Method for preparing pharmacopoeia bis-(1-vinylamidazole)-zinc diacetate

FIELD: organic chemistry, chemical technology.

SUBSTANCE: invention proposes an improved method for synthesis of bis-(1-vinylimidazole)-zinc diacetate representing a complex compound of zinc diacetate with 1-vinylimidazole and known as medicinal preparation acizol. Acizol is an effective antidote and antihypoxic agent of the broad spectrum of effect. Method for synthesis of 1-vinylimidazole metal with zinc diacetate of the composition 2:1 involves carrying reaction in the absence of solvent and using available commercial zinc diacetate of the formula Zn(OCOCH3)2 x 2 H2O in the stoichiometric mole ratio 1-vinylimidazole : salt in the range from 2.9:1 to 2:1, and synthesized pure product is isolated by water distilling off or its azeotropic mixture with 1-vinylimidazole. Method provides excluding the dehydration step of parent zinc salt from technological process and to decrease consumption of used reagent 1-vinylimidazole significantly, Invention provides significant reducing energetic and industrial consumptions, simplifying and decreasing cost of process and retaining the quantitative yield of highly pure pharmacopoeia acizol preparation.

EFFECT: improved method of synthesis.

4 ex

 

The invention relates to the field of organic chemistry, in particular to improvements in the method of producing metal complex of bis-(1-vinyl-imidazole)zincdiacetate.

Describes an improved method of obtaining complex compounds of zincdiacetate with 1-vinylimidazole - bis(1-vinylimidazole)zincdiacetate on the basis of which developed a new drug tsinkorganicheskih the drug, which is not only effective antidote (registration certificate R No. 001936/01-2002, 02.12.2002, RF Patents №№2070201, 2038079), but the antihypoxic drug with a wide spectrum of action (Patent of the Russian Federation№2115653, №2204392, №2247558, №2260427). The way to obtain a metal complex of 1-vinylimidazole with cindicates composition 2:1, characterized in that the reaction is carried out using the available trademark of crystalline zincdiacetate [Zn(ASON3)2·2H2O] in the solution a slight excess of reagent 1-vinylimidazole, or when the stoichiometric molar ratio of ligand: salt (interval from 2.9:1 to 2:1). The advantage of this method is that it allows you to exclude from the process stage of dehydration original zinc salts and significantly reduce the consumption of the used reagent is 1-vinylimidazole. The technical result is a substantial reduction in energy and operating costs, oprosti and cheaper process while maintaining the quantitative output of high-purity pharmaceutical drug.

Known for the synthesis of the complex bis(1-vinylimidazole)zincdiacetate with the release of 90% by the reaction of 1-vinylimidazole with the use of two-water zincdiacetate in acetone-ether mixture (1:3) (Patent RF №2070201).

There is also known a method of its production by the interaction of anhydrous zincdiacetate with 1-vinylimidazole in a mixture of acetone: ether (1:1), wherein the zinc complex is formed with the yield of 85%. For full selection of product from the mother liquor requires cooling the reaction mixture to 0-5° (RF Patent No. 2115653).

There is a patent of the RF No. 2118960, in which the process line for bis(1-vinylimidazole)zincdiacetate (output 89-93%) of dewatered zincdiacetate, reducing the cost allocation alzola from the mother solution is achieved by pre-dissolving 1-vinylimidazole in acetone-essential mix and install a special module for dewatering zincdiacetate.

Also known is a method of obtaining exit and 99.8% high purity of the complex bis(1-vinylimidazole)zincdiacetate (RF Patent No. 2254337), which is based on the use in the reaction in advance dehydrated salts zincdiacetate, the process goes in the absence of solvents and in substantial excess of 1-vinylimidazole (the molar ratio of azole: salt in the range from 10:1 to 3:1). Purification of the resulting complex (shaded excess of the original 1-Winnie the imidazole is used toluene - the organic solvent of the class II toxicity.

Each of these methods has significant drawbacks: the use in the process of obtaining metal complex fire and explosive solvents, a significant excess of reagent 1-vinylimidazole, the need for preliminary energy-intensive and prolonged dehydration trademark of crystalline zincdiacetate [Zn(ASON3)2·2H2O], the complexity of the selection of the drug with the solvent of the class II toxicity, which leads to high production costs, and not a high yield of finished product.

The present invention offers an improved simple method of getting the pharmacopoeial bis(1-vinylimidazole)zincdiacetate with quantitative yield (100%).

The technical task of the invention is to simplify and cheapen the method of producing complex bis(1-vinylimidazole)zincdiacetate by changing the process conditions, eliminating the preparatory stages and complex selection of the target product.

This solution is achieved by the fact that it is proposed to use in the process without prior dehydration is available trademark of crystalline zincdiacetate [Zn(ASON3)2·2H2O] and the process to be in slight excess of p the agent - 1-vinylimidazole in the interval ratio of initial compounds ligand: Zn(ASON3)2·2H2O from 2.9: 1 to 2.1:1, the stoichiometric ratio of the initial reagents (2:1), without using any organic solvent at a temperature of 20-25°and With stirring. Full selection of target ready complex bis(1-vinylimidazole)zincdiacetate is provided by the distillation of the formed water or azeotropic mixture of 1-vinylimidazole with water from the reaction mixture, followed by drying of the product.

This method allows to obtain bis(1-vinylimidazole)cindicates high degree of purity of 99.5-99.8 per cent). Physico-chemical parameters of selected samples of complex compounds correspond to the specifications of the Fund on the substance of pharmacopoeial preparation of bis(1-vinylimidazole)cindicates (No. 42-0409-2691-02).

