ie preparations can also - as is usual - other additional substances than the inert diluents, z. B. contain lubricants such as magnesium stearate.
Flüssige Zubereitungen zur oralen Verabreichung sind pharmazeutisch verträgliche Emulsionen, Lösungen, Suspensionen, Sirups und Elixiere, die übliche inerte Verdünnungsmittel enthalten, wie Wasser und flüssiges Paraffin. Neben inerten Verdünnungsmitteln können derartige Zusammensetzungen auch Adjuvantien, wie Benetzungs- und Suspendiermittel, sowie Süß- und Aromastoffe enthalten.Liquid preparations for oral administration are pharmaceutically acceptable emulsions, solutions, Suspensions, syrups and elixirs containing common inert diluents such as water and liquid Paraffin. In addition to inert diluents, compositions of this type can also contain adjuvants, such as Contains wetting and suspending agents, as well as sweeteners and flavorings.
Die erfindungsgemäßen Zubereitungen zur oralen Verabreichung schließen Kapseln aus absorbierbarem Material, wie Gelatine, ein, die eines der neuen Derivate mit oder ohne Zusat;: von Verdünnungsmittel oder Trägerstoff enthalten.The preparations according to the invention for oral administration include capsules made of absorbable Material, such as gelatin, one of the new derivatives with or without additive ;: of diluent or Contain carrier.
Zu erfindungsgemäßen Zubereitungen für die parenteral Verabreichung gehören sterile, wäßrige oder nichtwäßrige Lösungen, Suspensionen oder Emulsionen, Zu Beispielen für nichtwäßrige Lösungsmittel oder suspendierende Medien gehören Propylenglykol, Polyäthylenglykol, pflanzliche Öle, wie Olivenöl, und injizierbare organische Ester, wie Äthyloleat Diese Zubereitungen können auch Adjuvantien enthalten, wie Benetzungs-, Emulgier- und Dispergiermittel. Sie können sterilisiert werden, beispielsweise durch Filtration durch Bakterien zurückhaltende Filter, oder dadurch, daß man den Zubereitungen sterilisierende Mittel einverleibt oder durch Bestrahlung oder durch Erhitzen. Sie können auch in Form von sterilen, festen Zubereitungen hergestellt werden, die in sterilem Wasser oder einem anderen sterilen, injizierbaren Medium unmittelbar vor der Verwendung gelöst werden können.For preparations according to the invention for parenteral Administration includes sterile, aqueous or non-aqueous solutions, suspensions or emulsions, Examples of non-aqueous solvents or suspending media include propylene glycol, polyethylene glycol, vegetable oils such as olive oil; and injectable organic esters such as ethyl oleate These Preparations can also contain adjuvants, such as wetting, emulsifying and dispersing agents. she can be sterilized, for example by filtration through bacteria-retaining filters, or by incorporating sterilizing agents into the preparations or by irradiation or by Heat. They can also be made in the form of sterile, solid preparations that are sterile Water or other sterile injectable medium dissolved immediately prior to use can be.
Der Prozentsatz an aktivem Material in den Zubereitungen der vorliegenden Erfindung kann variiert werden, so daß eine geeignete Dosierung für den gewünschten therapeutischen Zweck erhalten wird. Im allgemeinen sollten die Präparate der vorliegenden Erfindung dem Menschen oral oder parenteral mit 10 bis 1000 mg, vorzugsweise 50 bis 500 mg, aktiver Substanz pro Tag verabreicht werden.The percentage of active material in the formulations of the present invention can vary so that a suitable dosage for the desired therapeutic purpose is obtained. in the In general, the preparations of the present invention should be administered to humans orally or parenterally at 10 up to 1000 mg, preferably 50 to 500 mg, of active substance are administered per day.
