Derivative of glycyrrhetic acid and method of production thereof

 

(57) Abstract:

Usage: as an antioxidant and anti-inflammatory agents. The inventive product is derived glycyrrhetinate acid f-ly I, where R is H or unsubstituted or substituted alkyl WITH1-C18or its pharmacologically applicable Sol. The product is obtained by the action guidtostring agent on glycerietum acid or its alkilany ether, followed by interaction of the obtained product with ascorbic acid having a protected 5 - and 6-hydroxy-group, which then removes the protection of the hydrolysis. Connection structure of f-crystals I:

< / BR>
2 S. and 6 C. p. F.-ly, 3 ill., table 2.

The invention relates to new and useful derivative of glycyrrhetic acid, processes for their preparation and the use of these derivatives. More specifically, the invention relates to 3-(1-ascorbyl-2-phosphoryl)-glycyrrhetic acid, it is difficult ester derivative, or a pharmacologically applicable salts of such acids, and method of production thereof and to the antioxidant, anti-inflammatory and/or anti-allergic compositions comprising such compounds.

To date ascorbic acid was used as the Jena and inhibits the production of melanin in the body. Recently it was reported that this compound also has anti-cancer activity. On the other hand, it is known that glaciecola acid has anti-inflammatory activity. However, none of these compounds does not have a satisfactory efficiency.

In this regard, the authors of the present invention have made efforts in the search for new, more active compounds and as a result of this work found that the above purpose meets a new connection, corresponding to the fragments of ascorbic acid and glycyrrhetic acid linked via a phosphoric acid residue. Based on this fact it was conceived and developed the present invention.

In connection with the above, the present invention is to obtain compounds of the following formula

< / BR>
CVGin which a represents a hydrogen atom or unsubstituted or substituted alkyl group containing 1-18 carbon atoms, or its pharmaceutically applicable salt, the development of the method of obtaining the compounds or salts thereof, as well as in obtaining antioxidant, anti-inflammatory and/or anti-allergic composition comprising pointed to by the function group, which preferably contains 1 to 18 carbon atoms. Carbon chain such alkyl groups may be linear, branched or cyclic and may even have a ring structure. In addition, such an alkyl group may be optionally substituted by other groups. Such an alkyl group may also be a lower alkyl group as a methyl, ethyl, n-propyl, ISO-propyl, cyclopentyl, n-butyl, tert.-butyl, sec. -butyl, n-pentyl, 1-ethylpropyl, out-of pentyl, n-hexyl, etc., higher alkyl groups as n-decyl, n-heptadecyl, n-octadecyl, etc., including their isomers, and benzyl.

Pharmacologically applicable Sol of the present invention may constitute, among other such alkali metal salts, as sodium salt, potassium salt, etc., such salts of alkaline-earth metals as calcium salt, magnesium salt, etc., But can be synthesized and successfully used any other salt if they are pharmacologically applicable.

The compound of the present invention can be synthesized, for example, as follows. For example, (1) carry out the reaction between glycyrrhetic acid or its alkilany ether with halophosphines agent is the victim groups, and (3) finally, the protective group is removed by hydrolysis. According to this method of obtaining compounds of the present invention, glaciecola acid or its alkilany ether reacts with halophosphines agents in the first place. Typically, this reaction is preferably carried out in the presence of an acid acceptor.

Halofantrine agent can be any compound, with which the remainder halophosphines acid may be introduced into the hydroxyl group of glitsiretovuyu acid or its Olkiluoto ether, and preferably, the agent is phosphoryl chloride or phosphoryl bromide. Although as acid acceptor in this reaction may be used any substance acceptor acid, which is commonly used in reactions of this type, it is preferable to use such an organic amine as pyridine or triethylamine.

Usually, the reaction of phosphorylation in the method of the present invention proceeds smoothly in an environment suitable solvent. The solvent can be any solvent not interfering during the reaction and can generally be used aromatic hydrocarbons such as benzene, toluene, etc. and halogenated hydrocarbons such as chloride, methylundecyl maximally smooth its flow, typically this reaction is carried out at 0 to 50oC. In the specified temperature range the reaction is completed within 1 to 10 hours

Halofantrine this method glycyrrhetic acid or its alkilany ether then reacts with ascorbic acid, the hydroxyl group of which the provisions of articles 5 and 6 pre-reserved. As protective groups for the 5 - and 6-positions of ascorbic acid can be any hydroxy-protective group which can be easily removed after the reaction. So, for this purpose you can use such acyl groups as acetyl, however, the preferred groups are isopropylidene, benzylidene and similar groups.

The reaction specified golfostermann glitsiretovuyu acid or its Olkiluoto ether with the specified ascorbic acid, previously protected in positions 5 or 6, preferably in the environment of a non-polar solvent. Although the preferred examples of such ethers can serve as dioxane and tetrahydrofuran, as nonpolar solvents can be used other substances that do not have undesirable influence on the course of the reaction. Typically, this reaction proceeds smoothly in the presence of an acid acceptor.

