RU2030402C1 - S-(2-pyridiniumethyl)-n-methylthiuronium diiodide showing radioprotective activity - Google Patents
S-(2-pyridiniumethyl)-n-methylthiuronium diiodide showing radioprotective activity Download PDFInfo
- Publication number
- RU2030402C1 RU2030402C1 SU4953383A RU2030402C1 RU 2030402 C1 RU2030402 C1 RU 2030402C1 SU 4953383 A SU4953383 A SU 4953383A RU 2030402 C1 RU2030402 C1 RU 2030402C1
- Authority
- RU
- Russia
- Prior art keywords
- methylthiuronium
- diiodide
- pyridiniumethyl
- showing
- radioprotective
- Prior art date
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- 230000004223 radioprotective effect Effects 0.000 title claims description 10
- 150000001875 compounds Chemical class 0.000 abstract description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract description 4
- ICEDWTMMAQLCTQ-UHFFFAOYSA-M 1-(2-iodoethyl)pyridin-1-ium;iodide Chemical compound [I-].ICC[N+]1=CC=CC=C1 ICEDWTMMAQLCTQ-UHFFFAOYSA-M 0.000 abstract description 3
- KQJQICVXLJTWQD-UHFFFAOYSA-N N-Methylthiourea Chemical compound CNC(N)=S KQJQICVXLJTWQD-UHFFFAOYSA-N 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 2
- 239000000718 radiation-protective agent Substances 0.000 abstract description 2
- 239000000126 substance Substances 0.000 abstract description 2
- 239000003153 chemical reaction reagent Substances 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 241001465754 Metazoa Species 0.000 description 8
- 239000003814 drug Substances 0.000 description 5
- XDVMCVGTDUKDHL-UHFFFAOYSA-N [amino(2-azaniumylethylsulfanyl)methylidene]azanium;dibromide Chemical compound Br.Br.NCCSC(N)=N XDVMCVGTDUKDHL-UHFFFAOYSA-N 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
- 231100000053 low toxicity Toxicity 0.000 description 2
- 230000004083 survival effect Effects 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- RCGTWCOBGMGDKS-UHFFFAOYSA-N N1=CC=CC=C1.CNC(=S)N Chemical compound N1=CC=CC=C1.CNC(=S)N RCGTWCOBGMGDKS-UHFFFAOYSA-N 0.000 description 1
- 230000003471 anti-radiation Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 231100001224 moderate toxicity Toxicity 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000003537 radioprotector Effects 0.000 description 1
- 235000000891 standard diet Nutrition 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Pyridine Compounds (AREA)
Abstract
Description
Изобретение относится кк новому химическому соединению, в частности к S-(2-пиридинийэтил)-N-метилтиурония дииодиду формулы 1
В качестве аналога по структуре и действию взят известный в медицине радиопротектор β-аминоэтилизотиурония бромид (АЭТ) [1] . Радиозащитное действие препарата для облученных животных к 30-м суткам составляет 50%. The radioprotector β-aminoethylisothiuronium bromide (AET), known in medicine, was taken as an analogue in structure and action [1]. The radioprotective effect of the drug for irradiated animals by the 30th day is 50%.
Цель изобретения - получение нового соединения из класса замещенных тиурониевых солей, обладающего умеренной токсичностью и выраженным радиозащитным свойством. The purpose of the invention is to obtain a new compound from the class of substituted thiuronium salts, which has moderate toxicity and pronounced radioprotective property.
Поставленная цель достигается получением соединения формулы I путем взаимодействия N(2-иодэтил)пиридиний иодида с метилтиомочевиной при нагревании в присутствии спирта по схеме:
Из патентной и технической литературы неизвестно получение соединения формулы I, обладающего радиозащитной активностью, что позволяет считать данное предложение обладающим "Существенными отличиями".This goal is achieved by obtaining the compounds of formula I by the interaction of N (2-iodoethyl) pyridinium iodide with methylthiourea when heated in the presence of alcohol according to the scheme:
From the patent and technical literature it is not known to obtain a compound of formula I having radioprotective activity, which allows us to consider this proposal as having "Significant differences".
