Perfluorinated cycle-containing tertiary amines as base of gas-transferring emulsions (variants) and method for their preparing

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention relates to novel perfluorinated cycle-containing tertiary amines of the general formula (1): wherein n = 1; m = 2 or 3; X means or and to a mixture of perfluorinated cycle-containing tertiary amines of the general formula (1) wherein n = 1; m = 2 or 3; X means or where at n = 1 Y means CF3 and at n = 2 Y means F as a base for gas-transferring emulsions. Proposed compounds are similar by their physicochemical properties, in particular, by critical temperature dissolving in hexane. Properties of these compounds provide the improved homogeneity of fluorocarbon phase of emulsions and to enhance stability of emulsion particles stabilized with block-copolymer of ethylene oxide and propylene oxide and in the absence of toxicity for small and large animals. Also, invention relates to a method for preparing perfluorinated cycle-containing tertiary amines of the general formula (1) by electrochemical fluorination of p-piperidinoheptafluorotoluene in anhydrous hydrogen fluoride.

EFFECT: improved preparing method and valuable properties of compounds.

4 cl, w dwg, 3 tbl, 4 ex

 

The technical field to which the invention relates.

The invention relates to the field of chemistry of organofluorine compounds and pharmaceutical chemistry, and more specifically to a group of new perforated cycloderma tertiary amines (PFCT). The most effective invention can be used as the basis for creating getparentdir environments, intended for preservation of organs, cruiseline and treatment of pathologies associated with impaired regional blood flow.

The level of technology

Known perfluorinated cyclic tertiary amine PERFLUORO-N-(4-methylcyclohexyl)-piperidine, which has the following formula

with lipophobia properties and used as the basis getparentdir environments, both independently and in combination with lipophilic performancesee compounds (PFOS), such as perftordekalina (PFD) [see Shivarobin, Grievance, Centacare, VMS, Vpechatleno // Perfluorocarbon emulsions stabilized by nonionic copolymers. // In Proc. "Perfluorocarbon active medium for medicine and biology (new aspects of research)" Pushchino, 1993, pp.33-46].

In the description of the invention to the patent of Russian Federation №2088217, published in bull. "Inventions... (s...)" No. 24, 27.08.1998, it is shown that the introduction of the lipophilic fluorocarbon f the s emulsion lipofuze PFCT PERFLUORO-N-(4-metacyclogenesis)-piperidine ensure the elimination of emulsions toxicity for large animals, typical getparentdir emulsions containing lipophilic bistabilities PFOS. However, all the positive properties of the emulsions obtained on the basis of lipophilic PFOS and lipofuze PERFLUORO-N-(4-methylcyclohexyl)-piperidine, particles such emulsions are stable enough. Their instability during freezing-thawing during storage and when released into the bloodstream due, according to the calculations and model experiments [Grivance, Shivarobin, Dev // "Life" of perfluorocarbon emulsions. // In Proc. of "Physiological activity of fluorine-containing compounds (experiment and clinic)" Pushchino, 1995, pp.5-32], the fact that significantly different lipophilicity of PFOS, in particular the critical temperature of dissolution in hexane, formed in the fluorocarbon phase heterogeneous clustered structure characterized by a constant turbulent motion inside the particle emulsion, impairing the stability of the adsorption layer of the surface-active component.

In addition, the use of individual PERFLUORO-(4-methylcyclohexyl)-piperidine hindered due to the high complexity of its receipt and the associated high cost of this connection. All this imposes significant restrictions on the receipt of this substance on an industrial scale and widespread use getparentdir with the ed for biomedical application.

The invention

The task of the invention to provide a new perfluorinated cycloderma tertiary amines with similar physico-chemical and biological properties to PERFLUORO-N-(4-methylcyclohexyl)-piperidine, not toxic for large animals and improving the stability of emulsions by freezing-thawing and released into the bloodstream.

Another object of the invention is the simplification and acceleration of technological process of obtaining PFCT suitable for use as the basis for the production of getparentdir environments and which has an improved range of useful properties.

The task is solved by the fact that as the basis for getparentdir emulsions are encouraged to use the group of perfluorinated cycloderma tertiary amines of General formula (1)

(the value of X and n, see below).

