Glycopeptide of glycirrisine acid with l-prolin humoral immune response stimulating

FIELD: biochemistry.

SUBSTANCE: describes is new chemical compound, namely glycirrisine acid derivative with L-prolin: 3-O-{2-O-[N-(β-O-glucopyranosyluronoyl)-L-prolin-N-(β-D-glucopyranosyluronoyl)-L-prolin]}-(3β,20β)-11-oxoolean-12-en-30-oic acid, stimulating of humoral immune response. Said compound has low toxicity and increases agglutinins levels (by 3,7 times) and hemolysines level (by 3 times) in mouth blood in contrast with control while administrating of 2 mg/kg.

EFFECT: preparation with increased stimulating activity in relation to agglutinin production.

1 cl, 2 ex

 

The invention relates to new biologically active compounds, specifically to glycopeptide glycyrrhizic acid with L-Proline (Pro): 3-O-{2-O-[N-(β-D-glucopyranosyloxy)-L-Proline-N-(β-D-glucopyranosyloxy)-L-Proline]}-(3β, 20β)-11-oxo-Olean-12-EN-30-oeva acid, of the formula (IB)stimulating primary immune response. The specified connection and its properties are not described in literature.

It is known that glycyrrhizin acid (ha) and its derivatives containing fragments of amino acids and their alilovic esters, show together with immunomodulating activity (Gaellic, Loubutin, Eel, Agudosi. Glycyrrhizin acid. // Bioorgan, chemistry, 1997, volume 23, No. 9, s-709; Ramchandran, Loubutin, Chrastava, Navratilova, Himasaram, Gaellic. The method of obtaining crystalline glycyrrhizic acid from industrial glycyram. Immunomodulating properties. // Chem.-Pharm. Zhur., 2001, t.35, No. 2, p.39-42; Liabiltiy, Gamsahurdia, Passarotti, Genesareth, Gaellic, Wagawaga. Synthesis of glycopeptides glycyrrhizic acid and their Immunomodulating properties. // Chem.-Pharm. Zhur., 1990, No. 2, p.119-121; Liabiltiy, Saigawa, Avecilla, Gaellic, Gamsahurdia, Passarotti. Transformation of glycyrrhizic acid. VIII. Synthesis of immunomodulatory glycopeptides using tert-butyl esters of amino acids. // Bio is ran. chemistry, 1994, t.20, No. 12, s-1374).

(1a) R=L-Pro-OBut

(IB) R=L-Pro-OH

(II) R=L-Cys (SBzl)-HE

The task, which directed the claimed technical solution is to search for a new low-toxic compounds in the series of glycopeptides ha with immunostimulatory activity. In the claimed technical solution synthesized a new molecule - glikopeptid Ledger containing residues of L-Proline of the formula (IB), stimulates agglutinins and hemolysins in the serum of mice.

The method of obtaining the proposed connection is that the group treated with N-hydroxysuccinimide (HOSu) and N,N'-dicyclohexylcarbodiimide (DCC) in tetrahydrofuran (THF), at 0-+5°C for 2 h with a ratio of chemicals VOC: HOSu: DCC=1:4:2.5 mmol, filtered off the precipitated N,N'-dicyclohexylmethane, to the filtrate at 0-+5°add 2.5 mmole hydrochloride tert-butyl ester of L-Proline and 3 mmol of triethylamine stir the mixture at this temperature for 1 h and incubated at room temperature for 20 hours

The reaction mixture was diluted with cold water, acidified with citric acid to pH˜4, the precipitate filtered off, washed with water, dried and chromatographic on a column of silica gel (SG). The homogeneous fractions are combined and evaporated. Output protected glycopeptide (Ia) 49,5%.

Protected glikopeptid (Ia) process triperoxonane acid in methylene chloride at room temperature for 1 h, evaporated the solvent and the residue chromatographic on the column with the SG and get to 0.29 g (64,4%) homogeneous by TLC target glycopeptide (IB), the structure of which is confirmed by spectroscopic methods and elemental analysis data.

