Long-chained unsaturated oxidated compounds and their application to areas of therapy, cosmetics, and nutrition

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention relates to application of compounds with formula R2=R1-X, where R1 and R2 have 23 to 35 carbon atoms in sum, X represents primary alcohol functional group -CH2OH or carboxyl group -COOH, R1 is saturated linear hydrocarbon chain with 9 carbon atoms, and R2 is linear hydrocarbon chain, which is saturated or unsaturated, including 1 to 4 unsaturated double links.

EFFECT: producing formulations suited for application to hypercholesterolemia therapy and prophylaxis.

3 cl, 4 tbl, 6 ex

 

The present invention relates to new applications in the field of therapy, cosmetics and nutrition alcohols, acids and esters of these acids with long mono - or polyunsaturated hydrocarbon chain.

New applications and connections forming the subject of the invention is defined in the following claims.

In particular, new applications, which include the invention relate to compounds of the formula R-X, where X represents an optionally converted into a salt of a primary alcohol-CH2HE or carboxyl-COOH functional group or esterified carboxyl group-COOR3where R3represents a C1-C4alkyl, preferably ethyl or propyl (and complex glyceride esters of these acids), and where R represents a hydrocarbon chain having from 19 to 35 carbon atoms, preferably from 23 to 35, and preferably from 25 to 31 carbon atoms and including one or more ethylene or acetylene unsaturated bonds, preferably one to five unsaturated bonds; a hydrocarbon chain preferably R is a linear or optionally branched chain, containing from one to five methyl branches, and the chain may be optionally substituted by one or more hydroxyl groups is, for example from one to three hydroxyl groups.

The invention is also directed to a preferred class of compounds consists of compounds of the General formula R2=R1-X, where X has the meaning indicated above, and where R1and R2have only 23 to 35 carbon atoms, preferably from 25 to 31 carbon atoms, and R1represents a saturated linear hydrocarbon chain having from 4 to 15, preferably from 7 to 13 carbon atoms, and R2represents a hydrocarbon chain having from 8 to 22, preferably from 10 to 20 carbon atoms, which is saturated or unsaturated, comprising from 1 to 4 ethylene or acetylene unsaturated bonds, and preferably a linear or optionally branched, comprising from 1 to 4 methyl branches, and optionally substituted hydroxyl group, for example from 1 to 3 hydroxyl groups.

More preferable compounds, where R1represents a linear saturated hydrocarbon chain having 9 carbon atoms, and compounds, where R2represents a hydrocarbon chain, saturated or unsaturated naturally occurring fatty acids, such as, for example, hydrocarbon chain of oleic, linoleic, linolenic, ricinoleic or farnesiana acid.

Compounds in accordance with the invention, m is should be obtained by synthetic methods, known in the literature, in particular the method described in TOA on behalf of the applicant, the description of which should be considered as included in the present description by reference.

This method involves the reaction of Reinsalu Wittig (see Merck Index, XII ed., ONR-99 and referenced in this reference)in which the phosphorus ylides (R"R(Ar)3), where R" is a saturated or unsaturated hydrocarbon chain comprising one or more ethylene or acetylene unsaturated bonds, and where Ar represents a phenyl - interacts with the n-alanovoy acid R COOH, oxazolidines in the limit position, or complex With1-C4alkilany ether specified oxazolidines alanovoy acid to obtain a product of the merger, consisting of alkinoos acid R"=R'-COOH or its complex Olkiluoto ether (where the term "Allenova" refers to the presence of ethylene ninasimone communication introduced in the reaction of the Wittig), having the desired chain length.

The number of carbon atoms in the group R" above the phosphorus ylides can vary within wide limits, in particular R ' can be the same as defined above, the group R2.

Similarly, the length of the chain R' above n-alanovoy acid, which formulirovka in the limit position, or its complex Olkiluoto ether may be varied within wide the x range and can be selected as a function of position, in which the target connection has the first double bond.

In particular, R' may be the number of carbon atoms corresponding to the definition of R1above, and specifically, may be a 10-octadecanoyl acid or the corresponding 10-octadecanoate lower alkyl (preferably ethyl).

