Derivatives of 1,2-bis (5-phenyloxazole-2) benzene as an organic phosphor blue illumination

 

(57) Abstract:

Usage: as an organic phosphor blue glow. The inventive product is a derivative of 1,2-bis- (5-phenyloxazolyl-2)benzene f-ly I, where (a) R=H,CF C24H16N2O2exit 64% so pl. 110C. b) R - C6H5, BF C30H20N2O2so pl. 155C. c) R N(CH3)2, BF C26H21N3O2so pl. 118C. (d)R CH3, BF C25H18N2O2so pl. 126C. Reagent 1: 2-(5-phenyloxazolyl 2)benzoic acid. Reagent 2: SOCl2with subsequent treatment of the formed acid chloride of the corresponding-aminoacetophenone hydrochloride. Reaction conditions: 2 h at boiling, further processing of the acid chloride is carried out at 20C. 5 Il. table 2. F-La I:

The invention relates to new chemical compounds, particularly to derivatives of 1,2-bis-(5-phenyloxazolyl-2)Ben - ash formula I

R where R H (a); C6H5(b); N(CH3)2(c); CH3(d).

1,2-bis-(5-Phenyloxazolyl-2)benzene exhibits properties of organic phosphor blue illumination with abnormally large Stokes shift, which the luminescence spectrum is almost no overlap with the absorption spectrum. Therefore, the materials to their own radiation. The presence of these properties makes effective use of the compounds of formula I in scintillation systems with great length.

Among luminophores the closest the band of the light emission of the claimed compound is 1,3,5-triphenyl-2-pyrazoline (II) (maxabsorption 390 nmmaxluminescence 450 nm) [1]

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This compound is widely used as an optical bleach activator in the liquid and plastic scintillators. 1,2,3-Triphenyl-2-pyrazoline is one of the best activators for liquid scintillators. The scintillators based on it have a high scintillation efficiency and resistance to radiation. In addition, it is relatively affordable and cheap in production.

The disadvantage of 1,2,3-triphenyl-2-pyrazoline is its small stoxev shift (60 nm) and a significant overlap between the absorption spectra and emission, resulting in reduced transparency in the scintillators of great extent and limits its application.

The closest structure and the claimed chemical compounds is 1,4-bis-(5-phenyloxazolyl-2)benzene (III), known by the trade name (ERROR) produced industrial the active phosphor blue illumination (maxabsorption at 362 nmmaxluminescence 420 nm, stoxev shift 58 nm).

ERROR obtained by condensation of dichlorohydrin terephthalic acid-aminoacetophenone hydrochloride followed by cyclodehydration the compounds obtained in sulfuric acid [2]

ERROR has the same drawbacks as 1,3,5-triphenyl-2-pyrazoline, is a small (58 nm) stoxev shift and also a significant overlap of the spectra of luminescence and absorption, as well as the share of losing a fluorescent dye light is proportional to the number of acts of perevoploscenija, the spectra observed reabsorption affecting transparency painted them with polymeric materials to light their own radiation. For effective use of the phosphor in the polymer him spectra of luminescence and absorption should be spaced out enough to have a large stoxev shift) and the minimum overlapping integral. This is especially important when creating a scintillation polymer systems, where the transparency of the material to their own radiation of the dye plays a major role. The described connection is selected as a prototype as the most similar in structure and light.

The aim of the invention is the detection of what they Stokes shift and a smaller overlap of the absorption spectra and fluorescence.

This goal is achieved by a new chemical structure expressed by the formula I

R where R H (a); C6H5(b); N(CH3)2(c); CH3(d).