Acute toxicity of the compound (IB) was studied in outbred mice weighing 15-20 g intraperitoneal injection according to the method of Cerberus (OLGA Elizarova. The determination of threshold doses of industrial poisons when administered orally. M.: Medicine, 1971. P.47-48.). This compound at a dose of up to 950 mg/kg toxic effects not caused and can be classified as class III hazardous substance.

The influence of glycopeptide (IB) on humoral components of the immune response was studied in outbred mice weighing 18-20 g sensitization 3% suspension of sheep erythrocytes (EB). From the first day of sensitization, the animals received the compound (1B) orally in doses of 10 mg/kg (7-day introduction) and 2 mg/kg (10-day introduction). Control animals were injected with saline or a structural analogue with a high immunostimulatory activity, glikopeptid GC with S-benzyl-L-cysteine (II)obtained previously described (Ramchandran, Loubutin, Avecilla, Liabiltiy (ml), Afesmoldova, Himasaram, Njemackom, Rmiia. Synthesis and immunostimulirutuyu activity cysteinaemia glycopeptides derived glizer sinoway acid. // Bioorgan, chemistry, 2004, CH, No. 1, pp.61-67).

A day later the animals by decapitate collected blood serum which was determined by the content of agglutinins and hemolysins according to (VII. The role of chronic gonadotropin, autoantibodies to him and his counterparts in the immune system in health and disease. Diss. Dr. med. of Sciences, Kazan, 1990. P. 346). Response was assessed using Log2 titers of antibodies - hemagglutinin and hemolysins. The results of the experiments are shown in the table.

As can be seen from the table, the compound (IB) after 7 days at a dose of 10 mg/kg significantly increases the level of agglutinins and hemolysins compared with the control (3.7 times and 3 times respectively). To 14-th day the title of agglutinins in the group of animals receiving the compound (IB) in the dose of 2 mg/kg, was higher in 4 times, and the titer of hemolysins 2.5 times compared with the control animals, which received inside saline. The compound (IB) by stimulating activity in the production of agglutinins exceeds the reference product (II) ˜ 2 times at a dose of 2 mg/kg at 14-day introduction and does not yield him to the stimulating effect on the production of hemolysins in both the studied doses.

Thus, the compound (IB) is a toxic compound that has a strong stimulating effect on the humoral components of the immune response and exceeds what about the immunostimulatory activity of the structural and pharmacological analogue - glikopeptid GC (II) (reference drug).

The invention is illustrated by the following examples.

Example 1. The influence of glycopeptide (IB) on humoral components of the immune response.

The influence of glycopeptide (IB) on humoral components of the immune response was studied in outbred mice weighing 18-20, the Experiments were conducted on 3 groups of animals (14 mice in each group, divided into 2 subgroups based on 7 mice) sensitization of mice with 3% suspension of erythrocytes master (DL) 0.5 ml per mouse (intraperitoneal). From the first day of sensitization, the animals received an investigational compound orally in doses of 10 mg/kg (7 day introduction) and 2 mg/kg (14-day introduction). Control animals were injected inside saline. As the comparison drug used glikopeptid GC with S-benzyl-L-cysteine (II) at doses of 10 and 2 mg/kg, described in (Ramchandran, Loubutin, Avecilla, Liabiltiy (ml), Afesmoldova, Himasaram, Njemackom, Rmiia, Gaellic. Synthesis and immunostimulirutuyu activity cysteinaemia glycopeptides derived glycyrrhizic acid. // Bioorgan, chemistry, 2004, CH, No. 1, pp.61-67).

