RU2353613C1 - Highly labelled by tritium [methyl-3h]methyltosylate - Google Patents
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- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 title claims abstract description 23
- 229910052722 tritium Inorganic materials 0.000 title claims abstract description 16
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 title claims abstract description 15
- 230000015572 biosynthetic process Effects 0.000 abstract description 7
- 238000003786 synthesis reaction Methods 0.000 abstract description 7
- 150000001875 compounds Chemical class 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract 1
- 150000003649 tritium Chemical class 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000004128 high performance liquid chromatography Methods 0.000 description 11
- 230000014759 maintenance of location Effects 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- RDOXTESZEPMUJZ-UHFFFAOYSA-N anisole Chemical compound COC1=CC=CC=C1 RDOXTESZEPMUJZ-UHFFFAOYSA-N 0.000 description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000003708 ampul Substances 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- FFEARJCKVFRZRR-BYPYZUCNSA-N L-methionine Chemical compound CSCC[C@H](N)C(O)=O FFEARJCKVFRZRR-BYPYZUCNSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000009826 distribution Methods 0.000 description 4
- 229930182817 methionine Natural products 0.000 description 4
- 239000008363 phosphate buffer Substances 0.000 description 4
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 description 3
- PVFOHMXILQEIHX-UHFFFAOYSA-N 8-[(6-bromo-1,3-benzodioxol-5-yl)sulfanyl]-9-[2-(2-bromophenyl)ethyl]purin-6-amine Chemical compound C=1C=2OCOC=2C=C(Br)C=1SC1=NC=2C(N)=NC=NC=2N1CCC1=CC=CC=C1Br PVFOHMXILQEIHX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N methoxybenzene Substances CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 3
- GATUGNVDXMYTJX-UHFFFAOYSA-N methyl 4-phenylbenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=CC=C1 GATUGNVDXMYTJX-UHFFFAOYSA-N 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- XLOXYWLRAKCDQL-UHFFFAOYSA-N 1-methyl-4-[(4-methylphenyl)sulfonylmethylsulfonyl]benzene Chemical compound C1=CC(C)=CC=C1S(=O)(=O)CS(=O)(=O)C1=CC=C(C)C=C1 XLOXYWLRAKCDQL-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical class [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FFFHZYDWPBMWHY-VKHMYHEASA-N L-homocysteine Chemical compound OC(=O)[C@@H](N)CCS FFFHZYDWPBMWHY-VKHMYHEASA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 2
- 230000011987 methylation Effects 0.000 description 2
- 238000007069 methylation reaction Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JKFYKCYQEWQPTM-UHFFFAOYSA-N 2-azaniumyl-2-(4-fluorophenyl)acetate Chemical compound OC(=O)C(N)C1=CC=C(F)C=C1 JKFYKCYQEWQPTM-UHFFFAOYSA-N 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 229910021612 Silver iodide Inorganic materials 0.000 description 1
- AOZUYISQWWJMJC-UHFFFAOYSA-N acetic acid;methanol;hydrate Chemical compound O.OC.CC(O)=O AOZUYISQWWJMJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000148 ammonium phosphate Inorganic materials 0.000 description 1
- 235000019289 ammonium phosphates Nutrition 0.000 description 1
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical class BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
- NZZFYRREKKOMAT-UHFFFAOYSA-N diiodomethane Chemical compound ICI NZZFYRREKKOMAT-UHFFFAOYSA-N 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- IYJMSDVSVHDVGT-PEQKVOOWSA-N metildigoxin Chemical compound O1[C@H](C)[C@@H](OC)[C@@H](O)C[C@@H]1O[C@@H]1[C@@H](C)O[C@@H](O[C@@H]2[C@H](O[C@@H](O[C@@H]3C[C@@H]4[C@]([C@@H]5[C@H]([C@]6(CC[C@@H]([C@@]6(C)[C@H](O)C5)C=5COC(=O)C=5)O)CC4)(C)CC3)C[C@@H]2O)C)C[C@@H]1O IYJMSDVSVHDVGT-PEQKVOOWSA-N 0.000 description 1
- 229960003746 metildigoxin Drugs 0.000 description 1
- ZGJADVGJIVEEGF-UHFFFAOYSA-M potassium;phenoxide Chemical compound [K+].[O-]C1=CC=CC=C1 ZGJADVGJIVEEGF-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229940045105 silver iodide Drugs 0.000 description 1
- JUDUFOKGIZUSFP-UHFFFAOYSA-M silver;4-methylbenzenesulfonate Chemical compound [Ag+].CC1=CC=C(S([O-])(=O)=O)C=C1 JUDUFOKGIZUSFP-UHFFFAOYSA-M 0.000 description 1
- BHAQUPQVBXPZQC-UHFFFAOYSA-M sodium;4-phenylbenzoate Chemical compound [Na+].C1=CC(C(=O)[O-])=CC=C1C1=CC=CC=C1 BHAQUPQVBXPZQC-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
Abstract
Description
Изобретение относится к органической и аналитической химии и может найти применение в синтезе медицинских и биологических препаратов.The invention relates to organic and analytical chemistry and may find application in the synthesis of medical and biological preparations.
Известно, что замена атомов водорода в органическом соединении на атомы трития не приводит к изменению каких-либо свойств исходного соединения (Evans Е.А. - Tritium and its compounds London Butterworths, 1974, p.48) [1].It is known that the replacement of hydrogen atoms in an organic compound with tritium atoms does not lead to a change in any properties of the starting compound (Evans EA - Tritium and its compounds London Butterworths, 1974, p. 48) [1].
Известен метилтозилат - соединение формулы:Known methyltosylate is a compound of the formula:
Он является донором метальной группы и используется для метилирования органических соединений. B.Pelan, M.Milohnoja, M.Pezdirc U.S. Patent 4145528 03.20, 1979 Process for preparing β-methyldigoxin [2].It is a methyl group donor and is used for methylation of organic compounds. B. Pelan, M. Milohnoja, M. Pezdirc U.S. Patent 4145528 03.20, 1979 Process for preparing β-methyldigoxin [2].
Однако высокомеченный тритием ([метил-3H]-H]метилтозилат) не описан.However, highly labeled tritium ([methyl- 3 H] -H] methyltosylate) is not described.
Техническим результатом, достигаемым настоящим изобретением, является расширение ассортимента меченых реагентов.The technical result achieved by the present invention is to expand the range of labeled reagents.
Достигается указанный технический результат получением высокомеченного тритием метилтозилата формулы I:This technical result is achieved by obtaining highly labeled with tritium methyltosylate of the formula I:
На фиг.1 показано: Распределение радиоактивности при анализе методом ВЭЖХ реакционной смеси, образовавшейся при каталитическом дегалоидировании бром-производного по метоксигруппе метилтозилата в атмосфере газообразного трития.Figure 1 shows: The distribution of radioactivity in the analysis by HPLC of the reaction mixture formed during the catalytic dehalogenation of a bromine derivative at the methoxy group of methyltosylate in an atmosphere of gaseous tritium.
На фиг.2 показано: Распределение оптической плотности (а) и радиоактивности (б) при анализе методом ВЭЖХ смеси, образовавшейся при реакции между [метил-3Н]метилтозилатом и натриевой соли п-фенилбензойной кислоты.Figure 2 shows: The distribution of optical density (a) and radioactivity (b) by HPLC analysis of the mixture formed during the reaction between [methyl- 3 H] methyltosylate and the sodium salt of p-phenylbenzoic acid.
На фиг.3 показано: Распределение оптической плотности и радиоактивности при анализе методом ВЭЖХ смеси, образовавшейся при реакции между [метил-3H]метилтозилатом и фенолятом калия.Figure 3 shows: The distribution of optical density and radioactivity in the analysis by HPLC of the mixture formed during the reaction between [methyl- 3 H] methyltosylate and potassium phenolate.
На фиг.4 показано: (а) - Хроматографическая подвижность метионина при анализе его методом ВЭЖХ; (б) - распределение радиоактивности [метил-3H]метионина при анализе его методом ВЭЖХ.Figure 4 shows: (a) - Chromatographic mobility of methionine when analyzing it by HPLC; (b) the distribution of the radioactivity of [methyl- 3 H] methionine when analyzed by HPLC.
Ниже приведены примеры реализации изобретения.The following are examples of the implementation of the invention.
Пример 1. Синтез бром-производного по метоксигруппе метилтозилатаExample 1. Synthesis of a bromo derivative at the methoxy group of methyltosylate
Смесь 1.48 г тозилата серебра и 0.78 г дииодметана в 5 мл сухом ацетонитрила кипятили 3 ч. Выпал осадок йодистого серебра, который отбросили, раствор упарили, после перекристаллизации полученного осадка из абсолютного этанола получено 1.13 г дитозилметана (выход - 60%).A mixture of 1.48 g of silver tosylate and 0.78 g of diiodomethane in 5 ml of dry acetonitrile was boiled for 3 hours. A precipitate of silver iodide was discarded, the solution was evaporated, and after recrystallization of the obtained residue from absolute ethanol, 1.13 g of ditosylmethane was obtained (yield - 60%).
Раствор 0.5 г дитозилметана в 3 мл ацетона смешивали с раствором 0.23 г бромистого лития в 2 мл ацетона, выдерживали при перемешивании при 60°С 5 мин и оставляли на ночь при комнатной температуре. Затем к реакционной смеси добавляли равный объем хлористого метилена и осадок центрифугировали. Выход бром-производного по метоксигруппе метилтозилата - 50%. После очистки бром-производного по метоксигруппе метилтозилата методом ВЭЖХ на колонке Kromasil C18 7 мкм, 4.6×150 мм, система: 60% метанол в фосфатном буфере (рН 2.8), скорость потока 1 мл/мин, время удерживания - 5.46 мин, выход бром-производного по метоксигруппе метилтозилата - 42%.A solution of 0.5 g of ditosylmethane in 3 ml of acetone was mixed with a solution of 0.23 g of lithium bromide in 2 ml of acetone, kept under stirring at 60 ° С for 5 min and left overnight at room temperature. Then, an equal volume of methylene chloride was added to the reaction mixture, and the precipitate was centrifuged. The yield of bromine derivative at the methoxy group of methyltosylate is 50%. After purification of the bromo derivative by the methoxy group of methyltosylate by HPLC on a
Пример 2. Синтез высокомеченного тритием [метил-3H]метилтозилатаExample 2. Synthesis of highly labeled tritium [methyl- 3 H] methyltosylate
Раствор 1.5 мг бром-производного по метоксигруппе метилтозилата в 0.2 мл бензола вносили в ампулу с 30 мг 5% Pd/СаСО3. Затем ампулу замораживали жидким азотом, вакуумировали до давления 0.1 Па и заполняли газообразным тритием до давления 333 гПа. Реакцию вели при комнатной температуре в течение 4 ч при перемешивании. Затем ампулу вновь замораживали жидким азотом и вакуумировали. Катализатор отфильтровывали и промывали 0.3 мл метанола. [метил-3H]Метилтозилат очищали методом ВЭЖХ на колонке Kromasil C18 7 мкм, 4.6×150 мм, система 60% метанол-вода-уксусная кислота (600:399:1), скорость потока 0.8 мл/мин, время удерживания - 3.86 мин. Анализ реакционной смеси (фиг.1) проводили методом ВЭЖХ на колонке Kromasil C18 7 мкм, 4.6×150 мм, система 60% метанол в фосфатном буфере (рН 2.8), скорость потока 1 мл/мин, время удерживания - 2.72 мин. Элюат разбавляли 10 мл воды и [метил-3H]метилтозилат экстрагировали свежеперегнанным эфиром (3×2 мл). Эфир упаривали и [метил-3H]метилтозилат растворяли в растворителе, в котором планировалось проведение метилирования. Выход высокомеченного тритием [метил-3H]метилтозилата - 50-60%, молярная радиоактивность - 15-17 Ки/ммоль.A solution of 1.5 mg of the bromo derivative at the methoxy group of methyltosylate in 0.2 ml of benzene was added to a vial of 30 mg of 5% Pd / CaCO 3 . Then, the ampoule was frozen with liquid nitrogen, evacuated to a pressure of 0.1 Pa and filled with gaseous tritium to a pressure of 333 hPa. The reaction was carried out at room temperature for 4 hours with stirring. Then the ampoule was again frozen with liquid nitrogen and evacuated. The catalyst was filtered off and washed with 0.3 ml of methanol. [methyl- 3 H] Methylosylate was purified by HPLC on a
Ниже приведены примеры, иллюстрирующие применение высокомеченного тритием [метил-3H]метилтозилата.The following are examples illustrating the use of tritium-labeled [methyl- 3 H] methyltosylate.
Пример 3. Синтез [метил-3H]метил-п-фенилбензоатаExample 3. Synthesis of [methyl- 3 H] methyl-p-phenylbenzoate
Натриевую соль п-фенилбензойной кислоты получали обработкой раствора 2 мг кислоты в 0.3 мл метанола 10 мкл 1 М NaOH. Раствор упаривали и лиофилизировали.Sodium salt of p-phenylbenzoic acid was obtained by treating a solution of 2 mg of acid in 0.3 ml of methanol, 10 μl of 1 M NaOH. The solution was evaporated and lyophilized.
