The method of obtaining derivatives of aryl - or heteroarylboronic

 

(57) Abstract:

The inventive product - derived aryl - or heteroarylboronic f-crystals of 1 when the corresponding values radicals. Reagent 1: piperidine derivative f-crystals 2. Reagent 2: heterocycle f-crystals 3. Reaction conditions: in a medium of an organic solvent. The structure of the compounds f-l I - III are given in the text description. 3 C. p. F.-ly, 3 tables.

The invention relates to a method for producing derivatives of aryl(or heteroaryl)-piperazinil-butyl-azoles of the General formula (I):

Ar-NN-(CH2)4- (I) where AG nitrogen-containing aromatic radical, selected from a possibly substituted C1-C6by alkyl or halogen 2-pyrimidine, 2-N-methylimidazole and 3-(1,2-benzisothiazol); Z1a nitrogen atom or a carbon atom which may be substituted, denoted With R1;

Z2the nitrogen atom, or possibly substituted carbon atom marked With-R2;

Z4the nitrogen atom, or possibly substituted carbon atom marked With-R4;

R1,R2,R3and R4the same or different, a hydrogen atom, halogen, lower alkyl radical, a nitro radical, a hydroxyl radical, lower alkoxy radical, a cyano radical, carboxyla.

Derivatives of 1-(4-[4-[aryl(or heteroaryl)]-1-piperazinil]-butyl)-1H-azole General formula (I) are substances with pharmacological activity against Central nervous system, in particular they possess anxiolytic and trankvilizirujushchej activities, as well as antidepressant activity during inhibition of withdrawal symptoms and disorders associated with cognition, and affect the cardiovascular system, in particular exhibit antihypertensive activity [1]

Derivatives of 1-{4-[4-[aryl(or heteroaryl)]-1-piperazinil]-butyl}-1H-azo crystals obtained using the following methods.

The interaction of compounds of General formula (II):

Ar-NN-(CH2)4-X (II) where AG has the above meaning and X denotes a halogen atom or a group to delete, select tosyloxy or mesilate, with the compound of General formula (III):

H-, (III) where Z1,Z2,Z4and R3have the above values.

By reaction of compounds of General formula (IV):

X-(CH2)4-, (IV) where Z1,Z2,Z4, R3and X have the above meanings, with a compound of General formula (V):

Ar-NN-H (V) where AG is the above values.

By the reactions is sayasane values, with a compound of General formula (VII):

Ar X (VII) where Ar and X have the above values.

The interaction of compounds of General formula (VIII):

Ar-NN-(CH2)4-NH2(VIII) where Ar has the above meaning, with 2.5-dimethoxytetrahydrofuran.

The invention relates to a method for producing derivatives of General formula (I), which allows to improve the yield of these products.

According to the invention derivatives of General formula (I) are obtained by the coupling of compounds of General formula (IX):

Ar-NN X-, (IX) where AG and X have the above meanings, with a compound of General formula (III):

H-, (III) where Z1,Z2,Z4,R1,R2,R3and R4have the above values.

The reaction between the compounds of General formulas IX and III is carried out in an appropriate solvent, such as dimethyl sulfoxide; dimethylformamide; alcohol, such as ethanol or any propanolol or butanol; aromatic or non-aromatic hydrocarbon, such as heptane, benzene or toluene; a simple ether, such as dioxane or diphenyl ether; or a mixture of these solvents; preferably using dimethylformamide. This reaction is carried out in the presence of inorganic onok organic bases, such as pyridine, triethylamine or tert.-piperonyl potassium; preferably using potassium carbonate.

The most adequate temperature change from room temperature up to the boiling temperature under reflux of the solvent, preferably from 80 to 160aboutC, reaction time is 1-24 hours

Working thus have derived the General formula (I) with a very high degree of purity. These derivatives, in addition, get in the way, very simply implemented in the industry and gives a very high output.

The initial products of General formula IX is obtained by methods described, for example: J. Yevich, R. and J. other ed. Chem. 1986, 29, 359.