Phosphorus ylides R"P(Ar)3produced by interaction of the corresponding halogen derivative (where halogen represents mainly bromine or chlorine) with triphenylphosphine, preferably in an aromatic solvent (toluene) when heated by boiling under reflux; after the reaction solution was concentrated and the phosphonium salt is precipitated, preferably by a simple ether.

Due to the fact that in the above reaction the Wittig preferably be used as a reagent complex alkilany ether, formirovanii in the limit position n-alanovoy acid, the method leads directly to obtain unsaturated compounds used within the scope of the invention, having a functionality of ester. The corresponding unsaturated acid can be obtained from the complex ester hydrolysis in alkaline medium and the corresponding compounds having a functionality of a primary alcohol, recovery of ester, for example, lithium hydride-aluminum.

The method receiving the Oia compounds, used within the scope of the invention is further illustrated by the following examples.

Example 1. Obtaining complex ethyl ester achacoso-10,19-diene acid

The method of synthesis is illustrated in the following diagram and associated stage of the operations described in the following examples 1a-1d.

NMO: N-oxide N-methylmorpholine.

Example 1A. Complex ethyl ester undecenoic acid

In dvuhholos the flask with a capacity of 100 ml 8 ml of ethanol and collected on the tip of a spatula of the steam-toluensulfonate acid is added to 15 g undecenoic acid (81,4 mmol), dissolved in 35 ml of anhydrous toluene. The contents heated to boiling under reflux for 8 h distillation apparatus Dean - stark or Markusson, separating the water of esterification. All used chemical ware pre-dried in an oven at 120°C. Progress of the reaction is controlled TLC (thin layer chromatography) plate of silica gel), eluent - hexane/EtOAc, 7:3. Rfcomplex ester of 0.67.

Procedure: the product is diluted EtOAc, washed twice with a mixture of NaHCO3/N2About 1:1, then H2Oh, and a saturated solution of NaCl and dried over Na2SO4. Obtain 16.7 g (78,9 mmol) (yield 97%). Any trace amounts of the original acid can be removed by filtering through a layer of aluminum oxide.

Example 1b. 10-Octadecane the t of ethyl

In the flask with a capacity of 500 ml 2.5 ml of 0.2 M solution of OsO4in toluene (0.005 equivalent; 1,03 mmol) and 24,13 g N-methylmorpholin-N-oxide (1 equivalent) are added to 43,67 g complex ethyl ester undecenoic acid (0,206 mmol), dissolved in 100 ml of a mixture (1:1) H2O/acetone. Content left under stirring for 15 min at 0°With ice. Then small portions add 79,31 g NaIO4(1.8 equivalent; and 0.37 mmol) over a period of 40 min at ambient temperature. After interaction should TLC plate of silica gel), eluent - hexane/EtOAc, 7:3. Rfproduct of 0.5.

The procedure of obtaining: the product is filtered on a funnel with a sintered, porous guide wall, diluted EtOAc, washed with saturated NaCl solution and dried over Na2SO4. The product is then purified on a chromatographic column of silica gel (SS), eluent - hexane/EtOAc, 9:1. Get to 38.3 g 10-octadecanoate ethyl (179,2 mmol) (yield 87%).

Example 1C. Fofanova salt of CIS-1-bromo-9-octadecene

In the flask with a capacity of 250 ml of 1 equivalent of triphenylphosphine (24,6 g) are added to 29,8 g of CIS-1-bromo-9-octadecene (0.09 mmol)dissolved in 80 ml anhydrous toluene. The contents heated to boiling under reflux in a heating enclosure within 24 hours It is cooled in a bath of water and ice for about 10 min, and then add about 15 ml simple Dyatlovo the ether. The phosphonium salts deposited in large quantities, and it is filtered on a funnel with a sintered, porous guide wall, and washed with about 50 ml of a simple ester. Gain of 40.9 g pink pearl solids (71,2 mmol). Yield 80%.

