Aralen-bis(2-aminothiophene-3-carbonitrile)s as monomers for obtaining polyamides, polyazomethines and politician with phenylanaline groups

 

(57) Abstract:

The invention relates to the field of organic chemistry, specifically to new connections: dicyanodiamide, namely aralen-bis(2-aminothiophene-3-carbonitrile)am General formula

where R represents

Connection most effectively can be used as monomers for obtaining polyamides, polyazomethines and politician with phenylanaline groups with high values of viscosity and conductivity. table 1.

The invention relates to the field of organic chemistry, specifically to provide new compounds: dicyanodiamide, namely aralen-bis(2-aminothiophene-3-carbonitrile)s the General formula

,

where R represents

,

The claimed compounds can most effectively be used as monomers for obtaining polyamides, polyazomethines and politician with phenylanaline groups, which can find application in electronics.

These compounds, their properties are not described in literature.

Known 2,5-di-N-chlorothieno-3,4-dicyanamide:

(Wide, F.; Zellers, E. T. J. Am.Chem.Soc. 1980, 102 (12), 4283), p is the methylene.

Known 2-amino-4-phenyl-3-cyanothiophene:

(K. Gewald, H. Bottcher, E. Schinke Weg., 1966, Bd.99, s.94), obtained by the interaction of acetophenone with malonodinitrile and sulfur in ethanol presence of organic bases.

Known 2,5-diamino-3,4-dicyanamide (Nazarin O. E., Kazakov A. C., kukhtin C. A., Alekseev centuries, Clubs A. Y. Abramov, I. A., Grigoriev, R. S. Patent USSR No. 706414, C 07 D 333/26 priority December 30, 1979, application No. 2649394 on July 28, 1978)

which is produced by the bubbling of hydrogen sulfide into the solution tetracyanoethylene in dimethylformamide in the presence of pyridine at a temperature not exceeding +10 ° C, until a negative test for cyanide.

However, these compounds can serve as monomers for obtaining polyamides, polyazomethines and politician with phenylanaline groups.

The objective of the invention is to provide new compounds that can be used as monomers for obtaining polyamides, polyazomethines and politician with phenylanaline groups.

This object is achieved by the interaction of diacetylenes with malonodinitrile and powdered sulfur in ethanol in the presence of a catalyst, namely the research at a temperature of 30-40S.

These polymers are obtained by the following schema:

Polyamides.

;

These polyamides synthesized by the known method described in example 3: C. C. Vinogradov, V. Century Korshak, Y. S. Vygodskii, V. I. Zaitsev // polymer sciense ser. Conn., ser. And, No. 3, 1967, S. 653.

Polyazomethine

;

Data polyazomethine synthesized by the known method described in example 4: D. Wohrle, G. Kossmehl, G. Maneche // Makromolekulare Chemie, 1972, s.111.

Polyurea

;

These polyureas synthesized by the known method described in example 5: E. I., Hofbauer, M. F., Sorokin, V., Kolesnikov // polymer sciense ser. Conn., ser. In, No. 10, 1974, S. 758.

The following are specific examples of the preparation of the inventive monomers and polymers based on them.

The properties of the polymers listed in the table.

Example 1. Connection (a): 16.2 g of 1,4-diacetylbenzene, 6.6 g of malonodinitrile and 3.5 g of powdered sulfur is dissolved in 30 ml of ethanol, then added to the mixture with stirring, 10 ml of the research. Reactional to withstand the weight of 1-3 h at 30-40C. On cooling the product kr%, Tpl.=263-S, al. the analysis found (%)/calculated (%) (59,72/59,61); N(3,29/3,13); N(17,21/17,38), Expects, ; 3320(NHVal.), 2220(CN), 1530(C=Car.), 1280(NHDef.), mass spectrum(M/z)-322, range1H NMR, M. D.; 6,62(1H, s, thiophene), 7,20(2H, ush.S., NH2), a 7.62(2H, d, Ph).

Example 2. The compound (b): 23,8 g of 4,4’-diazetidine, 6.6 g of malonodinitrile and 3.5 g of powdered sulfur is dissolved in 30 ml of ethanol, then added to the mixture with stirring, 10 ml of the research. Reactional to withstand the weight of 1-3 h at 30-40C. On cooling the product crystallized. The isolated product is filtered and recrystallized from acetone.

Yield 81%, Tpl.=281-S, al. the analysis found (%)/calculated (%) (66,19/66,31); N(3,68/3,54); N(14,17/14,06), Expect. ; 3340(NHVal.), 2240(CN), 1560(C=Cap.), 1290(NHDef.), mass spectrum(M/z)-398, range1H NMR, M. D.; 6,60(1H, s, thiophene), 7,32(2H, ush.s, NH2), of 7.70(2H, d, Ph), 7,80(2H, d, Ph).