Unexpected for this structure is the fact that, for example in connection with (I)a position of the fringe fluorescence practically coincides with the position of the band fluorescence Arora, and the absorption band of the compound (I)in a comparison with Rororo significantly shifted in wavelength region, and it is even more wavelength than the absorption band of 2.5-diphenyloxazole (PPO). This is because in the unexcited state, the molecule of compound I is experiencing significant steric hindrance. As a result of mutual repulsion phenyloxazole fragments flat structure is disturbed, resulting in a loss of coupling between the fragments of the molecule. Upon excitation of the molecule is simplified and the pairing is restored. Thus absorb light single unpaired fragments, p-electronic system which differs significantly from the p-electron system Arora, this explains the big difference in their absorption spectra. At the same time in the excited state p-electronic system of simplified molecules join the ski coincide. Interesting is the fact that the introduction of substituents in the para-position of the terminal phenyl ring causes a General change in the position of absorption bands of luminescence and absorption of compounds I (a-d), but stoxev shift almost unchanged (about 160 nm).

Compounds I(a-d) is obtained by condensation of the acid chloride of 2-(5-phenyloxazolyl-2)benzoic acid with the appropriate-aminoacetophenone hydrochloride and subsequent cyclodehydration the compounds obtained in sulfuric acid. In turn, 2-(5-phenyloxazolyl-2)benzoic acid synthesized from penicillamine phthalic acid, obtained by the interaction of aminoacetophenone hydrochloride with phthalic anhydride, cyclodehydration in sulfuric acid.

P R I m e R 1. Obtain 1,2-bis-(5-phenyloxazolyl-2)benzene.

In a round bottom flask with a capacity of 400 ml equipped with a reflux condenser, boil and 26.9 g (0.1 mol) of 2-(5-phenyloxazolyl-2)benzoic acid in 300 ml of chloride tiomila for 2 hours and Then distilled off the excess chloride taanila (up to a capacity of 60-80 ml), add 100 ml of benzene is distilled off azeotrope of benzene and chloride tiomila. Adding benzene and distillation of the azeotrope repeat twice more. Then the flask was added 100 ml of benzene. Acostly 400 ml, equipped with a mechanical stirrer, dissolved in the minimum of water 17.1 g-aminoacetophenone hydrochloride. Then at room temperature under intensive stirring at once add the benzene solution of the acid chloride and poured in small portions saturated soda solution to pH 8. After this, the solution at the same temperature withstand 2 hours the precipitation is filtered off, washed with water and dried. Then in a round-bottom flask 500 ml dried product is dissolved with vigorous stirring and at room temperature in concentrated sulfuric acid. Stir the solution for 2 h at the same temperature. The resulting dark brown solution was poured on ice. The precipitation is filtered off, washed with water and dried. The output of 23.8 g (64%). Purify the obtained 1,2-bis-(5-phenyloxazolyl-2)benzene chromatographic column continuous action (sorbent kilogram, eluent hexane). So pl. 110aboutC.

Other connections get the same way.

The melting point and elemental analysis data are given in table. 1.

The structure of the obtained compounds are confirmed by the data of IR spectroscopy. On the spectrograms recorded in the solid phase (pill CVG), Pro-840, 1000-1030 and 1600-1620 cm-1) cycles.

Tests of derivatives of 1,2-bis-(5-phenyloxazolyl-2)benzene as an organic phosphor were measured absorption spectra and luminescence and defined stoxev shift the claimed chemical compounds and to compare the prototype (see Fig. 1 prototype, Fig. 2-5 compound I a-d).

Absorption spectra were measured on a spectrophotometer "Specord M-40"; luminescence spectra at the facility, consisting of a mirror monochromator SMR-3, receiver of optical radiation PMT-18, microammeter M-95. Photoluminescence was excited by a lamp SUDS-500, from the spectrum which quartz monochromator DFID-4 was isolated light with a wavelength of 313 nm. The magnitude of the Stokes shift was defined as the difference of the band maxima of the luminescence and absorption.

The overlapping integral was calculated as the area of overlap of the absorption spectra and luminescence. These tests are given in table. 2.

As can be seen from the table, the claimed chemical compounds have significant advantages over the prototype. So, stoxev shift it in the standard about 3 times higher than that of stockshow shift previously known compounds of similar structure (prototype). The integral of the overlap of its absorption spectra and the>These advantages of the claimed compounds allows to use them effectively in scintillation technique. Fabrication of large blocks on their basis will substantially increase light output and thereby increase their effectiveness. The use of these compounds will provide an opportunity to significantly improve the quality of luminescent materials.