On the 7th and 14th day sensitization mice each subgroup subplantar in his right claw was introduced allowing the dose of EB at a concentration of 108; the other foot remained intact. A day later the animals by Dec is pitali collected blood, in serum, which was determined by the content of agglutinins and hemolysins in methodology (VII. The role of chronic gonadotropin, autoantibodies to him and his counterparts in the immune system in health and disease. Diss. Dr. med. of Sciences, Kazan, 1990. P. 346). Response was assessed using Log2 antibody titer - hemagglutinin and hemolysins. The results of the experiments are shown in the table.

The compound (IB) in the dose of 10 mg/kg at 7-day introduction statistically significantly increases the titer of agglutinins and hemolysins respectively 3.7 and 3-fold compared with control. When 14-day dose of 2 mg/kg titer agglutinins in the group of animals receiving the compound (IB) was 4 times higher, and the titer of hemolysins 2.5 times compared with the control. Thus, glikopeptid (IB) ˜ 2 times greater than the reference drug glikopeptid (II) promotion agglutinins at a dose of 2 mg/kg and not inferior to the latter stimulating activity on the production of hemolysins.

Example 2. Synthesis of 3-O-{2-O-[N-(β-D-glucopyranosyloxy)-L-Proline-N-(β-D-glucopyranosyloxy)-L-Proline]}-(3β, 20β)-11-oxo-Olean-12-EN-30-oewoi acid (IB).

1. To a solution of 0.82 g (1 mmol) of glycyrrhizic acid in 20 ml of dry THF at 0-+5°was added 0.46 g (4 mmol) of N-hydroxysuccinimide, 0.5 g (2.4 mmol) of N,N'-dicyclohexylcarbodiimide and stirred at this temperature for 2 hours the precipitated N,N'-what ziklogexilovy was filtered, to the filtrate at 0-+5°With added 0,58 g (2.5 mmol) of the hydrochloride tert-butyl ester of L-Proline and 0.5 ml (3.6 mmol) of triethylamine, the mixture was stirred at this temperature for 1 h and was kept for 20 h at room temperature with periodic mixing. The reaction mixture was diluted with water, acidified with citric acid to pH˜4, the precipitate was filtered, washed with water and dried. The product (1.0 g) was chromatographically on a column of silica gel L (40/100 μm), elwira mixture of chloroform-methanol-water, 300:10:1, 200:10:1 and 100:10:1 (V%). A mixture of 200:10:1 was washed 0.55 g (49,5%) protected glycopeptide (Ia), homogeneous by TLC. Rf=0,54 (chloroform-methanol-water, 45:10:1). The IR spectrum νcm-1: 3600-3200 (HE, NH); 1730 (COOR); 1710 (COOH); 1660 (C=O); 1540 (CONH). UV-spectrum λmax(MeOH) (lg ε): 250 nm (4,1). Found, %: N 2,58. C60H91N2O17. Calculated, %: N, 2,52. Mr=1112,34.

2. 0.5 g (0.45 mmol) of the protected glycopeptide (Ia) has stood for 1 h in a mixture of 10 ml triperoxonane acid and 10 ml of methylene chloride. The residue after evaporation of the solvents was chromatographically on a column of silica gel, elwira mixture of chloroform-methanol-water, 100:10:1, 50:10:1 (V%). The output of glycopeptide (IB) of 0.29 g (64.4 per cent). Rf=0,48 (chloroform-methanol-water, 45:10:1), [α]D20+45°With (from 0.02; MeOH). The IR spectrum νcm-1: 3600-3200 (HE, NH); 1710-1720 (COOH); 1660 (C=O). UV-spectrum λmax(MeOH) (lg ε): 250,5 nm (4,05). Neid is but %: N 2,82. C52H75N2O17. Calculated, %: N 2,80. Mr=1000,13. An NMR spectrum13(CD3OD, δ, ppm): 40,3 (C1); 90,9 (C3); 56,5 (C5), and 33.8 (C7); 63,2 (C9); 202,5 (C11); 128,9 (C12); 168,9 (C13); 27,4 (C15); 32,9 (C17); 42.5 (C19); 32,0 (C21); of 180.5 (C30); 105,4 (C1'); 83,8 (C2'); 75,7 (C3'); 72,4 (C4'); 77,3 (C5'); 172,7 (C6'); 106,1 (C1"); 74,8 (C2"); 75,1 (C3"); 72,2 (C4); 77,6 (C5"); 172,9 (C6"). The remains of L-Proline: 175,0; 173,2; 61,7; 61,3; 30,2; 30,1; 25,8; 25,6; 44,9; 44,6.

Table
The influence of glycopeptide (IB) on the level of agglutinins and hemolysins in sensitized mice
ConnectionAfter 7 days (10 mg/kg)After 14 days (2 mg/kg)
Agglutinin (Log2)
(IB)1,50±0,22*3,40±0,10*
(II)1,00±0,20*1,75±0,10*
Control0,40±0,240,80±0,20
The hemolysins (Log2)
(IB)1,20±0,20*1,90±0,10*
(II)1,00±0,10*1,30±0,10*
Control0,40±0,300,75±0,30
*p<0,05 (significantly relative to control)

Glick is a peptide glycyrrhizic acid with L-Proline of the formula

R=L-Pro-OH,

stimulating the humoral immune response.



 

Same patents:

FIELD: natural substances technology.

SUBSTANCE: method of preparing extractive substances from ground birch bark comprises extraction and filtration of precipitated extract. Extraction is effected with extractant condensate sprinkling ground birch bark bed in presence of ascending vapors of the same extractant. Extractant is two-component mixture of water and low-boiling solvent having boiling point below 100°C. Product is isolated by bringing extractant condensate containing dissolved extract with contents of receiver. Once extraction is completed, solvent is removed with live steam.

EFFECT: reduced consumption of extractant, increased degree of extractant regeneration, simplified isolation of product, and reduced fire and explosion risk.

1 tbl, 2 ex

FIELD: fine organic synthesis, in particular production of triterpene compounds, betulin, useful in pharmaceutical and cosmetic industry.

SUBSTANCE: betulin is isolated from birch bark by extraction with neutral organic solvents, namely dioxan aqueous solution containing 0-20 mass % of water.

EFFECT: accelerated extraction process, increased yield of target product, decreased concentration of ester contaminants, and simplified betulin purification.

1 cl, 7 ex, 1 tbl

FIELD: organic chemistry of steroids, chemical technology.

SUBSTANCE: invention relates to the improved method for preparing chemical compounds of steroid order, namely, to a method for preparing epibrassinolide representing (22R,23R,24R)-2α,3α,22,23-tetrahydroxy-B-homo-7-oxa-5α-ergostane-6-one and relating to biologically active substance - a phytostimulator regulating growth of plants. Method involves the successive carrying out the following stages: a) synthesis of ergosterol mesylate by treatment of ergosterol with methanesulfochloride in pyridine; b) synthesis of isoergosterol by boiling ergosterol mesylate in aqueous acetone in the presence of potassium (sodium) hydrocarbonate; c) synthesis of isoergosterone by oxidation of isoergosterol with chrome anhydride in pyridine; d) synthesis of 7,8-dihydroergosterol by reduction of isoergosterone with sodium dithionite in the presence of a solubilizing medium containing cationic, anionic or nonionic surface-active substances of the following order: CnH2n+1X wherein n = 9-18; X means -NMe3, -NEt3, -COOH, -SO3H, -OSO2M, -OP(O)(OM)2 wherein M means alkaline metal, polyethylene glycol, (C2-C6)-aliphatic alcohols or monoesters of ethylene glycol or diethylene glycol as a co-solubilizing agent, electrolyte and water taken in the molar ratio = 1:(5-6):(100-250), respectively; e) steroid rearrangement of 7,8-dihydroisoergosterol; f) formation of 24-epicastasterone by treatment of (22E,24R)-5α-ergosta-2,22-diene-6-one with methanesulfoneamide and potassium carbonate with using catalytic amounts of potassium ferricyanide (III) and osmium tetraoxide; g) dissolving 24-epicastasterone formed in chloroform followed by treatment with trifluoroperacetic acid forming in mixing trifluoroacetic anhydride and hydrogen peroxide in chlorinated organic solvent, and isolation of the end product of the formula (I) with high yield.