Die folgenden Beispiele veranschaulichen erfindungsgemäße pharmazeutische Zubereitungen:The following examples illustrate pharmaceutical preparations according to the invention:
Es werden 250 mg Tabletten hergestellt, die folgendes enthalten:250 mg tablets are made that contain:
3-O-Aceiyl-glyzirrhetinsaure-3-O-acceiyl-glycirrhetinic acid
eugenylester 50 mgeugenyl ester 50 mg
Stärke 100 mgStrength 100 mg
Lactose 95 mgLactose 95 mg
Magnesiumstearat 5 mgMagnesium stearate 5 mg
Es werden 400-mg-Tabletten hergestellt, die folgendes enthalten:400 mg tablets are made that have the following contain:
20 Die Zubereitungen gemäß den Beispielen 2 und 3 sind für die orale Verabreichung beim Menschen zur Behandlung von ulcerativen Zuständen der Magenschleimhaut bestimmt 20 The formulations according to Examples 2 and 3 are intended for oral administration in humans for the treatment of ulcerative conditions of the gastric mucosa
Die überlegenen Eigenschaften der erfindungsgemäßen Verbindungen gehen aus folgendem Versuchsbericht hervor:The superior properties of the compounds according to the invention are evident from the following test report emerged:
Mit vier Verbindungen gemäß der vorliegenden Erfindung und einer bekannten Verbindung (R = Oleyl) jo wurden unter Anwendung des Carrageeninödemtests Vergleichsversuche durchgeführt.With four compounds according to the present invention and one known compound (R = oleyl) jo comparative tests were carried out using the carrageenin edema test.
Die erhaltenen Ergebnisse sind in der folgenden Tabelle zusammengesteilt:The results obtained are summarized in the following table:
Wirkungen der Verbindungen bei dem CarrageeninödemtestEffects of the compounds on the carrageenin edema test
PropargylPropargyl
EugenylEugenyl
CinnamylCinnamyl
3-MethyIpent-l-yn-l-yl
Oleyl*)3-methylpent-1-yn-1-yl
Oleyl *)
*) Verglcichsverhindung gemäß dem Stand der Technik.*) Comparison according to the state of the art.
4Std.Wh; .i.ng /%
4h
mg/kgdose
mg / kg
i.p.ip
ip
20,719.6
20.7
> 2400 i.p.> 2400 ip
> 2400 ip
100200
100
oralip
orally
1727.1
17th
10200
10
s.c.
s.c.orally
sc
sc
13
2628
13th
26th
10
100100
10
100
oralip
orally
623.3
6th
10200
10
s.c.orally
sc
1312.8
13th
100100
100
Aus der obigen Tabelle ist ersichtlich, daß die Toxizität (LD50) der erfindungsgemäßen Verbindungen erheblich geringer als diejenige der bekannten Verbindung ist. Weilerhin sind auch die Ergebnisse beim Carrageeninödemtest bei den erfindungsgemäßen Verbj bindungen erheblich besser als bei der bekannten Verbindung.From the table above it can be seen that the toxicity (LD50) of the compounds according to the invention is considerably less than that of the known compound. After all, the results are there too The carrageenin edema test of the compounds according to the invention is considerably better than that of the known one Link.
Claims (1)
I. Glyzirrhetinsäureester der allgemeinen FormelClaims;
I. Glycirrhetinic acid esters of the general formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE20221518U DE20221518U1 (en) | 1970-06-04 | 2002-12-10 | Modular domestic communications system has at least some modular door and/or dwelling stations with main module similar to electrical installation device and functional module(s) |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB5321369A GB1255672A (en) | 1969-06-06 | 1969-06-06 | Glycyrrhetinic acid esters |
| GB2878069 | 1969-06-06 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2027577A1 DE2027577A1 (en) | 1970-12-10 |
| DE2027577B2 DE2027577B2 (en) | 1977-12-22 |
| DE2027577C3 true DE2027577C3 (en) | 1978-08-24 |
Family
ID=26259569
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19702027577 Expired DE2027577C3 (en) | 1969-06-06 | 1970-06-04 | Glycirrhetinic acid esters, their production and pharmaceutical preparations containing them |
Country Status (2)
| Country | Link |
|---|---|
| JP (1) | JPS54909B1 (en) |
| DE (1) | DE2027577C3 (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU553789B2 (en) * | 1982-06-30 | 1986-07-24 | Biorex Laboratories Ltd. | Glycyrrhetinic acid derivatives in cream compositions |
-
1970
- 1970-06-04 DE DE19702027577 patent/DE2027577C3/en not_active Expired
- 1970-06-04 JP JP4768370A patent/JPS54909B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS54909B1 (en) | 1979-01-18 |
| DE2027577B2 (en) | 1977-12-22 |
| DE2027577A1 (en) | 1970-12-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |