Colorless water-soluble organic luminophores

FIELD: organic chemistry, luminophores.

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

 

The invention relates to organic phosphors, and more particularly to water-soluble organic phosphors that do not have color in daylight, and intermediates for them. Main area of use of the invention is invisible in daylight fluorescent ink paints and water-based ink used in manual protection office, accounting and other important business documents, as well as in microbiological research.

The majority of currently known water-soluble phosphors is painted, i.e. absorbing in the visible region of the spectrum phosphors, such as sulforhodamine, fluorescein sodium, eosine, acridine, curcumin, Riboflavin, erythrosine and some other (EP 1291396 A1). This limits the possibility of their use for manual protection.

Among the nearly colorless water-soluble phosphors as analogues of only a few water-soluble optical brighteners (Bmikeandvicki, Bambooteen "Organic phosphors", ed. "Chemistry" LO, 1976, p.222-240). However, these brighteners have only a blue fluorescence.

The technical problem on which this invention is directed, is to create a new water-soluble organic phosphors, not absorbing in the visible about the Asti spectrum and fluorescent different colors in the region from blue to yellow-orange.

A positive result of the task solution synthesis is achieved by known methods new, not previously described compounds - derivatives of a number of 2-phenylbenzoxazole containing acid groups providing solubility in water, and groups forming intramolecular hydrogen bond. The presence of the intramolecular hydrogen bonds leads to anomalously large Stokes shift, which is the cause of green, yellow or orange fluorescence of compounds that do not absorb in the visible region of the spectrum.

Example 1. 4-Amino-3-(benzo[d]thiazol-2-yl)benzosulfimide (I).

137,7 g of 2-aminothiophenol heated to 110° and add in small portions over 1 hour the amount of 203.9 g sotovogo anhydride, avoiding strong foaming. Then raise the temperature to 140° and continue heating at this temperature for 2-4 hours until complete disappearance of 2-aminothiophenol. The molten mass is poured into an enamel cuvette and after cooling the frozen mass, grind, and then boil for 2-3 hours with a solution of 12 g of NaOH in 3.5 l of water. The precipitate was separated by filtration and washed with cold water until disappearance of blue fluorescence in the wash water. The precipitate is dried at 80°. Get 200 g of 2-(benzo[d]thiazol-2-yl)phenylamine. The product is used without additional purification in the next stage.

100 g chopped 2-(benzo[d]thiazol-2-yl)phenylamine sprinkled with stirring in portions of 5-6 g for 2 hours to 500 ml of battery acid and stir until dissolved. The solution is filtered through a glass filter and poured into a mixture of 500 g of ice and 500 g of water. After reaction mass is cooled to room temperature, the precipitate is filtered off, washed with isopropyl alcohol and dried at 80°. Get 120 g sulfate salt of 2-(benzo[d]thiazol-2-yl)phenylamine. All the amount of sulphate is heated at 200° and a residual pressure of 10 mm Hg within 7-8 hours before the termination of the allocation of water. After cooling, the contents of the flask pour 4 liters of water, add NaOH to pH 9-10 and boiled with activated charcoal for 30 minutes. The hot solution is filtered. The filtrate is cooled to room temperature and acidified with hydrochloric acid to pH 1. The yellow precipitate was separated by filtration and washed with acetone. Get a connection I. Output : 100, Found: 51,0; N-3,3; N is 9.1. Calculated for C13H10N2O3S2WITH 50,97; N-3,29; N-9,14.

Example 2. Sodium salt of 4-(4,6-Dichloro-1,3,5-triazine-2-ylamino)-3-(benzo[d]thiazol-2-yl)benzosulfimide (II)

A suspension of 20.0 g of compound I in 400 ml of acetone is cooled to a temperature of 0-2°and at the same time from two drip funnels under stirring was added over 1 hour a solution of 18.5 g of aristovo cyanura in 150 ml of acetone and 100 ml of 10%aqueous solution of Na 2CO3. Stirring is continued until the disappearance of starting compound I (sample on TLC. Eluent: pyridine-isopropanol - conc. ammonia in volumetric ratio of 2:2:1). Upon completion of the reaction product is filtered off II and washed it on the filter with 100 ml of acetone. Dried at room temperature. The output 35, the Product is insoluble in water. Fluorescent green. Found: 40,4; N-1,7; N-14,7. Calculated for C16H8Cl2N5NaO3S2: C-40,35; H-1,69; N-14,7.