EFFECT: improved preparing method.

2 cl, 7 ex

FIELD: chemistry of natural compounds, chemical technology, pharmaceutical industry.

SUBSTANCE: invention relates to the improved method for preparing betulinic acid from betulonic acid. Method is carried out by reduction of betulonic acid with sodium boron hydride in water. Method provides simplifying the process, declining cost of the process for preparing betulinic acid and enhancing ecological safety of the process. Invention can be used in producing antitumor and anti-HIV medicinal preparations.

EFFECT: improved preparing method.

1 cl, 2 ex

FIELD: natural compounds, chemical technology.

SUBSTANCE: invention relates to the improved method for preparing biologically active substances from products of chemical processing vegetable biomass, in particular, to a method for preparing betulinic acid from betuline. Method is carried out by oxidation of betuline with chrome anhydride in acetic acid to betulonic acid, and reduction of betulonic acid with sodium boron hydride is carried out in diethyl ether solution being without its preliminary isolation. Invention provides enhanced yield, simplifying technology, decrease of the process time and decreasing set of solvents used.

EFFECT: improved preparing method.

1 cl, 1 ex

FIELD: medicine; pharmaceutical industry; perfumery-cosmetic industry; methods production of betulin.

SUBSTANCE: the invention is pertaining to the method of extraction of betulin from the wastes products of wood-processing, in particular, a birch bark processing and may be used in medicine, pharmaceutical and perfumery-cosmetic industries. The method provides for activation of a birch bark by the shock-acoustic impulses, an alkaline hydrolysis and an extraction of betulin by an alcohol. The operations are conducted simultaneously. The technical result of the invention is simplification of the method of the process, reduction of its duration and power input.

EFFECT: the invention ensures simplification of the method of the process, reduction of its duration and power input.

1 cl, 2 ex

FIELD: chemical technology.

SUBSTANCE: invention relates to methods for preparing oleanolic acid used as a standard sample (comparison samples) in carrying out standardization of medicinal vegetable raw and phytopreparations comprising triterpene saponins - derivatives of oleanolic acid. For preparing oleanolic acid method involves sum of saponins extracted by alkaline extraction from sugar or table beet root crops followed by reprecipitation in acid medium and extraction of precipitate with ethanol, chloroform. Method provides preparing oleanolic acid of high purity degree from inexpensive and available raw.

EFFECT: improved preparing method.

2 cl, 3 ex

FIELD: chemical technology, natural materials, medicine, pharmacy.

SUBSTANCE: invention relates to the improved method for preparing betulin from betulinic acid that can be used in preparing anti-tumor and anti-HIV medicinal preparations. Method for preparing betulinic acid involves oxidation of betulin with chrome (VI) oxide in acetic acid to betulonic acid and reduction with sodium boron hydride to betulinic acid. Betulonic acid sodium salt is reduced to betulinic acid and reduction reaction is carried out at room temperature at the concentration of sodium boron hydride 1.0-6.0 wt.-%. Invention provides simplifying method for preparing betulinic acid, reducing its cost and enhancing ecological safety of the process of it producing.

EFFECT: improved preparing method.

1 cl, 4 ex

The invention relates to new biologically active compounds, namely diglyceride glycyrrhizic acid methyl ester L-valine of formula (I), stimulating primary immune response

FIELD: natural substances technology.