The following examples illustrate the present invention.

Example 1. To 100,6 g (1.07 mol) of 1-vinylimidazole at 20-25°and With stirring, gradually add 81,2 g (of 0.37 mol) Zn(ASON3)2·2H2O (reagent ratio of 2.9:1). Upon completion of the reaction from the reaction flask is distilled at reduced pressure (10-20 mm Hg) azeotropic mixture of 1-vinylimidazole with water (about 44 g), dried, get 137,36 g (99,90%) complex bis(1-vinylimidazole)zincdiacetate with TPL 104-105°C. Found, %: 45,07; N To 4.68; N 14,87; Zn 17,52 .C 14H18N4O4Zn. Calculated, %: C 45,21; N 4,84; N 15,07; Zn 17,61. UV λmax224 nm.

Example 2. To 150,0 g (1.6 mol) of 1-vinylimidazole at 20-25°and With stirring, gradually add to 140.5 g (0,640 mol) Zn(ASON3)2·2H2(Reagent ratio of 2.5:1). Upon completion of the reaction from the reaction flask is distilled at reduced pressure (10-20 mm Hg) azeotropic mixture of 1-vinylimidazole with water (about 53 g), dried, get 237,7 g (99,95%) complex of bis-(1-vinylimidazole)zincdiacetate with TPL 103 -105°C. Found, %: C 45,15; N To 4.73; N 14,91; Zn 17,65. C14H18O4Zn. Calculated, %: C 45,21; N 4,84; N 15,07; Zn 17,61. UV λmax226 nm.

Example 3. To 165.0 g (1,76 mol) of 1-vinylimidazole at 20-25°and With stirring, gradually add covers 175.6 g (0.80 mol) of Zn(ASON3)2·2H2(Reagent ratio of 2.2:1). Upon completion of the reaction from the reaction flask is distilled at reduced pressure (10-20 mm Hg) azeotropic mixture of 1-vinylimidazole with water (about 43 g), dried, get 296,8 g (owner of 99.87%) complex bis(1-vinylimidazole)zincdiacetate with TPL 105-106°C. Found, %: C 45,13; N To 4.81; N 14,93; Zn 17,56. C14H18O4Zn. Calculated, %: C 45,21; N 4,84; N 15,07; Zn 17,61. UV λmax224 nm.

Example 4. To 108,0 g (1.15 mol) of 1-vinylimidazole at 20-25°and With stirring, gradually add 126,2 g (0,575 mol) Zn(ASON3)2·2H2About (the ratio reagent is 2:1). Upon completion of the reaction from the reaction flask is distilled at reduced pressure (10-20 mm Hg) water (about 20 g), dried, get 213,1 g (99,93%) complex bis(1-vinylimidazole)zincdiacetate with TPL 104-106°C. Found, %: C 45,21; N equal to 4.97; N 15,01; Zn 17,68. C14H18N4O4Zn. Calculated, %: C 45,21; N 4,84; N 15,07; Zn 17,61. UV λmax223 nm.

Infrared spectra of all the samples obtained bis(1-vinylimidazole)zincdiacetate identical position and intensities of the bands with absorption bands of the spectrum of the control sample.

Thus, it was established that the complex bis(1-vinylimidazole)cindicates can be obtained much easier compared to previously known methods. Implementation of the proposed method on an industrial scale will eliminate from process energy-consuming and time-consuming preliminary drying of water available commodity crystallohydrate of zincdiacetate Zn(ASON3)2·2H2O significantly reduce the consumption of the source reagent 1-vinylimidazole, and to eliminate fire, explosive and high-grade toxicity solvents (acetone, ether, toluene). This Pharmacopoeia purity of the complex bis(1-vinylimidazole)cindicates and it is almost quantitative yield is achieved with a considerable reduction of the process time and saving the political costs.

Literature

1. RF patent №2070201. Bis-(1-vinylimidazole)cindicates as an antidote carbon monoxide. Domnina Y.S., Skvortsova GG, Nikolaev, V.N., Urumov O.Y, V.V. Maslov // BI, 1996, No. 34.

2. RF patent №2038079. The antidote carbon monoxide. Domnina Y.S., Soshnikova A.I., M.G. Voronkov, Urumov O.Y, Tiunov L.A., Ryazanov SD, Chumakov CENTURIES, Harutyunyan, S., Sokolovskiy T.M., V.A. Serov, Iliev V.T. // BI, 1995, No. 18.

3. RF patent №2115653. Complex compounds of imidazoles, showing antidote and antihypoxant activity. Soshnikova A.I., Domnina Y.S., Tiunov L.A., Chumakov CENTURIES, V.A. Barinov, the Wart VK // BI, 1998, No. 20.

4. RF patent №2204392. For the treatment of psoriasis. Babadjanov HH, Babadjanova SH, Trofimov B.A., Stankevich VK, Bakalova L.V., Nechiporenko S. p., Grisak SHOSTAKOVICH, Shilov, V.N., Barinov VA // BI, 2003, No. 14.

1. The method of obtaining pharmacopoeial bis(1-vinylimidazole)-zincdiacetate interaction zincdiacetate with 1-vinylimidazole without solvent, followed by purification of the target product, characterized in that cindicates used in the form of two-water hydrated, and the process is carried out at a molar ratio of 1-vinylimidazole:two-water of hydrated zincdiacetate in the range from 2.9:1 to 2.0:1.

2. The method according to claim 1, characterized in that the cleaning is performed by a simple distillation of water or by distillation in the form azeotropic mixtures with 1-vinylamide the I.



 

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