This reaction can be successfully carried out at 0 to 50oC and in this case it is completed within 1 to 10 hours

Further, the removal of the hydroxy-protective groups for the 5 - and 6-positions of ascorbic acid and the halogen atom of the fragment residue halophosphines acid obtain the target compound of the present invention. Such removal of the protective groups is preferably carried out by hydrolysis. This hydrolysis reaction is preferably carried out in the presence of acid. As mentioned acids can be used such inorganic acids as hydrochloric acid, sulfuric acid, phosphoric acid, etc., such organic acids as acetic acid, citric acid, etc., the hydrolysis Reaction is preferably conducted in an environment appropriate aqueous solvent. So, with success, you can use a mixture of water and miscible with water and organic solvent. The preferred mixing with the water solvent can be methanol, ethanol, dioxane, tetrahydrofuran, etc.

Conditions of the hydrolysis should be chosen in such a way to make a successful removal of protective groups. Usually, this hydrolysis reaction proceeds smoothly at 0, 50oC and in many cases it Zawiercie applicable Sol, which can be selected, such as using appropriate methods known per se. For example, the compound obtained as described above can be turned into such salt, for example, by the reaction with the compound, donor ions of alkali or alkaline earth metal in an environment suitable solvent. The transformation in such salt can be performed after separation of the compounds of the invention from the reaction mixture or without pre-selection. Connection-donor metal ions can represent, for example, the corresponding hydroxide, carbonate or acid carbonate and any of these substances may be used in the reaction.

The compound of the present invention, which can be obtained by the above method, is a new substance that is not described in the literature and has antioxidant, anti-inflammatory and anti-allergic activities, as well as the ability to stabilize compounds that absorb ultraviolet light and can break even for cosmetic use, so this connection is very useful for these purposes.

In connection with the above multi-action setpolyfillmode or antiallergic agent, but in cosmetics.

Typical diseases that can be treated with anti-oxidation agent of the present invention, are cataracts and various ischemic organic disease.

As an anti-inflammatory agent, the compounds of the present invention can be used to treat a large number of inflammatory diseases, such as hemorrhoidal disease, rheumatoid arthritis, rheumatic deformation, spondylidinae strains, arthritic strain, lumbago, acute otitis media, cystitis, prostatitis, toothache, uveitis, sinusit, etc. In the case of diseases such proposed connection may be used for therapeutic purposes.

As antiallergic agent, the compound of the present invention may be prescribed in these various diseases, allergic-type, such as bronchial asthma, pollinosis, allergic renity, diet allergic gastritis, allergic diarrhea, ulcerative cullity, stomatitis, periarthritis, obliterating endarteritis, endocarditis, urticaria, eczema, contact dermatitis, flecktones, sympathetic ophthalmic, allergic conjunctivitis, allergic carat the change in therapeutic purposes.

As a cosmetic ingredient compound of the present invention can be administered in such formulations as creams, lotions, toilet water, etc., in order to absorb ultraviolet light conditioning of the skin or the stabilization of other components of space vehicles.

Antioxidant, anti-inflammatory and/or anti-allergic composition of the present invention may contain one or more varieties, in appropriate combination, the compounds of the present invention in accordance with the intended use.

Antioxidant, anti-inflammatory and/or anti-allergic composition of the present invention can be used orally or by another method for the prevention or treatment of the above diseases. As for the used dosage forms, such various solid preparations such as tablets, granules, powders, capsules, ointments, suppositories, etc., and such liquid preparations, as eye drops, injections, syrups, etc. can be produced by methods known per se. Upon receipt of such drugs, if necessary, can be used various eccipienti, which are usually used in a pharmaceutical is very, surface-active agents, solubilization protecting agents, emulsifiers, isotonic agents, stabilizers, agents regulating pH etc. When introducing the compound of the invention in space products, together with them can also be applied ingredients typically used in the space industry.

Medical dosage of the compounds of the invention depends on the nature of the connection, the patient's age and weight of his body, used dosage forms, the type and condition of the disease and other factors. In the case of drugs for injection, the daily dose for an adult patient may be 1 to 100 mg. In the case of oral administration can several times a day to apply the dosage of 10 to 1000 mg. In the case of eye drops several times a day, several drops apply the solution with a concentration of 0.1 to 5 wt./about.

The concentration of the compounds of the invention in a cosmetic product may vary depending on the specific type of connection, type of space product name entered the compound and other conditions. However, as a rule, such a connection is used in the concentration range of 0.001 to 5 wt./weight. preferably in the range of 0.01 to 2 wt./weight.

Without breaking the whole the ants, anti-inflammatory and/or anti-allergic agents, and/or other medical active ingredients.

The following examples and test examples are presented for a more detailed description of the invention and they in no way limit the scope of the invention.