В реакционную ампулу помещали раствор высокомеченного тритием [метил-3H]метилтозилата в 0.2 мл DMFA и 1.5 мг натриевой соли п-фенилбензойной кислоты. Ампулу запаивали, грели в течение 10 мин при 70°С при перемешивании и оставляли на 15 ч при 20°С. Практически вся метка содержалась в образовавшемся [метил-3H]метил-п-фенилбензоате. Анализ реакционной смеси (фиг.2) проводили методом ВЭЖХ на колонке Kromasil C18 7 мкм, 4.6×150 мм, система 60% метанол в фосфатном буфере (рН 2.8), скорость потока 1 мл/мин, время удерживания [метил-3H]метил-п-фенилбензоата - 18.19 мин (время удерживания п-фенилбензойной кислоты - 11.14 мин).A solution of highly tritiated [methyl- 3 H] methyltosylate in 0.2 ml of DMFA and 1.5 mg of p-phenylbenzoic acid sodium salt was placed in the reaction vial. The ampoule was sealed, heated for 10 min at 70 ° C with stirring, and left for 15 hours at 20 ° C. Almost the entire label was contained in the resulting [methyl- 3 H] methyl-p-phenylbenzoate. Analysis of the reaction mixture (FIG. 2) was carried out by HPLC on a
Пример 4. Синтез [метил-3H]анизолаExample 4. Synthesis of [methyl- 3 H] anisole
Раствор фенола (30 мг) в 1.2 мл DMSO перемешивали с 40 мг К2СО3 в течение 30 мин. К аликвоте этой смеси (120 мкл) прибавляли 0.3 мг высокомеченного тритием [метил-3Н]метилтозилата и грели 10 мин при 70°С. Анализ реакционной смеси (фиг.3) проводили методом ВЭЖХ на колонке Kromasil C18 7 мкм, 4.6×150 мм, система: 60% метанол в фосфатном буфере (рН 2.8), скорость потока 1 мл/мин, время удерживания анизола - 4.67 мин (время удерживания фенола - 1.93 мин). Практически вся метка содержалась в образовавшемся [метил-3H]анизоле.A solution of phenol (30 mg) in 1.2 ml of DMSO was mixed with 40 mg of K 2 CO 3 for 30 minutes. An aliquot of this mixture (120 μl) was added with 0.3 mg of highly labeled tritium [methyl- 3 N] methyltosylate and heated for 10 min at 70 ° C. Analysis of the reaction mixture (Fig. 3) was carried out by HPLC on a Kromasil
Пример 5. Синтез (метил-3H]метионинаExample 5. Synthesis of (methyl- 3 H] methionine
В ампулу вносили раствор 0.5 мг гомоцистеина в смеси 125 мкл тетрагидрофурана и 50 мкл воды, затем добавляли 7 мкл 1 М NaOH и 0.25 мг высокомеченного тритием [метил-3H]метилтозилата. Ампулу запаивали, грели при 70°С 10 мин, затем нагревание прекращали и через 60 мин растворители удаляли лиофилизацией. Анализ реакционной смеси (фиг.4) проводили методом ВЭЖХ на колонке Supelcosil ABZ+Plus 5 мкм, 4.6×250 мм, система: 50 mM аммоний фосфатный буфер, рН 2.8, скорость потока 1 мл/мин, время удерживания метионина - 4.10 мин (время удерживания гомоцистеина - 3.30 мин).A solution of 0.5 mg of homocysteine in a mixture of 125 μl of tetrahydrofuran and 50 μl of water was added to the ampoule, then 7 μl of 1 M NaOH and 0.25 mg of tritiated [methyl- 3 H] methyltosylate were added. The ampoule was sealed, heated at 70 ° C for 10 min, then the heating was stopped and after 60 min the solvents were removed by lyophilization. Analysis of the reaction mixture (Fig. 4) was carried out by HPLC on a Supelcosil ABZ + Plus 5 μm, 4.6 × 250 mm column, system: 50 mM ammonium phosphate buffer, pH 2.8,
Таким образом, получено новое высокомеченное тритием соединение - высокомеченный тритием [метил-3H]метилтозилат, при использовании которого можно синтезировать меченные тритием соединения.Thus, a new tritium-labeled compound was obtained — tritium-labeled [methyl- 3 H] methyltosylate, which can be used to synthesize tritium-labeled compounds.
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2089532C1 (en) * | 1995-03-31 | 1997-09-10 | Институт молекулярной генетики РАН | Method of preparing quaternary amine salts containing tritium labelled aromatic radical at nitrogen atom |
| RU2291142C1 (en) * | 2005-11-17 | 2007-01-10 | Институт Молекулярной Генетики Российской Академии Наук (Имг Ран) | 2-AMINO-4-(β-HYDROXYETHYLAMINO)ANISOLE UNIFORMLY LABELED WITH TRITIUM |
| RU2309929C2 (en) * | 2005-11-15 | 2007-11-10 | Институт Молекулярной Генетики Российской Академии Наук (Имг Ран) | Chlorohexidine highly labeled with tritium |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| RU2089532C1 (en) * | 1995-03-31 | 1997-09-10 | Институт молекулярной генетики РАН | Method of preparing quaternary amine salts containing tritium labelled aromatic radical at nitrogen atom |
| RU2309929C2 (en) * | 2005-11-15 | 2007-11-10 | Институт Молекулярной Генетики Российской Академии Наук (Имг Ран) | Chlorohexidine highly labeled with tritium |
| RU2291142C1 (en) * | 2005-11-17 | 2007-01-10 | Институт Молекулярной Генетики Российской Академии Наук (Имг Ран) | 2-AMINO-4-(β-HYDROXYETHYLAMINO)ANISOLE UNIFORMLY LABELED WITH TRITIUM |
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