A large number of connections receive the proposed method. Their physico-chemical characteristics are shown in table.1-3. Getting several derivatives of General formula (I) described below in more detail.

P R I m e R 11. Obtain 4,5-dichloro-2-methyl-1-{4-(2-pyrimidinyl)-1-piperazin - Neil]-butyl}-1H-imidazole.

Within 14 hours at 130-135aboutWith a heated mixture of 450 g (1.5 mmol) of 8-(2-pyrimidinyl)-8-Aza-5-Sonisphere/4,5/-dainbramage, 225 g (1.5 mmol) of 4,5-dichloro-2-methylimidazole and 300 g (2.25 mmol) of potassium carbonate in 2 l of dimethylformamide. Evaporated poiut 503 g (91%) of 4,5-dichloro-2-methyl-1-{ 4-[4-(2-pyrimidinyl)-1-piperazinil] -butyl]-1H-imida - ash in liquid form.

Spectral data for the identification of this product are presented in table.1.

P R I m e R 16. Getting 1-{4-[4-(2-PI - rimidine)-1-piperazinil]-butyl]-1H-Ben - imidazole.

Heated at 140-145aboutC for 14 h in a mixture of 450 g (1.50 mmol) of 8-(2-pyrimidinyl)-8-Aza-5-Sonisphere/4,5/-dainbramage, 177 g (1.50 mmol) of benzimidazole and 307 g (2.25 mmol) of potassium carbonate in 2 l of dimethylformamide. Evaporated under vacuum, add chloroform, washed with water, dried over sodium sulfate, evaporated under vacuum and receive 457 g(91%) 1-{4-[4-(2-pyrimidinyl)-1-piperazinil] -butyl} 1H-benzimidazole melting temperature 85-88aboutC.

Spectral characteristics to identify this product are presented in table.1.

P R I m e R 27. Getting 1-4-4-(2-pyrimidinyl)-1-piperazinil-butyl-1H-Pirat - La.

Heated at 140aboutC for 14 h the mixture 730 g (3,59 mmol) 8-(pyrimidinyl)-8-Aza-5-Sonisphere (4,5)-decane-bromide, 275 g (of 4.05 mmol) of pyrazole and 745 g (5.4 mmol) of potassium carbonate in 3 liters of dimethylformamide. Evaporated under vacuum, add chloroform, washed with water, dried over sodium sulfate, evaporated under vacuum and get 650 g(94%) 1-{4-[4-(2-pyrimidinyl)-1-piperazinil]-butyl}-1H-PI - razole in liquid form.

Heated at 120-125aboutC for 22 h the mixture to 8.5 kg (28,41 mmol) of 8-(2-pyrimidinyl)-8-Aza-5-Sonisphere/4,5/-decembre-Mead, 3.5 kg (34,14 mmol) of 4-chloropyrazole and 5.5 kg (39.8 mmol) of potassium carbonate, 25.5 liters of dimethylformamide. Evaporated under vacuum, add chloroform, washed with water, dried over sodium sulfate, evaporated under vacuum and get 7,94 kg (87%) 4-chloro-1-{4-[4-(2-pyrimidinyl)-1-piperazinil] butyl}-1H-pyrazole in the form of liquid.

Spectral characteristics to identify this product are presented in table.1.

P R I m e R 77. Obtain 4,5-dichloro-2-methyl-1-{4-[4-(2-methoxyphenyl)-1-piperazinil]-butyl}-1H-imidazo La.

Heated at 130aboutC for 20 h in a mixture of 130 g (0.4 mmol) of 8-(2-methoxyphenyl)-8-Aza-5-Sonisphere/4,5/-Dean-bromide, 66 g (0.44 mmol) of 4,5-dichloro-2-methylimidazole and 8.2 g (0.6 mmol) of potassium carbonate in 700 ml of dimethylformamide. Evaporated under vacuum, add chloroform, washed with water, dried over sodium sulfate, evaporated under vacuum and get 130 g (82%) of 4,5-dichloro-2-methyl-1-{4-[4-(2-methoxyphenyl)-1-piperazinil]-butyl}-1H-imidazo La with a melting point 82-83aboutC.