Example 3. Connection (C, d): to a solution of 0.005 mole of the corresponding diamine (a, b) 9.0 ml of dimethylacetamide (DMAC), cooled to-30C, type of 0.005 mol of acid chloride of terephthalic acid and stirred the reaction mixture at-30C for 30 minutes after reaching room temperature, the polymer solution was poured into water. The polymer is filtered off, p is 5, 1560, 1290. Compound (g): yield 93%; IR spectrum: cm-13320, 2220, 1700, 1560, 1280.

Example 4. Connection (e, f): a solution of 0.002 mole of terephthalaldehyde and 0.005 mol of the corresponding diamine (a, b) in 100 ml of N,N-dimethylformamide is heated at 150 for 5 hours Then add more of 0.003 mole of dialdehyde and warm for another 1 h at 150C. After cooling, the precipitated polymer is filtered off, washed with benzene and extracted with acetone.

The compound (d): yield 88%; IR spectrum: cm-13330, 2230, 1700, 1580.

Connection (e): yield 91%; IR spectrum: cm-13330, 2240, 1695, 1590.

Example 5. Connect (W, h): to a solution of 0.005 mole of the corresponding diamine (a, b) in 100 ml of N-methyl-2-pyrrolidone gradually add 0,005 mol of methylenedi-p-phenylene diisocyanate. The reaction is carried out at a stirring in a stream of dry nitrogen for 2 h at room temperature. Further, the polymer planted in acetone, filtered off, washed with benzene, ethyl ether and dried in vacuum at 80-90S.

The compound (W): yield 68%; IR spectrum: cm-13320, 2240, 1700, 1590.

The compound (C): yield 74%; IR spectrum: cm-13340, 2240, 1700, 1590.

The use of the inventive substances allows to obtain polyamides, polyazomethine and polyurea high is like orders of magnitude.

Aralen-bis(2-aminothiophene-3-carbonitrile)s the General formula

where

as monomers for obtaining polyamides, polyazomethines and politician with phenylanaline groups.

 

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< / BR>
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< / BR>
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FIELD: organic chemistry, pharmacy.

SUBSTANCE: invention relates to new derivatives of benzimidazole represented by the following formula (I) or its salt:

wherein R1 represents (lower)-alkyl group; R2 represents aromatic (lower)-alkyl group that can be substituted with one or more groups taken among halogen atom, alkyl group, halogen-(lower)-alkyl group, nitro-group, aromatic group, aromatic (lower)-alkoxy-group, (lower)-cycloalkyloxy-(lower)-alkyl group, aromatic (lower)-alkyl group, aromatic (lower)-alkenyl group, aromatic (lower)-alkynyl group, aromatic oxy-(lower)-alkyl group, (lower)-cycloalkyl-(lower)-alkoxy-group, alkenyl group, (lower)-alkoxy-group, (lower)-alkylthio-group and (lower)-alkanesulfonylcarbamoyl group; R3 represents alkyl group, hydroxy-(lower)-alkyl group, alkenyl group, aromatic group, halogenated aromatic group, (lower)-alkyl aromatic group, (lower)-alkenyl aromatic group or aromatic (lower)-alkenyl group; -X- represents cross-linking group represented by one of the following formulas: (II) , (III) , (IV) , (V) . Also, invention relates to pharmaceutical compositions eliciting activity that reduces blood glucose level based on this compound. Invention provides preparing new compounds and pharmaceutical compositions based on thereof used for prophylaxis and treatment of damaged tolerance to glucose, diabetes mellitus, insulin-resistance syndrome, vascular failures syndrome, hyperlipidemia and cardiovascular disorders.

EFFECT: valuable medicinal properties of compounds and compositions.

16 cl, 1 tbl, 86 ex

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SUBSTANCE: invention relates to new 1-(p-thienylbenzyl)-imidazoles of the formula (I): , wherein indicated residues represent the following values: R(1) means halogen atom, (C1-C4)-alkoxyl, (C1-C8)-alkoxyl wherein one carbon atom can be replaced with heteroatom oxygen atom (O); R(2) means CHO; R(3) means aryl; R(4) means hydrogen halogen atom; X means oxygen atom; Y means oxygen atom or -NH-; R(5) means (C1-C6)-alkyl; R(6) means (C1-C5)-alkyl in their any stereoisomeric forms and their mixtures taken in any ratios, and their physiologically acceptable salts. Compounds are strong agonists of angiotensin-(1-7) receptors and therefore they can be used as a drug for treatment and prophylaxis of arterial hypertension, heart hypertrophy, cardiac insufficiency, coronary diseases such as stenocardia, heart infarction, vascular restenosis after angioplasty, cardiomyopathy, endothelial dysfunction or endothelial injures, for example, as result of atherosclerosis processes, or in diabetes mellitus, and arterial and venous thrombosis also. Invention describes a pharmaceutical composition based on above said compounds and a method for their applying also.