Derivatives of 1,2-bis(5-phenyloxazole-2)benzene of the General formula

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where R is H, C6H5N(CH3)2CH3,

as the organic phosphor blue glow.

 

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SUBSTANCE: the present innovation deals with applying pharmaceutical composition as an antagonist of NPY Y5 receptor that contains the compound of formula I

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147 cl, 7 ex

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SUBSTANCE: invention relates to novel α-(N-sulfonamido)acetamides of the formula (I) or their optical isomers wherein values R1, R, R2 and R3 are given in the invention claim. Proposed compounds are inhibitors of production of β-amyloid peptide and can be used for inhibition of production of β-amyloid peptide. Also, invention relates to pharmaceutical composition based on these compounds and to a method for inhibition of production of β-amyloid peptide.

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22 cl, 23 sch, 4 tbl, 501 ex

FIELD: organic chemistry, biochemistry, pharmacy.

SUBSTANCE: invention relates to parecoxib sodium salt in crystalline form that possesses properties of selective inhibitor of cyclooxygenase-2 (COX-2) and can be used in treatment of, for example, inflammatory diseases and pain. Proposed crystalline forms show characteristic peaks of powder X-roentgenogram obtained with using Cu-source of radiation and expressed as angles 2θ and chosen from groups consisting of at least values 5.6; 9.6; 11.0 and 14.5 ± 0.2 angle (form A), and 4.2; 8.3; 12.4; 16.7; 17.5; 20.8 and 24.7 ± 0.2 angle (form B), and 8.8; 11.3; 15.6; 22.4; 23.5 and 26.4 ± 0.2 angle (form E) and wherein each form is anhydrous and non-solvated. Also, invention relates to a method for preparing crystalline form A and to a pharmaceutical composition.

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21 cl, 5 tbl, 12 dwg, 1 sch, 7 ex

FIELD: organic chemistry, biochemistry, enzymes.

SUBSTANCE: invention relates to compounds represented by the formula: wherein values of substitutes are given in the invention description. Also, invention relates to pharmaceutically acceptable salts of the compound that can be used in treatment and/or prophylaxis of cathepsin-dependent states or diseases of mammals. Proposed compound are useful in treatment of diseases wherein bone resorption inhibition is desired, such as osteoporosis, increased mineral density of bone and reducing risk of fractures. Proposed claimed compounds are designated for preparing a drug possessing the inhibitory activity with respect to cathepsin.

EFFECT: valuable medicinal and biochemical properties of compounds.

24 cl, 13 sch, 4 tbl, 15 ex

FIELD: chemistry.