Example 3. Sodium salt of 4-(4-Chloro-6-[(3-sulfophenylazo)-1,3,5-triazine-ylamino])-3-(benzo[d]thiazol-2-yl)benzosulfimide (III)

35 g of compound II (example 2) add 400 ml of water, add the 15.6 g of sodium salt of meta-aminobenzenesulfonate and slowly heated to boiling. The precipitate dissolves. The reflux is continued for 3 hours, cooled to 60°, add 5 g of activated charcoal and boil for 30 minutes. The hot solution is filtered. After cooling the filtrate to room temperature, thereto was added 1 l of acetone. The precipitated phosphor is filtered off, washed on the filter with acetone and dried in air. The output 52, the Phosphor is highly soluble in water. Color fluorescence - green. Found: 41,5; N - 2,1; C1 - 5,6; N -13,2. Calculated for C22H13ClN6Na2O6S3With 41,61; N E 2.06; C1-To 5.58; N-13,23. The substance is highly soluble in water. Colorless aqueous solution has a yellow fluorescence is orescence with a maximum of 550 nm.

Example 4. Pentesilea salt of 4-(4,6-bis-diacetylene-1,3,5-triazine-2-ylamino)-3-(benzo[d]thiazol-2-yl)benzosulfimide (IV)

35,7 g of compound (II), 500 ml of water and a solution of 25 g iminodiacetic acid and 20 g of sodium carbonate in 150 ml of water is slowly heated to boiling and boiled for 3 hours. All the precipitate goes into solution. The mass is cooled to 60°add 5 g of activated charcoal, boiled for another 30 minutes and the hot solution filtered. The filtrate is acidified with hydrochloric acid to pH 1-2 and heated to complete dissolution of the precipitated sludge. Leave overnight at room temperature. The precipitation is filtered off, washed with water and dried in air. The output of the acid form of the compound IV is 38,

100 g of the acid form of the compounds IV pour 500 ml of water and gradually add to the mixture, potassium carbonate, ensuring complete dissolution of the precipitate. To the solution add 5 g of activated charcoal, boiled for 10 minutes and filtered. The cooled filtrate is poured onto 1.5 l of acetone under vigorous stirring. Dropped the precipitate was separated by filtration, washed with acetone and dried at room temperature. Exit 111, Found: 34,4; N-1,9; N-11,7; S-7,6. Calculated for C27H19N4To5O11S2WITH OF 34.40; N-1,92; N-11,70; S-7,65. The substance is highly soluble in water. Colorless aqueous solution has a yellow fluorescence with a maximum at 570 nm.

Example 5. Dinate the Wai salt of 4-(4-(2-(benzo[d]thiazol-2-yl)-4-sulfophenyl-amino)-6-chloro-1,3,5-triazine-2-ylamino)-3-(benzo[d]thiazol-2-yl)benzosulfimide (V)

a 3.83 g of compound I and 5 g of compound (II) pour 150 ml of water, adjusted the pH of the mixture of 10%aqueous solution of sodium carbonate to 8-10 and boil for 3 hours, maintaining the pH in the specified interval, adding, if necessary, a solution of Na2CO3. The formed white precipitate was separated by filtration, washed on the filter with water and dried at room temperature. The output of 6.1, the Substance has a yellow fluorescence. Difficultly soluble in water. Found: 45,4; N-2,0; N Is 12.8. Calculated for:C29H16ClN7Na2O6S4WITH-45,34; N-2,10; N-12,76.

Example 6. Disodium salt of 4-(4-(2-(benzo[d]thiazol-2-yl)-4-sulfophenyl-amino)-6-morpholino-1,3,5-triazine-2-ylamino)-3-(benzo[d]thiazol-2-yl)benzosulfimide (VI)

6 g of compound V, 0.73 g of the research and 150 ml of water is boiled for 3 hours, maintaining the pH of the mixture 8-10 using an aqueous solution of sodium carbonate (see example 5). 30 minutes after the start of boiling the precipitate goes into solution. Upon cooling the filtered solution was poured into acetone. Dropped the precipitate was separated by filtration, washed with acetone and dried at room temperature. The output of 3.5 was Found With 48,4; N-3,0; N-13,7; S-15,7. Calculated for C33H24N8Na2O7S4: C-48,40; N-2,95; N-13,68; S-15,66. The substance is highly soluble in water. Colorless aqueous solution is orange fluorescence with a maximum 582 nm.