SUBSTANCE: method of preparing extractive substances from ground birch bark comprises extraction and filtration of precipitated extract. Extraction is effected with extractant condensate sprinkling ground birch bark bed in presence of ascending vapors of the same extractant. Extractant is two-component mixture of water and low-boiling solvent having boiling point below 100°C. Product is isolated by bringing extractant condensate containing dissolved extract with contents of receiver. Once extraction is completed, solvent is removed with live steam.

EFFECT: reduced consumption of extractant, increased degree of extractant regeneration, simplified isolation of product, and reduced fire and explosion risk.

1 tbl, 2 ex

FIELD: fine organic synthesis, in particular production of triterpene compounds, betulin, useful in pharmaceutical and cosmetic industry.

SUBSTANCE: betulin is isolated from birch bark by extraction with neutral organic solvents, namely dioxan aqueous solution containing 0-20 mass % of water.

EFFECT: accelerated extraction process, increased yield of target product, decreased concentration of ester contaminants, and simplified betulin purification.

1 cl, 7 ex, 1 tbl

FIELD: chemistry of natural compounds, chemical technology, pharmaceutical industry.

SUBSTANCE: invention relates to the improved method for preparing betulinic acid from betulonic acid. Method is carried out by reduction of betulonic acid with sodium boron hydride in water. Method provides simplifying the process, declining cost of the process for preparing betulinic acid and enhancing ecological safety of the process. Invention can be used in producing antitumor and anti-HIV medicinal preparations.

EFFECT: improved preparing method.

1 cl, 2 ex

FIELD: natural compounds, chemical technology.

SUBSTANCE: invention relates to the improved method for preparing biologically active substances from products of chemical processing vegetable biomass, in particular, to a method for preparing betulinic acid from betuline. Method is carried out by oxidation of betuline with chrome anhydride in acetic acid to betulonic acid, and reduction of betulonic acid with sodium boron hydride is carried out in diethyl ether solution being without its preliminary isolation. Invention provides enhanced yield, simplifying technology, decrease of the process time and decreasing set of solvents used.

EFFECT: improved preparing method.

1 cl, 1 ex

FIELD: medicine; pharmaceutical industry; perfumery-cosmetic industry; methods production of betulin.

SUBSTANCE: the invention is pertaining to the method of extraction of betulin from the wastes products of wood-processing, in particular, a birch bark processing and may be used in medicine, pharmaceutical and perfumery-cosmetic industries. The method provides for activation of a birch bark by the shock-acoustic impulses, an alkaline hydrolysis and an extraction of betulin by an alcohol. The operations are conducted simultaneously. The technical result of the invention is simplification of the method of the process, reduction of its duration and power input.

EFFECT: the invention ensures simplification of the method of the process, reduction of its duration and power input.

1 cl, 2 ex

FIELD: organic chemistry, steroids, chemical technology.

SUBSTANCE: invention describes a method for preparing 3-keto-7α-alkoxycarbonyl-substituted ▵4,5-steroid of the formula (I): wherein is taken among or R3 means hydrogen atom (H), lower alkyl, lower alkoxy-group or cyano-group (CN); R21 means hydrogen atom (H) or alkyl; R26 means (C1-C4)-alkyl; R8 and R9 form in common heterocyclic ring system. Method involves interaction of an alkylating agent with 4,5-dihydro-5,7-lactone steroid of the formula (II): wherein R18 means (C1-C4)-alkyl or R18O-group taken in common form O,O-oxyalkylene bridge or keto-group and R3, R8 and R9 have above given values in the presence of a base. Compounds of the formula (I) are used as intermediate compounds in improved methods for synthesis of epoxymexerone.

EFFECT: improved preparing method.

56 cl, 42 tbl, 30 sch, 5 dwg, 89 ex

FIELD: chemical technology.