SUBSTANCE: compound of formula I , its diastereomers or salts, where dot line represents optional double bond, m and p independently stand for 0, 1, 2 or 3; R1 stands for H, -N(R8)-C(O)-NR6R7, -N(R8)-S(O)2-NR6R7, -N(R8)-C(O)-N(R8a)-S(O)2-NR6R7, etc.; R1a stands for H or group OH; or R1 or R1a together form oxo; or R1 and R1a together with carbon atom, to which they are bound, form optionally substituted oxo spiro-condensed heterocyclic group, representing fully saturated 5-member monocyclic group, containing 2 nitrogen atoms; R2 stands for heteroaryl, (heteroary)alkyl, representing 5-6-member aromatic ring, contaning 1 nitrogen atom and/or 1 atom of oxygen and/or sulphur, and optionally condensed with aryl ring; aryl, (aryl)alkyl, alkyl, alkenyl or cycloalkyl, representing partly or fully saturated C3-C6 monocyclic structure, any of which can be optionally, independently, substituted with one or more groups T1, T2 or T3; J stands for bond, C1-4 alkylene, R3 stands for -R5, -C(Z1)-R5, -N(R8a1)-C(Z1)-R5, -N(R8a1)-C(Z1)-O-R5, -N(R8a1)-S(O)2-R5; R4 stands for alkyl, halogenalkyl, cycloalkyl, aryl, which can be optionally condensed with heteroaryl 6-member ring, containing 1-2 heteroatoms, selected from group SO2, N, etc.; R5 stands for -NR6aR7a or heteroaryl, (heteroaryl)alkyl, representing 5-6-member aromatic ring, which contains 1-3 nitrogen atoms and/or 1 or 2 atoms of oxygen or sulphur, optionally condensed with heteroaryl ring, representing 6-member aromatic ring, containing 1 nitrogen atom, etc.; R6a, R7a independently represent H, alkyl, aryl, (aryl)alkyl, heteroaryl, representing 5-6-member aromatic ring, which contains 1-2 nitrogen atoms, optionally condensed with aryl or heteroaryl ring, representing 6-member aromatic ring with 1 nitrogen atom; any of which can be optionally, independently, substituted with one or more groups T1c, T2c or T3c; R6, R7, R8, R8a, R8a1 R8a2, and R9, independently, represent H, alkyl, hydroxy, alkoxy, (hydroxy)alkyl, (alkoxy)alkyl, (cyano)alkyl, (alkenyl)alkyl, -NR12R13, cycloalkyl, (cycloalkyl)alkyl, optionally condensed with aryl; aryl, (aryl)alkyl, heteroaryl, (heteroaryl)alkyl, etc.; R10, R10a, R11 and R11a, independently, represent H, alkyl, aryl, (aryl)alkyl, , hydroxy, (hydroxy)alkyl; heteroaryl, (heteroaryl)alkyl, representing 5-member aromatic ring, which contains 2 nitrogen atoms, or R11 and R11a can together form oxogroup, or R10a can together with R11a form bond, or R10 can together with R9 form saturated 3-4-member cycle; R12 and R13, independently, represent H, alkyl; W represents =NR8a2, =N- CO2R8a2, =N- CN; X represents C(=O), C=N-CN; Z1represents =O, or =N-CN; RX represents one optional substituent, bound with any suitable carbon atom in cycle, independently selected from T1g, T2g or T3g. Compounds of formula I are applied for manufacturing medication for treatment of IKur-mediated disorders.

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13 cl, 694 ex, 1 tbl

Dpp-iv inhibitors // 2345067

FIELD: chemistry, pharmaceutics.