Example 1

3-(1-ascorbyl-2-phosphoryl)-glycyrrhetic acid

To a mixture of 4.7 g of glitsiretovuyu acid and 8 ml of pyridine was added 30 ml of dry chloroform and stirring of the solution in terms of cooling with ice, bury 3.2 g of chloride phosphoryla in 30 ml of dry benzene. The resulting mixture was stirred under cooling with ice for 30 min and then for 1.5 h at room temperature. The resulting reaction mixture was concentrated under reduced pressure and the residue was dissolved in 20 ml of benzene. The obtained benzene solution was to bury a mixture of 4 g isopropylidenediphenol acid and 2.5 ml of dry pyridine in 30 ml of dry tetrahydrofuran and the resulting mixture was stirred under ice cooling for 30 min and for 2 h at room temperature. Then the reaction mixture was concentrated under reduced pressure. The remaining oil was added 50 ml of ethanol and 20 ml 0,511 hydrochloric acid and the mixture is Aravali with ethyl acetate and the extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Then the solvent was removed under reduced pressure. To the residue was added n-hexane, and the mixture was stood and the resulting crystals were collected by filtration. By recrystallization from a mixture of n-hexane acetone was obtained 2.9 g of white crystals, so pl. 150 153oC (decomp.), Thin layer chromatography on silica gel (manifesting the solvent chloroform methanol:water 65 25 4/: Rf0,30).

Elemental analysis for C36H53O12P2H2O

calculated With 58.05 H 7.71

found: 58.37 H 7.85

IR:CVGCVG3432, 2976, 1734, 1608 cm-1.

Example 2

Methyl 3-(1-ascorbyl-2-phosphoryl)-glycyrrhetinic

In 30 ml of dry chloroform was dissolved 5 g of methyl glycyrrhetinate and 8 ml of dry pyridine and to this solution while cooling with ice and stirring was bury 3.2 g of chloride phosphoryla in 30 ml of dry benzene. The resulting mixture was stirred under ice cooling for 30 min and then for 1.5 h at room temperature. Then the reaction mixture was koncentrirebuli under reduced pressure and the residue was dissolved in 20 ml of benzene. This benzene solution was to bury a mixture of 4 g isopropylidenediphenol acid and 2.5 ml of dryCVGpyridine in 30 ml of dry tetrahydrofuran and received the promo mixture was concentrated under reduced pressure. The remaining oil was added 50 ml of ethanol and 20 ml 0,511 hydrochloric acid and the resulting mixture was stirred for 30 min at 60oC to diatonically. After cooling, the reaction mixture was extracted with ethyl acetate and the extract was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. Next, the solvent is kept at reduced pressure. To the residue was added g-hexane, and the mixture was stood and the resulting crystals were collected by filtration and recrystallized from a mixture of n-hexane-acetone to obtain 2.5 g of white crystals, so pl. 135 138oC (decomp. ). Thin layer chromatography on silica gel (TLC) (showing the solvent chloroform methanol: water 65 25 4) Rf0,32.

Elemental analysis for C37H55O12P3H2O

calculated: C, 57.21, H 7.91

found: C at 57.53 H 7.85

IR:CVGCVG3424, 2932, 1730, 1662 cm-1.

Example 3

Ethyl 3-(ascorbyl-2-phosphoryl)-glycyrrhetinic

Repeating the procedure of example 2 using 4.8 g of ethyl glycyrrhetinate and the reaction product was recrystallized from a mixture of n-hexane-acetone to obtain 2.8 g of white crystals, so pl. 130 132oC (decomp.) TLC on silica gel (showing RA22H2O

calculated: C, 59.06 H of 7.96

found: C: 59.34 H: 7.96

IR: :

1. Derivative of glycyrrhetic acid of General formula

< / BR>
where R is hydrogen, unsubstituted or substituted C1-C18-alkyl,

or their pharmacologically acceptable salts.

2. Connection on p. 1, characterized in that it is a 3-(1-ascorbyl-2-phosphoryl)-glycyrrhetic acid.

3. Connection on p. 1, characterized in that it represents methyl 3-(1-ascorbyl-2-phosphoryl)-glycyrrhetinate.

4. Connection on p. 1, characterized in that it represents ethyl 3-(1-ascorbyl-2-phosphoryl)-glycyrrhetinate.

5. Connection on p. 1, characterized in that a represents a hexyl 3-(1-ascorbyl-2-phosphoryl)-glycyrrhetinic potassium.

6. Connection on p. 1, characterized in that it is a lauryl 3-(1-ascorbyl-2-phosphoryl)-glycyrrhetinic potassium.

7. Connection on p. 1, characterized in that it is stearyl 3-(1-ascorbyl-2-phosphoryl)-glycyrrhetinate.

8. The method of obtaining the derivative of glycyrrhetic acid, characterized in that conduct the interaction of glycyrrhetic acid or its Olkiluoto ether galoidovodorodami agent, the linen or chloroform, at a temperature of 0 50oWith the continuation of from 1 to 10 h in the presence of an amine such as pyridine or triethylamine and interact formed compounds with ascorbic acid, previously protected by the provisions of the 5 - and 6-acyl or alkylidene group, in a solvent such as dioxane or tetrahydrofuran at a temperature of 0 50oWith the continuation of from 1 to 10 h in the presence of an amine such as pyridine or triethylamine and subsequent hydrolysis to remove the protective groups in the mixture of water with sadomasichism organic solvent, such as methanol, ethanol, dioxane, tetrahydrofuran, at temperatures from 0 to 60oC for 1 to 2 h in the presence of acid, such as hydrochloric acid, sulfuric acid, phosphoric acid, acetic acid or citric acid.

 

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