This group of compounds receive electrochemical fluorination of p-piperidinemethanol. This group contains compounds with similar physicochemical properties that determine their successful application in the mix:

two isomer performatives(Methylcyclopentane)amine,

- CIS/TRANS-performatives(4-methylcyclohexyl)amine,

- performativity-(4-methylcyclohexyl)amine,

- CIS/TRANS-PERFLUORO-N-(4-methylcyclohexyl)-2-m is tiliroside,

- CIS/TRANS-PERFLUORO-N-(4-methylcyclohexyl)-piperidine.

A critical parameter that determines the possibility of using the products of the electrochemical fluorination of p-piperidinemethanol is the lack of adaptirovannyh products - hydrogen or of unsaturated compounds causing toxicity. The parameters of the toxicity of individual PERFLUORO-N-(4-methylcyclohexyl)-piperidine and the mixture PFCT almost the same as in the form of liquids, and in the composition of the emulsions (table 1, 2).

All connections of this group PFCT close lipophilic-lipophobia properties and the critical temperature of dissolution in hexane (CTRG in the range of 34-36°by dissolving 25 mol.%). In the mix they form a series of compounds with graduale changing characteristics. Due to this it is possible to achieve greater uniformity fluorocarbon phase of the emulsions obtained on the basis of only this group of compounds and their combination with lipophilic performancesee compounds, and thereby improve the stability of the adsorption layer of the particles of the emulsion, stabilized by blockcopolymers ethylene oxide and propylene oxide (table 3). The emulsion obtained on the basis of group PFCT, as well as emulsions containing individual PERFLUORO-N-(4-metacyclogenesis)-piperidine, not toxic for large animals (tab is .2). In addition, they have the best combination of properties, manifested in greater stability of the resulting emulsions (table 3). All this allows to use them as perfusion environments and blood composition.

Electrochemical fluorination is carried out in the electrolyzer, where to download the electrolyte containing 10-25% of the original p-piperidinemethanol in anhydrous hydrogen fluoride. The temperature of the support in the range of 20-25°C. a current Density ranging from 200 to 400 a/m2when the voltage of 5-6 C. the Process is carried out in 10-12 hours with periodic replenishment of the reaction mixture more concentrated solution of the original substance in anhydrous hydrogen fluoride. Depending on the reaction conditions, the yield of products of the fluorination is from 61 to 78% of the original product. After removal adaptirovannyh (hydrogen and unsaturated) products get a number of perfluorinated cycloderma tertiary amines with a boiling point in the range 179-196°C.

All compounds identified by the methods of gas chromatography-mass spectroscopy and NMR spectrometry. The main compound of this group is CIS/TRANS-PERFLUORO-N-(4-metacyclogenesis)-piperidine (yield 60 to 70%). Other PFCT are products of partial decomposition and isomerization of the original substance in the process of electrochemical fluorine is in the interim. Changes in the percentage of compounds in the mixture PFCT by varying the content of CIS/TRANS-PERFLUORO-N-(4-methylcyclohexyl)-piperidine in the range from 60 to 70% is not affected by any significant way on the physico-chemical and biological parameters of the resulting emulsions. The drawing shows a typical chromatogram obtained perfluorinated cycloderma tertiary amines (capillary column, squalane, 100 m).

Describes the process of obtaining PFCT much easier and cheaper than getting individual pure PERFLUORO-N-(4-methylcyclohexyl)-piperidine, in whatever way it did not receive, because it does not require such time-consuming procedures such as preparative chromatography and distillation. In the literature a method of obtaining individual PERFLUORO-N-(4-methylcyclohexyl)-piperidine not described. However, according to our estimates, the exception process is inevitable when selecting individual products operations preparative chromatography and distillation makes it easier, faster and cheaper process several times.

This mixture PFCT used instead of individual PERFLUORO-N-(4-methylcyclohexyl)-piperidine for cooking getparentdir emulsions. A simplified process reduces the cost of production of PFOS and thereby reduce the cost of production of the gas is enosawa environments while increasing stability and rheological properties of these environments. All this opens up opportunities for industrial production and wider use of emulsions performancesin compounds in research and clinical practice.

Thus, the first object of the invention is perforated cyclododecane tertiary amines of General formula (1)

where n=1; m=2 or 3;

X isor

as a basis getparentdir emulsions.

Preferably such compounds are perfluorinated cyclododecane tertiary amines of General formula (1), selected from the group consisting of CIS/TRANS isomers: performativity(Methylcyclopentane)amine; performativity-(4-methyl-cyclohexyl)amine; performativity-(4-methylcyclohexyl)amine and PERFLUORO-N-(4-methylcyclohexyl)-2-methylpyrrolidine.

Another object of the invention is a method for perfluorinated cycloderma tertiary amines of General formula (I)

where n=1; m=2 or 3;

X isor

where n=1 Y=CF3and when n=2 Y=F,

electrochemical fluorination of p-piperidinemethanol in anhydrous hydrogen fluoride.

Another object of the invention is a mixture of perfluorinated CEC is Osterreich tertiary amines of General formula (I)

where n=1; m=2 or 3;

X isor

where n=1 Y=CF3and when n=2 Y=F,

as a basis getparentdir emulsions.

A brief description of the drawing, which shows a chromatogram of the mixture of perfluorinated cycloderma tertiary amines (capillary column, squalane, 100 m), showing the amplitude of the temperature shift, defined using cataromance sensor, depending on the time of the release of the substance:

peak 1 - two isomer performatives(Methylcyclopentane)amine,

peak 2 - CIS/TRANS-performatives(4-methylcyclohexyl)amine,

peak 3 - performativity-(4-methylcyclohexyl)amine,

peak 4 - CIS/TRANS-PERFLUORO-N-(4-methylcyclohexyl)-2-methylpyrrolidine,

peak 5 - CIS/TRANS-PERFLUORO-N-(4-methylcyclohexyl)-piperidine.

Hereinafter the invention will be illustrated by examples from obtaining specific PTCA. These examples are intended only to confirm the availability of the invention and may not be used to limit the claims of the applicant, reflected in the claims.

Example 1. Getting perfluorinated cycloderma tertiary amines.

In the cell volume of 2 l with external circulation of the electrolyte, equipped with Nickel electrodes with the area of 3000 cm2 download 1500 ml of an electrolyte containing 10% n-piperidinemethanol in anhydrous hydrogen fluoride. The process of electrochemical fluorination is carried out at a temperature of 22°and an initial current density of 200 a/m2and the voltage of the 5th Century was Periodically added to the electrolyte containing 60% solution of p-piperidinemethanol in anhydrous hydrogen fluoride. Within 10 hours of fluoridation, the current density is gradually increased up to 400 a/m2by increasing the voltage until the 6th Century Just passed 800 Ah current and injected into the reaction 330 g of p-piperidinemethanol. Liquid products of the fluorination is separated from the electrolyte, washed with water and sodium bicarbonate solution to remove HF. After removal adaptirovannyh impurities, the mixture of products of the fluorination is distilled. The output of 388 g (61%) of fully fluorinated compounds having a boiling point in the range 179-196°C. In the composition of the obtained completely fluorinated tertiary cycloderma amines according to NMR spectroscopy and mass spectrometry are five types of compounds: 1-isomers performatives(Methylcyclopentane)amine (1%), 2-CIS/TRANS-performatives(4-methylcyclohexyl)amine (2%), 3-performativity-(4-methylcyclohexyl)amine (8%), 4-CIS/TRANS-PERFLUORO-N-(4-methylcyclohexyl)-2-methylpyrrolidine (25%), 5-CIS/TRANS-PERFLUORO-N-(4-methylcyclohexyl)-piperidine (64%) (see chromatogram).

Example 2. Application PFCT.

Obtained in example 1 fully fluorinated products used for the preparation of submicron emulsion containing 10 vol.% PFCT, 3 wt.% block copolymer of ethylene oxide and propylene oxide and an aqueous solution of salts, isotonic plasma (120 mm NaCl, 10 mm NaHCO3, 2 mm KN2PO4, 5 mm KCl 1.2 mm CaCl2), with 10 mm glucose, 1 mm sodium succinate, 1 mm sodium pyruvate, 1 mm 2-hydroxybutrate sodium (pH perfusion solution 7,40). Using the resulting emulsion in recirculating normothermal mode was perfesional isolated kidney of the dog at the rate of 1 l perfusion solution of 40 g of kidney. The vital functions of the body supported within 24 hours after perfusion composition every 6 hours, without the effects of damage to cell membranes (without edema, without a significant increase of resistance of the capillaries, while maintaining the pH of the perfusion solution and without falling rate of oxygen consumption).

Example 3. Application PFCT.

