RU2831253C1 - N-ETHYL-2-((3-OXO-6-(4-FLUOROPHENYL)-2-ETHYL-2,3-DIHYDROPYRIDAZIN-4-YL)AMINO)-4,5,6,7-TETRAHYDROBENZO[b]THIOPHENE-3-CARBOXIMIDE HYDRAZIDE, HAVING ANTIMICROBIAL ACTIVITY - Google Patents
N-ETHYL-2-((3-OXO-6-(4-FLUOROPHENYL)-2-ETHYL-2,3-DIHYDROPYRIDAZIN-4-YL)AMINO)-4,5,6,7-TETRAHYDROBENZO[b]THIOPHENE-3-CARBOXIMIDE HYDRAZIDE, HAVING ANTIMICROBIAL ACTIVITY Download PDFInfo
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- RU2831253C1 RU2831253C1 RU2024110377A RU2024110377A RU2831253C1 RU 2831253 C1 RU2831253 C1 RU 2831253C1 RU 2024110377 A RU2024110377 A RU 2024110377A RU 2024110377 A RU2024110377 A RU 2024110377A RU 2831253 C1 RU2831253 C1 RU 2831253C1
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- 230000000845 anti-microbial effect Effects 0.000 title claims abstract description 10
- -1 N-ethyl-2-((3-oxo-6-(4-fluorophenyl)-2-ethyl-2,3-dihydropyridazin-4-yl)amino)-4,5,6,7-tetrahydrobenzo[ b ]thiophene Chemical compound 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 abstract description 4
- 230000000694 effects Effects 0.000 abstract description 4
- 239000000126 substance Substances 0.000 abstract description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZQBAKBUEJOMQEX-UHFFFAOYSA-N phenyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OC1=CC=CC=C1 ZQBAKBUEJOMQEX-UHFFFAOYSA-N 0.000 description 6
- 229940125904 compound 1 Drugs 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229960000969 phenyl salicylate Drugs 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920001817 Agar Polymers 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 239000008272 agar Substances 0.000 description 2
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 241000191940 Staphylococcus Species 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 229940127554 medical product Drugs 0.000 description 1
- 230000000813 microbial effect Effects 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Abstract
Description
Изобретение относится к области органической химии, к новым биологически активным веществам класса замещенных пиридазин-3(2H)-онов, а именно к N-этил-2-((3-оксо-6-(4-фторфенил)-2-этил-2,3-дигидропиридазин-4-ил)амино)-4,5,6,7-тетрагидробензо[b]тиофен-3-карбоксимидгидразиду формулы:The invention relates to the field of organic chemistry, to new biologically active substances of the class of substituted pyridazin-3(2H)-ones, namely to N-ethyl-2-((3-oxo-6-(4-fluorophenyl)-2-ethyl-2,3-dihydropyridazin-4-yl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboximidohydrazide of the formula:
который обладает противомикробной активностью, что позволяет предположить его использование в медицине в качестве лекарственного средства с противомикробными свойствами.which has antimicrobial activity, which suggests its use in medicine as a drug with antimicrobial properties.
Аналогом по структуре заявляемому соединению является этиловый эфир 2-[(3-оксо-6-фенил-2-этил-2,3-дигидропиридазин-4-ил)амино]-4,5,6,7-тетрагидробензо[b]тиофен-3-карбоновой кислоты [S.A. Shipilovskikh, А.Е. Rubtsov, Russian Journal of Organic Chemistry, 2014, Vol. 50, No. 12, pp. 1853-1855, doi: 10.1134/S1070428014120288] формулы:A structural analogue of the claimed compound is ethyl ester of 2-[(3-oxo-6-phenyl-2-ethyl-2,3-dihydropyridazin-4-yl)amino]-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxylic acid [S.A. Shipilovskikh, A.E. Rubtsov, Russian Journal of Organic Chemistry, 2014, Vol. 50, No. 12, pp. 1853-1855, doi: 10.1134/S1070428014120288] of the formula:
Эталоном сравнения был выбран фенилсалицилат формулы:The comparison standard chosen was phenyl salicylate of the formula:
который широко применяется в лечебной практике и является аналогом по действию [Машковский М.Д. Лекарственные средства.- 16-е изд., перераб., испр. и доп. - М.: Новая волна, 2012. - c. 950].which is widely used in medical practice and is similar in action to [Mashkovsky M.D. Medicines. - 16th edition, revised, corrected and supplemented. - M.: Novaya Volna, 2012. - p. 950].
Задачей изобретения является поиск в ряду замещенных пиридазин-3(2H)-онов веществ с выраженным противомикробным действием.The objective of the invention is to search for substances with pronounced antimicrobial action in a series of substituted pyridazin-3(2H)-ones.