Example 7. Disodium salt of 4-(2-carb is moviesoldschool)-3-(benzo[d]thiazol-2-yl)benzosulfimide (VII)

5 g of compound I and 80 ml of water is heated to dissolve the precipitate, cooled to 25° and sprinkled 1.85 g of sodium acetate. Thus, there is a partial precipitation. To the reaction mass immediately give 5,52 g of anhydride ortho sulfobenzoic acid and stirred at room temperature for 3 hours until complete disappearance of the thin chromatogram of compound I. Further, to the reaction mass is added activated charcoal, boiled for 15 minutes and filtered. The filtrate is evaporated on a water bath to dryness, the residue is washed with acetone, dissolved in minimum amount of water and planted with acetone. Get white powder with yellow fluorescence. The output of 3.7, Found: C-45, 0mm; N-2,2, N-5,3; S at 18.1. Calculated for C20H12N2Na2About7S3: C-44,94; H-OF 2.26; N-5,24; S-18,00. The substance is highly soluble in water. Colorless aqueous solution has a yellow-green fluorescence with a maximum 547 nm.

Example 8. Disodium salt of 4-(4-(carboxymethylamino)-6-chloro-1,3,5-triazine-2-iamino)-3-(benzo[d]thiazol-2-yl)benzosulfimide (VIII)

to 3.52 g of glycine and 2.5 g of sodium carbonate dissolved in 150 ml of water. To this solution was added 20 g of compound (II) and 300 ml of water. The suspension is slowly heated to 60° (the precipitate dissolves). The solution is carefully acidified with hydrochloric acid to pH 1-2. Dropped the precipitate was separated by filtration, washed with water and dried p. and room temperature. Get 4 g of compound VIII in the form of the free acid.

100 g of compound VIII in the form of the free acid is poured 500 ml of water and sprinkled of 40.9 g of sodium carbonate to dissolve the precipitate, add activated charcoal, boiled for 10 minutes, filtered. To the cooled filtrate is added 500 ml of acetone and the mixture is poured to 1 l of acetone. Dropped the precipitate was separated by filtration, washed with acetone and dried at room temperature. Exit 111, Found: 40,3; N-2,0; N-15,6. Calculated for C18H11ClN6Na2O5S2: C-40,27; H-2,07; N-15,65 Substance is highly soluble in water. Colorless aqueous solution has a yellow-green fluorescence with a maximum of 548 nm.

Example 9. Disodium salt of 4-(4-(3-sulfophenylazo)-6-morpholino-1,3,5-triazine-2-ylamino)-3-(benzo[d]thiazol-2-yl)benzosulfimide (IX)

2 g of Compound III, 0.3 g of the research and 60 ml of water is heated to boiling. Boil for 3 hours, maintaining the pH of 8-10. After cooling, the solution was poured into 1 l of acetone. Dropped the precipitate was separated by filtration, washed with acetone and dried at room temperature. The output of 0.38 was Found With 48,4; N-3,1; N-13,6; S-15,7. Calculated for C33H24N8Na2O7S4: C-48,40; N-2,95; N-13,68; S-15,66. The substance is highly soluble in water. Colorless aqueous solution has a yellow fluorescence with a maximum of 565 nm.

Example 10. Trinacria salt of 4-(4,6-bis-(carboxin is thylamino)-1,3,5-triazine-2-ylamino)-3-(benzo[d]thiazol-2-yl)benzosulfimide (X)

The synthesis are the same as compounds VIII, but take twice the amount of glycine. Output connections X 110, Found: 40,2; N-2,4; N is 16.5. Calculated for C20H14N7Na3O7S2: C-40,21; H-2,36; N-16,41. The substance is highly soluble in water. Colorless aqueous solution has a yellow fluorescence with a maximum of 565 nm.