Spectral characteristics to identify this product are presented in table.2.

P R I m e R 88. OL>C for 18 h in a mixture of 67 g (0,19 mmol) 8-(1,2-benzisothiazol-3-yl)-8-Aza-5-Sonisphere/4,5/-Dean - bromide, 20,5 g (0.2 mmol) 4-chloropyrazole and 41 g (0.3 mmol) of potassium carbonate, 300 ml of dimethylformamide. Evaporated under vacuum, add chloroform, washed with water, dried over sodium sulfate, evaporated under vacuum and get 60 g (80%) 4-chloro-1-{ 4-[4-(3-(1,2-benzisothiazolin))-1-piperazinil] -butyl}-1H-pyrazole in the form of liquid.

Spectral characteristics to identify this product are presented in table.3.

1. The METHOD of OBTAINING DERIVATIVES of ARYL - OR HETEROARYLBORONIC General formula

< / BR>
where Ar is phenyl which may be substituted with halogen, or WITH1- C4-alkoxy or nitrogen-containing heterocycle selected from the group: 2-N-Mei, 3-(1,2-benzisothiazol) or 2-pyrimidine, which may be substituted WITH1- C6-alkyl or halogen;

Z1is nitrogen or C-R1;

Z2is nitrogen or C-R2;

Z4is nitrogen or C-R4;

R1, R2, R3and R4- the same or different, hydrogen, halogen, lower alkyl, nitro, hydroxy, lower alkoxy, cyano, carboxyl, carboxamido, alkylcarboxylic, phenyl which may be substituted by lower alkoxyl proizvodnjo piperazine with a heterocyclic compound of General formula

< / BR>
where Z1, Z2, Z4and R3have the specified values,

in the environment of an organic solvent, characterized in that as a derivative of piperazine is used as a compound of General formula

< / BR>
where Ar has the specified value;

X is halogen.

2. The method according to p. 1, characterized in that the solvent used is dimethylformamide.

3. The method according to p. 2, characterized in that the reaction is carried out in the presence of potassium carbonate.

4. The method according to PP.1 to 3, characterized in that the reaction is carried out at 120 - 140oWith over 14 - 22 o'clock

 

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20 cl, 1 sch, 3 tbl, 31 ex

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12 cl, 1 dwg, 3 ex

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EFFECT: obtaining novel biologically active compounds possessing activity of enzyme FAAH inhibitors.

10 cl, 5 ex, 1 tbl

FIELD: medicine.

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EFFECT: agonistic activity to PPARδ and PPARα.

20 cl, 25 ex

FIELD: chemistry.

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EFFECT: obtaining compounds for pharmaceutical compositions, with agonistic activity towards PPARδ and/or PPARα.

28 cl, 155 ex

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15 cl, 17 tbl, 24 ex

FIELD: organic chemistry, medicine, ophthalmology, pharmacy.

SUBSTANCE: invention relates to new derivatives of nitrogen-containing heterocyclic compounds of the general formula (I): wherein X1, X2, X3, X4 and X5 mean -CH2 or one of them represents -NH and another X1-X5 represent -CH2; k = 0, 1 or 2; when t = 2, then radicals R1 are similar or different; R1 represents direct or branched (C1-C8)-alkyl or (C1-C8)-alkoxy-group; A means phenyl or pyridinyl; R2 means hydrogen atom (H), hydroxyl, halogen atom, (C1-C6)-alkyl, (C1-C6)-alkoxy-group; n = 0, 1-4; radicals R2 are similar or different, when n > 1; p = 0 or 1-5; Y means -OC(O); Z means -CH, or to their pharmaceutically acceptable salts. Compounds of the formula (I) possess agonistic activity with respect to muscarinic receptors and can be used in medicine as medicinal preparations for treatment of neurodegenerative diseases or diseases associated with increased intraocular pressure.

EFFECT: valuable medicinal properties of derivatives.

6 cl, 1 tbl, 2 dwg, 16 ex

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EFFECT: new compound; method of increased yield and selectivity.

1 tbl, 1 ex

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