Example 1d. Complex ethyl ester achacoso-10,19-diene acid

In dvuhholos the flask with a capacity of 1 liter to 31.9 g of phosphonium salts of (56.0 mmol) was dissolved in 350 ml of anhydrous THF under stirring with a magnetic stirrer under nitrogen atmosphere. All used chemical glassware was pre-dried in an oven at 120°C. 1.05 equivalent of BuLi solution (1.6 M in hexane) (34 ml) is slowly added dropwise; the color of the reaction mixture becomes more orange-red, indicating the formation of ylides. After about 20 min, 5 ml of a solution containing 10,78 g 10-octadecanoate ethyl (0.9 equivalent; and 50.4 mmol) is slowly added dropwise, during the addition of the aldehyde color of the solution becomes yellow-orange. Content left overnight under stirring with a magnetic stirrer. The progress of the reaction is controlled TLC plate of silica gel), eluent - hexane/EtOAc, 9:1. Rf product 0,67.

Procedure: the product is diluted to 0.1 N. HCl solution and extracted with EtOAc; the washing is carried out with a saturated solution of NaCl, and drying carried out over Na2SO4. Get a 20.2 g of the product (45,1 mmol). Output 90%.

Example 2. is chakuza-10,19-diene acid

In the flask with a capacity of 100 ml 5.3g complex ethyl ester achacoso-10,19-diene acid (to 11.8 mmol) in a mixture with water of 3.5 N. NaOH solution (30 ml) is heated at 90°C for 2 h the Progress of the reaction is controlled TLC plate of silica gel), eluent - hexane/EtOAc, 8:2. Rfproduct 0,30.

Procedure: the mixture is acidified with 1 N. HCl and extracted with CH2Cl2. The organic phase is washed with saturated NaCl solution and dried over Na2SO4. Obtain 4.7 g of Akcakoca-10, 19-diene acid (11,2 mmol) Yield 95%.

Example 3. Achacoso-10,19-dienal

As mentioned above, the alcohol can be obtained from complex ethyl ester achacoso-10,19-diene acid (example 1d) recovery, for example, lithium hydride-aluminum.

Example 4. Achacoso-10,19,22-TRINOVA acid

The above acid, its corresponding ester (preferably complex ethyl ester) and the corresponding primary alcohol can be obtained by the procedure described in examples 1-3, using as reagent in the reaction of the Wittig fosfonovoi salt of 1-bromo-9,12-octadecadienyl (a derivative of linoleic alcohol).

Example 5. Achacoso-10,19,22,25-terraenovae acid

The above acid, its corresponding ester (preferably complex ethyl ester) and the corresponding primary alcohol can be obtained following the procedure described in examples 1-3, using as the starting compound in the reaction Wittig fosfonovoi salt of 1-bromo-9,12,15-octadecatrienoic (derived linolenic alcohol).

Example 6. 14,18,22-Trimethylchitosan-10,13,17,21-terraenovae acid

The above acid, its corresponding ester (preferably complex ethyl ester) and the corresponding primary alcohol can be obtained following the procedure described in examples 1-3, using the Wittig reaction fosfonovoi salt of 1-bromo-3,7,11-trimethyl-2,6,10-dodecatrien (derived farnesol).

In General, the described compounds have greater activity than the corresponding policosanol and policosanol acid, and therefore it can with advantage be used in the field of therapy, cosmetology, and food (in particular, as a nutritious diet integrators), which typically use policosanol and policosanol acid.

Described compounds have high antioxidant activity and a high degree of activity in the capture of free radicals, which allows their use in cosmetic and nutritional compositions as antioxidants to prevent associated with oxidation damage of these compositions, and in cosmetic and dermatological compositions for topical application for the prevention and treatment of skin damage caused by free radicals, such as, in particular, the use for the treatment and prevention of the effects on the skin, causing her FOTS the representation and aging.