The mixture obtained according to example 1 PFCT with perftordekalina in the ratio of 1:2 is used for the preparation of submicron emulsion containing 10 vol.% fluorocarbon phase, 4 wt.% blockcopolymer ethylene oxide and propylene oxide and an aqueous solution of salts, isotonic plasma (120 mm NaCl, 8 mm NaHCO3, 1.2 mm KN2PO4, 5 mm KCl, 10 mm glucose. The resulting emulsion is used for isovolemic the th cruisemate 65% of circulating blood volume in 10 rats, under General anesthesia with premedication prior, when applying for breathing animals oxygen-enriched air during the operation and in the first day after cruiseline. All animals undergoing cruiseline, survived.

Example 4. Application PFCT.

PFCT mixed with perftordekalina used to produce submicron emulsion as described in example 3. The resulting emulsion at a dose of 20 ml per 1 kg administered intravenously 10 rabbits weighing 2,5-3,5 kg Deviation of body temperature in rabbits after injection of the emulsion does not exceed 0,3°C. there were No signs of allergic reactions. The content of leukocytes in the peripheral blood was decreased by no more than 5% from the original, which also indicates the lack of reactogenicity of the drug. All rabbits had survived the critical period of 80 days (the period during which kill all the rabbits, if they entered emulsion pure performanceline). During the entire observation period (>1 year) any pathological abnormalities in animals is not marked.

Table 1

Comparison of toxicity* individual PERFLUORO-N-(4-methylcyclohexyl)-piperidine (PFMRP) and a mixture of perfluorinated cycloderma tertiary amines (PFCT), as well as emulsions obtained their OS is ove
View of the investigational product (IP)The ratio of the cultivation environment / IPThe concentration of fluoride ionsThe rate of growth of the cells after cultivation
Wednesday cultivation-1,0100%
The mixture PFD and individual PFMSP20:11,090±15%
The mixture PFD and PFCT20:11,090±17%
The emulsion on the basis of individual PFMSP10:15,565±95%
Emulsion-based PPCT10:15,565±95%
* toxicity performancesin compounds were evaluated for growth inhibition of cultured transformed lymphoid cell line Raji.
Table 2

Comparison of the toxicity of various emulsions PFOS largest sub-lethal dose for mice and survival of rabbits
View of the investigational productAcute toxicity the La mice, LD50,ml per kgSurvival of rabbits (%) one year after intravenous study drug at a dose of 20 ml per kg of body weight
The emulsion on the basis of individual PFMSP140100,0
The emulsion on the basis of individual PFD1500,0
Emulsion-based PFD and individual PFMRP (2:1 ratio)140100,0
Emulsion-based PFD and PFCT (2:1 ratio)140100,0

Table 3

Comparison of the stability of the emulsion based on PDF/PFMRP and PFD/PFCT
View performancesin compounds included in the composition of the emulsionsThe increasing average size of particles in the original size of 0.08 μmThe optical density after mixing the emulsion with different concentrations of dextran in a ratio of 1:1
After 45 days of storage at 4°After 5 times of freezing and thawing Without dextran3% dextran6% dextran
PFD and PFMSP in the ratio 2:10,14±0,010,15±0,020,100,350,88
PFD and PFCT in the ratio 2:10,12±0,010,11±0,10,100,190,62

1. Perfluorinated cyclododecane tertiary amines of General formula (1)

where n=1; m=2 or 3,

X isor ,

as a basis getparentdir emulsions.

2. Perfluorinated cyclododecane tertiary amines of General formula (1) according to claim 1, selected from the group consisting of CIS/TRANS-isomers of performativity(Methylcyclopentane)Aminand; performativity-(4-methylcyclohexyl)amine; performativity-(4-methylcyclohexyl)amine and PERFLUORO-N-(4-methylcyclohexyl)-2-methylpyrrolidine.

3. A method of obtaining a perfluorinated cycloderma tertiary amines of General formula (1)

where n=1; m=2 or 3,

X isor

where n=1 Y=CF3and when n=2 Y=F,

electrochemical fluorination of p-piperidinemethanol is anhydrous hydrogen fluoride.

4. A mixture of perfluorinated cycloderma tertiary amines of General formula (1)

where n=1; m=2 or 3,

X isor

where n=1 Y=CF3and when n=2 Y=F,

as a basis getparentdir emulsions.



 

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