Поставленная задача достигается получением N-этил-2-((3-оксо-6-(4-фторфенил)-2-этил-2,3-дигидропиридазин-4-ил)амино)-4,5,6,7-тетрагидробензо[b]тиофен-3-карбоксимидгидразида, который обладает противомикробной активностью.The set task is achieved by obtaining N-ethyl-2-((3-oxo-6-(4-fluorophenyl)-2-ethyl-2,3-dihydropyridazin-4-yl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboximidohydrazide, which has antimicrobial activity.
Заявляемое соединение 1 синтезируют взаимодействием 2-((2-оксо-5-(4-фторфенил)фуран-3(2H)-илиден)амино)-4,5,6,7-тетрагидробензо[b]тиофен-3-карбонитрила с этилгидразином. Реакция протекает в безводном диоксане при перемешивании и температуре 90°С в течение 1 часа с последующим удалением растворителя и выделением целевого продукта известными методами по схеме:The claimed compound 1 is synthesized by the interaction of 2-((2-oxo-5-(4-fluorophenyl)furan-3(2H)-ylidene)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile with ethylhydrazine. The reaction takes place in anhydrous dioxane with stirring and a temperature of 90°C for 1 hour, followed by removal of the solvent and isolation of the target product by known methods according to the scheme:
Получение соединения 1: к 352 мг (0,001 моль) 2-((2-оксо-5-(4-фторфенил)фуран-3(2H)-илиден)амино)-4,5,6,7-тетрагидробензо[b]тиофен-3-карбонитрила добавили 5 мл безводного диоксана, 120 мг (0,002 моль) этилгидразина и перемешивали в течение 1 ч при 90°С. Раствор охлаждали до 0°С; выпавший осадок отфильтровывали и перекристаллизовывали из этанола. Выход 354 мг (78%), желтые кристаллы, т.пл. 194-195°С (этанол). Спектр 1Н ЯМР (CDCl3), δ, м.д.: 1.28 т (3Н, СН3), 1.45 т (3Н, СН3), 1.86 м (4Н, 2СН2), 2.51 м (2Н, СН2), 2.66 м (4Н, 2СН2), 4.35 кв (2Н, СН2), 4.65 уш. с (1H, NH), 7.15 м (2Н, Наром), 7.67 уш. с (1Н, NH), 7.77 м (2Н, Наром), 8.27 уш. с (Ш, NH), 8.66 уш. c(lH,NH). Спектр 13С ЯМР (CDC13), 8, м.д.: 9.1, 13.5,21.9, 23.1, 24.4, 24.5, 47.6, 67.1,101.2, 113.5, 115.6, 115.8, 128.1, 128.2, 129.1, 132.3, 132.3, 133.9, 138.7, 145.1, 148.0, 154.8. Найдено, %: С 60.72; Н 5.95; N 18.54; S, 7.01. C23H27FN6OS. Рассчитано, %: С 60.77; Н 5.99; N 18.49; S, 7.05.Preparation of compound 1: 5 ml of anhydrous dioxane and 120 mg (0.002 mol) of ethylhydrazine were added to 352 mg (0.001 mol) of 2-((2-oxo-5-(4-fluorophenyl)furan-3(2H)-ylidene)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carbonitrile and the mixture was stirred for 1 h at 90°C. The solution was cooled to 0°C; the formed precipitate was filtered off and recrystallized from ethanol. Yield 354 mg (78%), yellow crystals, mp 194-195°C (ethanol). 1 H NMR spectrum (CDCl 3 ), δ, ppm: 1.28 t (3H, CH 3 ), 1.45 t (3H, CH 3 ), 1.86 m (4H, 2CH 2 ), 2.51 m (2H, CH 2 ), 2.66 m (4H, 2CH 2 ), 4.35 sq (2H, CH 2 ), 4.65 br s (1H, NH), 7.15 m (2H, Harom ), 7.67 br s (1H, NH), 7.77 m (2H, Harom ), 8.27 br s (III, NH), 8.66 br s (lH, NH). 13C NMR ( CDCl3 ), δ, ppm: 9.1, 13.5, 21.9, 23.1, 24.4, 24.5, 47.6, 67.1, 101.2, 113.5, 115.6, 115.8, 128.1, 128.2, 129.1, 132.3, 132.3, 133.9, 138.7, 145.1, 148.0, 154.8. Found, %: C 60.72; H 5.95; N 18.54; S, 7.01. C 23H 27FN 6 OS. Calculated, %: C 60.77; H 5.99; N 18.49; S, 7.05.
Полученное соединение 1 представляет собой желтое кристаллическое вещество, растворимое в ДМСО, ацетоне, не растворимое в воде и гексане.The obtained compound 1 is a yellow crystalline substance, soluble in DMSO, acetone, insoluble in water and hexane.