These compounds are also characterized by higher gipoholesterinemicheskoy and/or hypolipidemic activity in addition to the favorable effect on the picture lipoproteins (increase lipoproteids high-density HDL) compared with the corresponding policosanol; therefore, they are suitable for use in the manufacture of medicaments and pharmaceutical compositions that can be used for the treatment and prevention of pathological conditions associated with hypercholesterolemia and hyperlipidemia, such as, for example, cardiovascular diseases coronary or atherosclerotic type, and peripheral vascular disease, as well as for prevention and treatment of pathological conditions associated with the increased ability of blood platelets aggregated with reduced oxygenation and nutrition of tissues, such as peripheral neuropathy, particularly diabetic peripheral neuropathy.

Described compounds showed high activity in restoring fluidity of cell membranes,"shadows" or blood platelets and in improving the antioxidant defense mechanisms of plasma, liver, brain and heart.

Therefore, pharmaceutical compositions containing these compounds, can be applied in General in the treatment of aging, the key brain aging, and degenerative diseases of the brain such as Alzheimer's disease, Parkinson's disease, senile dementia, memory loss and confused state of consciousness and States of stress and depression.

Another application of the described compounds is a therapeutic treatment and prevention of obesity, and diet compositions, nutritional integrators aimed at weight loss and the prevention and treatment of cellulite.

Described compounds can also be used in the manufacture of compositions nutritional integrators designed to increase muscular strength and suitable for improving physical fitness in humans and animals.

Forms introduction to pharmaceutical compositions and dietary integrators are preferably forms the introduction oral route, such as, in particular, tablets, lozenges and capsules, including carriers and/or excipients which are pharmaceutically acceptable for use in the field of nutrition.

Connections can also be used in the compositions, including other active ingredients, in particular anti-oxidant vitamins, such as vitamin e, lipoic acid, vitamin C, vitamin B6, vitamin B12.

Useful also is the use of the compounds in combination with L-carnitine or its alkanoyloxy derived in particular, in the treatment of the above pathological conditions caused by altered lipid metabolism.

Compounds with acid functionality can be applied in the form of pharmaceutically acceptable salts or in the form of tri-, di - and monoglycerides, esters phospholipids or also in the form of salts with amino acids (such as arginine, lysine, methionine, cysteine and the like).

Hypocholesterolemic activity

The aim of the study is the analysis of the hypocholesterolemic activity of the compounds of octacosanol and octacosanol acid compared to the activity of commercial policosanol natural origin.

The study was performed in male new Zealand white rabbits (Harlan Italy, Correzzana)having a body weight from 1 to 1.3 kg of the Animal was kept in a room with controlled conditions (12-hour cycle of light/dark, relative humidity 60% and temperature of 22° (C) and gave them the standard feed Harlan and water without restrictions.

Rabbits were weighed and randomly distributed into different groups of treatment and control, as shown in table 1. After a week, took blood samples from all animals from the outer marginal vein of the ear and measured the blood levels of cholesterol, triglyceride, HDL cholesterol and LDL cholesterol ("time 0", see table 2).

Table 1

The experimental group
GroupThe number of rabbitsProcessing type
Negative control4The standard ration
The positive control4Hypocholesterolemic diet (D.IP.)
PSIIT4D.IP. + Policosanol S.I.I.T.
PGC4D.IP. + Policosanol Giellepi Chemicals
OLO6D.IP. + Octacosanol
OICO6D.IP. + Octacosanol acid

Hypocholesterolemic diet was prepared in accordance with Menendez et al. (1997) and described by Kroon et al. (1982).

For each experiment, the diet was restricted amount of 100 g/feeding in accordance with the above sources of information.

Animals of the negative control group received standard feed; animals of the positive control group and groups PSIIT, PGC, OLO and OICO stood on hypocholesterolemic diet (D.IP.).

In parallel, animals from groups PSIIT, PGC, OLO and OICO daily for 30 days in a row was treated with the same substances. The compounds were administered orally through a special gastric cannula at a dose of 50 mg/kg of body weight, in the form of what spencie in water/Tween 20 (daily volume, enter each animal, 1 ml/kg body weight/day) (Menendez et al., 1997). Animals of groups of negative and positive controls received an equal volume (1 ml/kg body weight/day) a mixture of water/Tween 20.