SUBSTANCE: invention relates to methods for preparing oleanolic acid used as a standard sample (comparison samples) in carrying out standardization of medicinal vegetable raw and phytopreparations comprising triterpene saponins - derivatives of oleanolic acid. For preparing oleanolic acid method involves sum of saponins extracted by alkaline extraction from sugar or table beet root crops followed by reprecipitation in acid medium and extraction of precipitate with ethanol, chloroform. Method provides preparing oleanolic acid of high purity degree from inexpensive and available raw.

EFFECT: improved preparing method.

2 cl, 3 ex

FIELD: organic chemistry, steroids, medicine, pharmacy.

SUBSTANCE: invention relates to steroid compounds of the formula (1)

wherein --- means optional double bonds; R6 means hydrogen atom (H), =CH, -CH3 or -CH2-CH3; R7 means hydrogen atom (H), (C1-C4)-alkyl, (C2-C5)-alkenyl, or (C2-C5)-alkynyl; R11 means hydrogen atom (H), (C1-C4)-alkyl, (C2-C4)-alkenyl, (C2-C4)-alkynyl, (C1-C4)-alkylidene; E means 5-7-memberd ring formed with 16 and 17 carbon atoms at α,cis-position relatively to steroid structure and comprising possibly up to two double bonds. Compounds can be used in therapy and in methods for selective modification of activity of estrogen receptors.

EFFECT: improved method for modifying, valuable medicinal properties of compounds.

10 cl, 1 sch, 1 tbl, 1 ex

FIELD: chemical technology, natural materials, medicine, pharmacy.

SUBSTANCE: invention relates to the improved method for preparing betulin from betulinic acid that can be used in preparing anti-tumor and anti-HIV medicinal preparations. Method for preparing betulinic acid involves oxidation of betulin with chrome (VI) oxide in acetic acid to betulonic acid and reduction with sodium boron hydride to betulinic acid. Betulonic acid sodium salt is reduced to betulinic acid and reduction reaction is carried out at room temperature at the concentration of sodium boron hydride 1.0-6.0 wt.-%. Invention provides simplifying method for preparing betulinic acid, reducing its cost and enhancing ecological safety of the process of it producing.

EFFECT: improved preparing method.

1 cl, 4 ex

FIELD: organic chemistry, steroids, pharmacy.

SUBSTANCE: invention describes unsaturated 14,15-cyclopropanoandrostanes of the general formula (I):

wherein R1 means hydrogen atom (H), hydroxy-group (OH); R2 means hydroxy-group (OH), hydrogen atom (H); R3 means hydrogen atom (H), (C1-C10)-alkyl at α- or β-position; R4 means halogen atom (F, Cl, Br) or pseudohalogen group (azide, rhodanide), hydroxy-group (OH), perfluoroalkyl; R5 means (C1-C4)-alkyl; if double bond is at 1,2-position then R4 can mean hydrogen atom (H). Also, invention relates to a method for preparing these compounds and pharmaceutical compositions containing these compounds. Compounds of the formula (I) are compounds eliciting gestagenic and/or androgenic effect.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

11 cl, 1 tbl, 9 ex

FIELD: organic chemistry, steroids, pharmacy.

SUBSTANCE: invention describes unsaturated 14,15-cyclopropanoandrostanes of the general formula (I):

wherein R1 means hydrogen atom (H), hydroxy-group (OH); R2 means hydroxy-group (OH), hydrogen atom (H); R3 means hydrogen atom (H), (C1-C10)-alkyl at α- or β-position; R4 means halogen atom (F, Cl, Br) or pseudohalogen group (azide, rhodanide), hydroxy-group (OH), perfluoroalkyl; R5 means (C1-C4)-alkyl; if double bond is at 1,2-position then R4 can mean hydrogen atom (H). Also, invention relates to a method for preparing these compounds and pharmaceutical compositions containing these compounds. Compounds of the formula (I) are compounds eliciting gestagenic and/or androgenic effect.

EFFECT: improved preparing method, valuable medicinal properties of compounds.

11 cl, 1 tbl, 9 ex

Up!