Пример 2. Определение антимикробной активности проводили методом двукратных серийных разведений [Першин Г.Н. «Методы экспериментальной химиотерапии, 1971, с. 109] на музейных тест - культурах: Staphylococcus aurous, штамм 906; Escherichia coli, штамм 1257 (ФГБУ «Научный центр экспертизы средств медицинского применения», г. Москва). В опытах использовали 18 часовые агаровые тест - культуры (5*105 микробных тел в 1 мл среды). Для исследования брали раствор соединения 1 в диметилформамиде (ДМФА). Максимальная из испытанных концентраций была 1000 мкг/мл. Пробирки инкубировали при 37°С с последующим высевом через 20 часов и 7 суток в пробирки со скошенным мясопептонным агаром. Учет результатов проводили по наличию и характерному росту культур микроорганизмов на питательной среде. Эффект сравнивали с фенилсалицилатом.Example 2. Antimicrobial activity was determined by the method of two-fold serial dilutions [Pershin G.N. “Methods of Experimental Chemotherapy”, 1971, p. 109] on museum test cultures: Staphylococcus aurous, strain 906; Escherichia coli, strain 1257 (Federal State Budgetary Institution “Scientific Center for Expertise of Medical Products”, Moscow). 18-hour agar test cultures were used in the experiments (5*10 5 microbial bodies in 1 ml of medium). A solution of compound 1 in dimethylformamide (DMF) was used for the study. The maximum concentration tested was 1000 μg/ml. The test tubes were incubated at 37°C, followed by seeding after 20 hours and 7 days in test tubes with slanted meat-peptone agar. The results were recorded based on the presence and characteristic growth of microorganism cultures on the nutrient medium. The effect was compared with phenyl salicylate.
Результаты испытаний представлены в таблице:The test results are presented in the table:
Как видно из таблицы, заявляемое соединение 1 превышает по противомикробной активности препарат сравнения (фенилсалицилат) в 3 раза по отношению к St. aureus, а также проявляет выраженную активность к Е. coli, что показывает высокую эффективность соединения. Таким образом, N-этил-2-((3-оксо-6-(4-фторфенил)-2-этил-2,3-дигидропиридазин-4-ил)амино)-4,5,6,7-тетрагидробензо[b]тиофен-3-карбоксимидгидразид 1 проявляет более высокую активность по сравнению с эталоном сравнения, что делает возможным его использование для создания новых лекарственных средств целенаправленного действия.As can be seen from the table, the claimed compound 1 exceeds the comparison drug (phenyl salicylate) in antimicrobial activity by 3 times with respect to St. aureus, and also exhibits pronounced activity against E. coli, which demonstrates the high efficiency of the compound. Thus, N-ethyl-2-((3-oxo-6-(4-fluorophenyl)-2-ethyl-2,3-dihydropyridazin-4-yl)amino)-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboximidohydrazide 1 exhibits higher activity compared to the comparison standard, which makes it possible to use it to create new drugs with targeted action.
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| RU2831253C1 true RU2831253C1 (en) | 2024-12-03 |
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020102889A1 (en) * | 2018-11-19 | 2020-05-28 | Fouda Ahmed | 4,5,6,7-tetrahydro-l-benzothiophene modulators of retinoic acid receptor related (rar) orphan nuclear receptors (rors) |
| RU2808995C1 (en) * | 2023-03-31 | 2023-12-05 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | OBTAINING 2-((6-(2-METHOXYPHENYL)-3-OXO-2-ETHYL-2,3-DIHYDROPYRIDAZIN-4-YL)AMINO)-4,5,6,7-TETRAHYDROBENZO[b]THIOPHENE-3-CARBONITRILE WITH ANALGESIC ACTIVITY |
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2020102889A1 (en) * | 2018-11-19 | 2020-05-28 | Fouda Ahmed | 4,5,6,7-tetrahydro-l-benzothiophene modulators of retinoic acid receptor related (rar) orphan nuclear receptors (rors) |
| RU2808995C1 (en) * | 2023-03-31 | 2023-12-05 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" | OBTAINING 2-((6-(2-METHOXYPHENYL)-3-OXO-2-ETHYL-2,3-DIHYDROPYRIDAZIN-4-YL)AMINO)-4,5,6,7-TETRAHYDROBENZO[b]THIOPHENE-3-CARBONITRILE WITH ANALGESIC ACTIVITY |
Non-Patent Citations (1)
| Title |
|---|
| S.A. Shipilovskikh, А.Е. Rubtsov, Chemistry of Iminofurans. Recyclization of Ethyl 2-[2-Oxo-5-phenylfuran-3(2H)-ylideneamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate by the Action of Hydrazines Russian Journal of Organic Chemistry, Vol. 50, No. 12, pp. 1853-1855, 2014. * |
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