It should be clear that the animals of groups PSIIT and PGC received a certain number of policosanol S.I.I.T. of policosanol Giellepi Chemicals with the content of the active substance, which corresponded to the number of octacosanol and octacosanol acid (the compounds).

After 30 days of treatment took blood samples from the outer edge of Vienna and measured the blood levels of cholesterol, triglyceride, HDL cholesterol and LDL cholesterol. The results are presented in table 4.

Rabbits after weighing was slaughtered in accordance with national and international rules by injection (b) pentobarbital sodium (50 mg/ml) and was extracted aorta (from the output of the left ventricle of the heart is approximately 5 mm above the bifurcation of the iliac bone) and placed in 4% formalin for analysis of the presence of atherosclerotic plaques.

Table 2

Hematochemical parameters at the beginning of the processing ("time 0")
Experimental groupCholesterol, mol/lTriglycerides, mol/lHDL, mol/l
CTRL NEGa 1,79±0,411,57±0,430,72±0,22
CTRL POSa1,71±0,351,46±0,220,61±0,19
PSIITa1,89±0,461,57±0,430,79±0,21
PGCa1,70±0,221,67±0,300,65±0,27
OLOb1,85±0,381,61±0,380,70±0,24
OICOb1,73±0,461,50±0,350,81±0,21
The above values are averages ± standard deviation from the 4aor 6bindependent experiments

Table 3

The effect of different treatments on body weight of animals
Experimental groupTime 0 kgTime 30 days, kg
CTRL NEGa1,2±0,31,7±0,3
CTRL POSa1,3±0,21,8±0,2
PSIITa1,1±0,21,6±0,3
PGCa1,1±0,11,7±0,4
OLOb1.2±0.21,7±0,5
OICOb1,0±0,11,6±0,6
The above values are averages ± standard deviation from the 4aor 6bindependent experiments

Table 4

The effect of compounds on hematochemical parameters
Experimental groupCholesterol, mol/lTriglycerides, mol/lHDL, mol/lLDL, mol/l
CTRL NEGa1,87±0,381,66±0,490,67±0,230,53±0,23
CTRL POSa4,27±1,05c1,72±0,380,78±0,220,86±0,38c
PSIITa3,20±0,961,80±0,710,73±0,260,77±0,321
PGCa3,18±1,041,60±0,870,65±0,240,71±0,33
OLOb2,72±0,83d1,79±0,890,77±0,190,69±0,28d
OICOb2,85± 0,82d1,74±0,700,70±0,250,70±0,26d
The above values are averages ± standard deviation from the 4aor 6bindependent experiments
1:ADP was used as an agonist (2.5 Ámol/ml)
cp<0,01 relative to the negative control (Wilcoxon)
dp<0,05 relative to the positive control (Wilcoxon)

Processing in different conditions had no specific effect on the body weight of animals: weight increase during experiments (0,5-0,6 kg) is comparable for different experimental situations.

The data show a surprising effect on LDL cholesterol. Search atherosclerotic plaques gave a negative result as in the positive control group and treated groups D.IP. and the compounds; however, there are suggestions that the levels of cholesterol in the blood that were found (approximately two times higher than the negative control, four weeks), do not indicate the formation of atherosclerotic plaques, so the absence of such plaques is compatible with the results.

The obtained results showed the t, that test compounds (compounds of the present invention, OLO and OICO) have improved cholesterol-lowering effect compared with commercial policosanol.

1. The use of compounds of the formula R2=R1-X, where R1and R2have only 23 to 35 carbon atoms, X represents a primary alcohol functional group,- CH2HE or carboxyl functional group-COOH, R1represents a saturated linear hydrocarbon chain having 9 carbon atoms, and R2represents a linear hydrocarbon chain, which is saturated or unsaturated, comprising from 1 to 4 ethylene unsaturated bonds, to obtain compositions that can be used for the treatment and prevention of hypercholesterolemia.

2. The use according to claim 1, where R2represents a chain saturated or unsaturated naturally occurring fatty acid.

3. The use according to claim 2, where R2represents a hydrocarbon chain of oleic, linoleic, linolenic, ricinoleic or farnesiana acid.



 

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