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10 cl, 19 ex

FIELD: organic chemistry, medicine, endocrinology.

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EFFECT: valuable medicinal properties of compounds.

11 cl, 41 tbl, 243 ex

FIELD: organic chemistry, biochemistry.

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25 cl, 134 ex

FIELD: chemistry.

SUBSTANCE: invention claims compounds of the formula (I) with radicals as described in the claim, and medicine with inhibition effect on glycine absorption, based on compound of the formula (I) .

EFFECT: medicine for diseases treatment where glycine absorption inhibition can be effective.

21 cl, 1 tbl, 173 ex

FIELD: chemistry.

SUBSTANCE: invention relates to new compounds of formula , where R1 is -O-X, where X is -(CH2)m-(CR9R10)p-(CH2)n-Z-(CH2)q-W, where m, n and q are independently equal to zero or assume values from 1 to 5; p equals 0 or 1; R9 and R10 are independently hydrogen, hydroxy, halogen, lower alkyl, lower alkoxy or cycloalkyl; or R9 and R10 together represent alkylene, which together with the carbon atom to which the are bonded, form an aryl; Z is a bond or O, W is aryl; R2 is hydrogen; L is a bond; R3 is hydrogen; R4 is hydrogen; R5 and R6 are independently hydrogen; R7 is hydrogen, halogen, hydroxy, trifluromethyl, lower alkyl, lower alkoxy, alkanoyl, alkyloxyalkoxy, alkanoyloxy, amino, alkylamino, dialkylamino, acylamino, carbamoyl, carboxy, alkoxycarbonyl; or R5 and R6 together represent -(CH2)1-2-; Y is -(CH2)r-, -O-(CH2)r, -(CH2)r-O-, where r equals zero or assumes values from 1 to 3; Q together with atoms to which it is bonded form an aryl, pyridyl, pyrimidinyl, thienyl, furyl, pyrroliyl or indolyl ring; or to its pharmaceutically acceptable salts. The invention also relates to a method of inhibiting rennin activity in mammals, to a pharmaceutical composition, as well as to application.

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23 cl, 52 ex

FIELD: medicine, pharmaceutics.

SUBSTANCE: invention concerns a new glucitol derivative of formula (I): wherein m represents an integer chosen from 1-3; each R1, R2, R3 and R4 are independently choose from hydrogen atom and benzyl groups; Ar1 represents a naphthyl group which can be substituted by one or more substitutes chosen from the group, consisting of C1-C6alkyl group or halogen atom; A represents 5-7-members aromatic heterocyclic group containing one or more heteroatoms independently chosen from oxygen atom and sulphur atom which can form a condensed cycle with an aromatic carbocycle or an aromatic heterocycle where A can be substituted by one or more Rb provided when A is a benzocondensed cycle containing two or more rings, the group -(CH2)m- is connected with a heterocycle in A; Each Rb is independently chosen from C1-C6alkyl group, halogen atom and C1-C6-alkoxy group; or to their pharmaceutically acceptable salts. These compounds are used as a Na+ cotransport inhibitor and exhibits ability to reduce blood sugar level.

EFFECT: invention covers a pharmaceutical composition based on these compounds and to the method for treatment and prevention of such diseases associated with hyperglycemia, as diabetes, diabetes complications and obesity.