Example 11. Sodium salt of 4-amino-3-(benzo[d]oxazol-2-yl)benzosulfimide

Thoroughly mixed mixture 109,13 g of 2-aminophenol and the amount of 203.9 g sotovogo anhydride is heated at 140° within 2-4 hours before the termination of the release of carbon dioxide. Then connect the vacuum (residual pressure of about 50 mm Hg) and continue heating at 180° for 3-4 hours before the termination of the allocation of water. The molten mass is poured into a porcelain mortar and then pour the crushed and then boiled for 2-3 hours with a solution of 12 g of sodium hydroxide in 3500 ml of water. After cooling, the resulting suspension is separated by filtration, washed with cold water until the disappearance of the blue fluorescence of wash water and dried at 80°. The yield of 2-(benzo[d]oxazol-2-yl)phenylamine 180-185, the Product is used without additional purification in the next stage.

To 500 ml of battery acid with stirring, in portions of 5-6 g for 2 hours sprinkled 100 g finely powdered 2-(benzo[d]oxazol-2-yl)phenylamine and stir to lead the dissolution of the precipitate. The solution is filtered through a glass filter and poured into a mixture of 500 g of ice and 500 g of water. After reaction mass is cooled to room temperature, separating the precipitate by filtration, washed it with isopropyl alcohol and dried at 80°. The output of the sulfate salt of 2-(benzo[d]oxazol-2-yl)phenylamine 110, All the resulting product is heated at 200° and a residual pressure of 50 mm Hg for 7-8 hours before the termination of the allocation of water. After cooling, the product is suspended in 4 l of water, add sodium hydroxide to a pH of 9-10, activated carbon and boil for 30 minutes. Then a hot solution is filtered. The filter cake is washed with 500 ml of hot water. The combined filtrates are cooled to room temperature, acidified with hydrochloric acid to pH 1. Fallen yellow precipitate was separated by filtration, washed with acetone and dried at room temperature. Output connections XI 90, Found: 53,8; N-3,5; N Is 9.6; S, 11,0. Calculated for C13H10N2O4S: C-53,79; H 3,47; N-9,65; S-11,05.

Example 12. Sodium salt of 4-(4,6-Dichloro-1,3,5-triazine-2-ylamino)-3-(benzo[d]oxazol-2-yl)benzosulfimide (XII)

Get exactly the same as compound II, but instead of compound I take a 19.6 g of compound XI. Output connections XII 32, was Found With 41,8; N-1,7; N-15,2. Calculated for C16H8Cl2N5NaO4S: C-41,76; H-1,75; N-15,22.

Example 13. Disodium salt of 4-(4-Chloro-6-[(3-sulfate is ylamino)-1,3,5-triazine-2-ylamino])-3-(benzo[d]oxazol-2-yl)benzosulfimide(XIII) 1 g of compound XII, 0,43 g metamelomai acid, 50 ml of water and 5 ml of 10%aqueous solution of sodium carbonate are heated at 40-45° within 4 hours until complete dissolution of the components. The hot solution is filtered. The filtrate is acidified with hydrochloric acid to pH 1. Dropped the precipitate was separated by filtration, washed with water and transferred into 25 ml of water. Bring sodium carbonate pH of the mixture to 8.0 to 8.5, filtered. The filtrate is diluted with 200 ml of isopropyl alcohol. The precipitation of compound XIII is separated by filtration and dried at 80°. Output 1 was Found With 42,7; N-2,1; N-13,6. Calculated for C22H13ClN6Na2O7S2: C-42,69; H-2,12; N-OF 13.58. The substance is soluble in water. Colorless aqueous solution has a green fluorescence with a maximum at 517 nm.

Example 14. TRAMONTINA salt of 4-(4-chloro-6-diacetylene-1,3,5-triazine-2-ylamino)-3-(benzo[d]oxazol-2-yl)benzosulfimide (XIV)

1.5 g of compound XII, 0,435 g iminodiacetic acid, 75 ml of water and 10 ml of 10%aqueous solution of sodium carbonate is heated 4 hours at 40-45° until complete dissolution of the components, filtered and the filtrate is acidified with hydrochloric acid to a pH of 1.0. Dropped the precipitate was separated by filtration, washed with water and transferred into 40 ml of water. Bring a 25% ammonia solution pH to 8.0 to 8.5. The solution is filtered. The filtrate is poured into 300 ml of isopropyl alcohol. The precipitation of compound XIV is separated by filtration is the Finance and dried at 80° . The output of 1.3 was Found: 41,0; H-4,1; N-21,4. Calculated for C20H24ClN9O8S: C-40,99; H-4,13; N-21,51. The substance is soluble in water. Colorless aqueous solution has a green fluorescence with a maximum at 517 nm.