SUBSTANCE: claimed invention relates to novel compounds of general formula (I) Z-C(R1R2)-C(R3NH2)-C(R4R5)-X-N(R6R7) (I), or its pharmaceutically acceptable salt which is different because Z represents phenyl; where Z can be substituted with one or more R8, where R8 represents halogen; R1, R4 represent H; R2, R5 represent H; R3 represents H; X is selected from group consisting of S(O)2 and C(O); R6, R7 are independently selected from group consisting of H, (C(R29R30))m-X1-Z1 and (C(R31R32))n-X2-X3-Z2 and C1-4alkyl, which carries substitution with one or more R29a, where R29a is independently selected from group consisting of R29b and Z1, on condition that R6 and R7 are selected in such way that R6 and R7 were not simultaneously independently selected from group consisting of H, CH3, CH2CH3, CH2CH2CH3 and CH(CH3)2; R29 R29b, R30, R31, R32 are independently selected from group consisting of H, C1-6alkyl and N(R32a)-C1-6alkyl; R32a represents C1-6alkyl; m is 0, 1 or 2; n is 2; X1 is independently selected from group consisting of covalent bond, -C1-6alkyl and -C1-6alkyl-N(R33)-; X2 represents -N(R35)-; X3 represents -C(O)-; R33 represents C1-6alkyl; R35 represents H; Z1, Z2 are independently selected from group consisting of Z3 and -C(R37a)Z3aZ3b; R37a represents H; Z3, Z3a, Z3b are independently selected from group consisting of T1, T2, C1-6alkyl, C1-6alkyl-T1 and C1-6alkyl-T2; T1 represents phenyl; where T1 is optionally substituted with one or more R38; R38 being independently selected from group consisting of halogen, CN, R39, C(O)NH2, S(O)2NH2, OT3, C(O)N(R40)T3 and T3, T2 is selected from group consisting of C3-7cycloalkyl, indanyl, tetralinyl, heterocycle and heterobicycle, T2 optionally carries substitution with one or more R41, where R41 is independently selected from group consisting of halogen, R42, OH and T3; R39 is selected from group consisting of C1-6alkyl, O-C1-6alkyl, S-C1-6alkyl, C(O)N(R44)-C1-6alkyl, S(O)-C1-6alkyl and S(O)2-C1-6alkyl, where each C1-6alkyl optionally carries substitution with one or more R45, where R45 is independently selected from group consisting of F, N(R46R47) and T3; R42 represents C1-6alkyl, each C1-6alkyl optionally carries substitution with one or more R45, where R45 is independently selected from group consisting of F; R40, R46, R47 are independently selected from group consisting of H and C1-6alkyl; R44 represents H; T3 is selected from group consisting of T4 and T5; T4 represents phenyl, where T4 optionally carries substitution with one or more R51, where R51 is independently selected from group consisting of halogen, OR52, S(O)2N(R52R53), C1-6alkyl; R52, R53 are independently selected from group consisting of H and C1-6alkyl; T5 is selected from group consisting of heretocycle C3-7cycloalkyl, where T5 optionally carries substitution with one or more R54, where R54 represents C1-6alkyl; where heterocycle represents ring of cyclobutane, cyclopentane, cyclohexane, which can contain double bonds in number up to maximal, or aromatic or non-aromatic ring which is fully or partially saturated or unsaturated, and in which at least one carbon atom, maximally up to four carbon atoms, are substituted with heteroatom, selected from group including oxygen and nitrogen, and where ring is bound with remaining part of molecule through carbon or nitrogen atom; where heterobicycle represents heterocycle as stated above, which is condensed with phenyl or other heterocycle with formation of bicyclic ring system, on condition that the following compound is excluded from claim:3-amino-N-cyclohexyl-4-phenylbutyramide. Invention also relates to pharmaceutical composition based on compound of general formula (I) and to their application for manufacturing medication for treatment and/or prevention of conditions during which it is desirable to inhibit DPP-IV.

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26 cl, 8 tbl, 193 ex

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2 cl, 3 ex

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4 cl, 6 ex

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1 tbl

FIELD: polymer materials.

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13 cl, 3 ex

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SUBSTANCE: invention relates to colorless at daylight organic luminophores, in particular, to novel, water-soluble, colorless luminophores A of the formula:

wherein X means oxygen (O) or sulfur (S) atom; Q means compounds of the formulas and wherein R1 and R2 taken separately or in common mean compounds of the formulas: -NHCH2COOM, -N(CH2COOM)2, Cl wherein M means Na, K, NH4. As comparing with the known colorless organic luminophores - optical whitening agents possessing with blue-sky blue fluorescence only, novel luminophores show fluorescence in the range from blue to yellow-orange color and can be used as components of fluorescent, colorless at daylight, inks for jet printers or stamp dyes.

EFFECT: improved and valuable properties of luminophores.

14 ex

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SUBSTANCE: invention relates to novel compounds, namely zinc bis-[2-(tosylamino)benzylidene-N-alkyl(aryl, hetaryl)aminates] of the general formula (I): wherein Ts means tosyl; R means (C1-C6)-alkyl with exception isopropyl, (C1-C6)-alkyl-substituted phenyl, (C1-C6)-alkoxy-substituted phenyl with exception para- and ortho-methoxyphenyl, pyridyl, (C1-C6)-alkylpyridyl, or R + R form in common disulfidodialkyl group -(CH2)n-S-S-(CH2)n- wherein n = 1-3, but preferably to zinc bis-[2-(tosylamino)benzylidene-N-alkylidenemercaptoaminates] of the general formula (Ia): Compounds can be used for synthesis of light-radiating organic diode of white and visible light. Fluorescence can be observed in blue region of spectrum with fluorescence bands maximum at 428-496 nm. Quantum yields are 0.2-0.25.

EFFECT: valuable physical properties of compounds.

5 cl, 8 ex

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