12 cl, 4 tbl, 5 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel 1-thio-D-glucitol compounds of formula I or to pharmaceutically acceptable salts thereof or hydrates of the compound or salts: , [where R1, R2, R3 and R4 are identical or different, and each is a hydrogen atom, C1-C6-alkyl group), A is -(CH2)n-, -CONH(CH2)n-, -O- or -(CH2)nCH=CH- (where n is an integer from 0 to 3, Ar1 is an arylene group, heteroarylene group, which is an unsaturated 5-9-member mono- or bicyclic group, containing 1-2 heteroatoms, selected from S and N, Ar2 is an aryl group or heteroaryl group which is an unsaturated 5-9-member mono- or bicyclic group containing 1-2 heteroatoms selected from O, S and N, and R5, R6, R7, R8, R9 and R10 are identical or different, and each is (i) a hydrogen atom, (ii) a halogen atom, (iii) a hydroxyl group, (iv) C1-8-alkyl group, optionally substituted with hydroxyl group(s), (v) -(CH2)m-Q {where m is an integer from 0 to 4, and Q is -CO2H, -ORc1, -CO2Ra3, -SRe1, -NHRa6 or -NRa7Ra7 (where each of Ra3, Ra6 and Ra7 is a C1-6-alkyl group, Rc1 is a C1-6-alkyl group, and Rc1 is a C1-6-alkyl group)}, (vi) -O-(CH2)m'-Q' {where m' is an integer from 1 to 4, and Q' is a hydroxyl group,-CO2H, -CO2Ra8, -CONRa10Ra10, -NRa12Ra12 (where each of Ra8, Ra10 and Ra12 is a C1-6-alkyl group)}, (vii) -ORf {where Rf is C3-7-cycloalkyl group or tetrahydropyranyl group)}, (viii) morpholine group, (ix) phenyl group, (x) pyridyl group]. The invention also relates to 1-thio-D-glucitol compounds of formulae IA, II, III, IV, to a pharmaceutical agent, to methods of obtaining 1-thio-D-glucitol compounds, as well as to compounds of formulae XIII, XIV.

EFFECT: obtaining novel biologically active compounds which are inhibitors of sodium-dependent co-transporter-2-glucose.

25 cl, 140 ex, 3 tbl

FIELD: chemistry.

SUBSTANCE: invention relates to synthesis of hydroperoxides of alkylaromatic hydrocarbons which can serve as a source of oxygen-containing organic compounds (phenol, methylphenols, acetone, cyclohexanone etc) and as an initiator of emulsion polymerisation of unsaturated hydrocarbons. The invention discloses a method for synthesis of hydroperoxides of alkylaromatic hydrocarbons through liquid-phase oxidation of these hydrocarbons with atmospheric oxygen at atmospheric pressure, process temperature of 110-130°C, for 1-3 hours in the presence of a 4-methyl-N-hydroxyphthalimide catalyst in amount of 1.0-2.0 wt %.

EFFECT: catalyst prevents use of an initiator and alkaline additives, which considerably simplifies the process, higher conversion of initial alkylaromatic hydrocarbons while preserving high selectivity of the process.

2 tbl, 2 ex

FIELD: chemistry.

SUBSTANCE: invention relates to novel compounds of formula (I) or pharmaceutically acceptable salts thereof, having CRP receptor antagonist activity. In formula (I) R1 denotes C3-C8 alkyl, optionally substituted with hydroxyl; phenyl optionally substituted with 1-3 substitutes selected from halogen, nitro, amino, hydroxyl, C1-C4 alkoxy, C1-C4 alkyl, optionally substituted with hydroxyl or C1-C4 alkylamino; naphthyl; C-bonded 5-6-member heteroaryl with 1-2 heteroatoms selected from S, N or O, optionally substituted with C1-C4 alkyl, C1-C4 alkoxy or acetyl; N-bonded 5-member heteroaryl with 1-2 heteroatoms selected from N, optionally substituted with 1-3 substitutes selected from C1-C4 alkyl or phenyl; R2 denotes phenyl, optionally substituted with 1-3 substitutes selected from C1-C4 alkyl, halogenC1-C4alkyl, C1-C4 alkoxy, halogenC1-C4alkoxy, halogen, hydroxy, di(C1-C4 alkyl)amino or di(C1-C4 alkyl)aminocarbonyl; or a heterocyclic group which is pyridyl, optionally substituted with 1-3 substitutes selected from C1-C4 alkyl, C1-C4 alkoxy or di(C1-C4 alkyl)amino; X denotes -NR3-, where R3 denotes C1-C4 alkyl, optionally substituted with hydroxyl, carboxyl or C1-C4 alkoxycarbonyl; Y1 denotes CR3a, where R3a denotes hydrogen, halogen, cyano, hydroxy, C1-C4 alkyl, optionally substituted with hydroxyl or halogen, C1-C4 alkoxy optionally substituted with halogen; Y2 denotes CR3b, where R3b denotes hydrogen or halogen; Y3 denotes N or CR3c, where R3c denotes hydrogen; and Z denotes O or -NR4-, where R4 denotes hydrogen.

EFFECT: invention also pertains to a method of producing compounds of formula (I), a pharmaceutical composition, an inhibiting method, CRF receptor antagonists and use thereof to prepare a medicinal agent.

25 cl, 9 tbl, 163 ex

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