Compounds of General formula

as a colorless water-soluble organic phosphors of different colors.



 

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14 ex

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29 cl, 36 dwg, 11 tbl, 6 ex

FIELD: chemistry.

SUBSTANCE: invention discloses a method of producing a compound of formula

through reaction of a compound of formula 2, where R1 denotes H, C1-C4 alkyl, cyclopropyl, cyclopropylmethyl or methylcyclopropyl, R2 denotes CH3 or Cl, and X denotes Cl or Br, with R1-NH2 in the presence of a carboxylic acid in an essentially anhydrous reaction medium containing a suitable organic solvent, as well as a method of producing a compound of formula

,

where R2 denotes CH3 or Cl, and X denotes O or Br, involving reaction of a compound of formula

,

where R3 denotes C1-C6 alkyl or C3-C6 alkenyl, each optionally substituted with not more than 3 halogen atoms and not more than 1 phenyl, with phosphorus tribromide. Also disclosed is a compound 4, where R2 denotes CH3 or Cl; R3 denotes C1-C6 alkyl or C3-C6 alkenyl, each optionally substituted with not more than 3 halogen atoms and not more than 1 phenyl; and X denotes Cl or Br; provided that when each of R2 and X denotes Cl, R3 is not CH3.

EFFECT: improved method of obtaining the compounds.

12 cl, 6 ex, 4 dwg, 4 tbl

FIELD: organic chemistry, luminophores.

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

FIELD: medicine; pharmacology.

SUBSTANCE: invention relates to the amyloid-binding compound or its water-soluble non-toxic salt, where Y is presented by NR1R2; Z means S; R1 is chosen from group consisting of H, methyl, propyl, (CH2)nOR' (where n = 1, 2 or 3 and R' is presented by H or by lowest alkyl group), CF3, CH2-CH2X, CH2-CH2-CH2X (where X = F, Cl, Br or I); where R2 is chosen from group consisting of lowest alkyl group, (CH2)nOR' (where n = 1, 2 or 3 and R' is presented by H or by lowest alkyl group), CF3, CH2-CH2X, CH2-CH2-CH2X (where X = F, Cl, Br or I); R3 - R10 are chosen independently from group, consisting of H, F, CI, Br, I, lowest alkyl group, (CH2)nOR' (where n = 1, 2 or 3) or OR' , and R' means H lowest alkyl group); provided, the compound isn't related one of the following compounds: methyl-[4-(6- methyl -benzothiazole-2-il)phenyl]amin, dimethyl -[4-(6- methyl - benzothiazole-2-il)phenyl]amin, and where at least one of R1-R10 substitutors contains the radioactive marker, chosen from group, which consists of 11C, 123I, 125I or 127I, and the described compounds don't contain the nitrogen quaternary atoms. The invented compounds are used for detection of the amyloid deposit in patient and in differential diagnostics of brain affected by Alzhemer's disease and normal brain. .

EFFECT: thioflavin derivatives are obtained for in vivo visualization and identification of amyloid deposit in patient.

16 cl, 2 tbl, 9 dwg, 9 ex

FIELD: chemistry.

SUBSTANCE: invention concerns oestrogen receptor modulators of the formula (II) with the structure where R1 is an alkenyl of 2-7 carbon atoms with alkenyl group optionally substituted by -CN or halogen; R2 and R2a are hydrogen or halogen independently of each other; R3 and R3a are hydrogen or halogen independently of each other; X is O; or their pharmaceutically acceptable salts. The invention also concerns a method of obtaining the claimed compounds, pharmaceutical composition, and treatment methods for various diseases.

EFFECT: obtaining of the claimed compounds.

39 cl, 23 tbl, 98 ex

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