П р и м е р 1. 10 ммоль (3,6 г) N(2-иодэтил)пиридиний иодид и 10 ммоль (0,9 г) метилтиомочевины нагревают в 20 мл спирте в течение 0,5 ч. После охлаждения содержимого колбы выпадают кристаллы желтого цвета S-(2-пиридинийэтил)-N-метилтиурония иодида. Выход 100% (4,5 г). Перекристаллизовывали из спирта. Example 1 10 mmol (3.6 g) N (2-iodoethyl) pyridinium iodide and 10 mmol (0.9 g) methylthiourea are heated in 20 ml of alcohol for 0.5 h. After cooling the contents of the flask yellow crystals of S- (2-pyridinium ethyl) -N-methylthiuronium iodide precipitate. Yield 100% (4.5 g). Recrystallized from alcohol.
Тал. - 208-210оС. Мол.м. 451,11.Tal. - 208-210 about S. Mol.m. 451.11.
Найдено,%: S 7,00; I 56,43. Found,%: S 7.00; I 56.43.
C9H15I2N3S.C 9 H 15 I 2 N 3 S.
Вычислено,%: S 7,40; I 56,26. Calculated,%: S 7.40; I 56.26.
ПМР ДМСО dI6 (б.м.д.): 2,86 S (3Н, СН3); 4,90 Т (2Н, СН2); 3,44 Т (2Н, СН2); 9,00 м (8H, Аr, NH). 1 H NMR DMSO dI 6 (bpm): 2.86 S (3H, CH 3 ); 4.90 T (2H, CH 2 ); 3.44 T (2H, CH 2 ); 9.00 m (8H, Ar, NH).
Pадиозащитную активность (РЗА) исследуемого соединения изучали по тесту 30-дневной выживаемости облученных животных на мышах-самцах F1(СВАхС57Bl)6. Доза облучения 7 Гр (ЛД100/30) при мощности дозы 08 Гр/мин.Radioprotective activity (RPA) of the test compound was studied by the 30-day survival test of irradiated animals in male mice F 1 (CBAxC 57 Bl) 6 . The radiation dose of 7 Gy (LD 100/30 ) at a dose rate of 08 Gy / min.
Препарат вводили в водном растворе внутрибрюшинно за 15, 30, 60 мин. до облучения животных в дозировке 120 мг/кг. Эталоном служил β-аминоэтилизотиурония бромид (АЭТ), введенный аналогично в оптимальной защитной дозировке 280 мг/кг. Контролем служили животные, облученные в той же дозе без предварительной инъекции вещества. В опытах использовалось 270 животных. Облученных животных содержали на стандартном рационе вивария и вели за ними наблюдение в течение 30 сут. The drug was administered intraperitoneally in an aqueous solution for 15, 30, 60 minutes. before irradiation of animals in a dosage of 120 mg / kg. The reference was β-aminoethylisothiuronium bromide (AET), administered analogously at an optimal protective dosage of 280 mg / kg. The control was animals irradiated at the same dose without prior injection of the substance. In the experiments 270 animals were used. Irradiated animals were kept on a standard diet of vivarium and monitored for 30 days.
Исследования показали (см. табл.), что S-бисметилен(N-пиридиний)-N-метилтиуро- ния дийодид РЗА, превышающий таковую эталонного препарата: выживаемость облученных животных к 30 суткам составила соответственно 60 и 50% при введении за 15 мин при 90% гибели животных в контрольной группе. Исследованное соединение малотоксично (по шкале К. Сидорова, 1973) 1/2 ЛД50 = 140 мг/кг.Studies have shown (see table) that S-bismethylene (N-pyridinium) -N-methylthiuronium RPA diiodide, exceeding that of the reference preparation: the survival rate of irradiated animals by 30 days was 60 and 50%, respectively, after administration for 15 min at 90% of the death of animals in the control group. The tested compound has low toxicity (according to the scale of K. Sidorov, 1973) 1/2 LD 50 = 140 mg / kg.
В связи с тем, что заявляемое соединение малотоксично, обладает выраженной радиозащитной активностью, превышающей таковую эталонного препарата, оно может найти применение в качестве радиопрофилак- тического средства. Due to the fact that the claimed compound has low toxicity, has a pronounced radioprotective activity that exceeds that of the reference drug, it can find application as a radioprophylactic agent.
Claims (1)
проявляющий радиозащитную активность.S- (2-Pyridiniumethyl) -N-methylthiuronium diiodide of the formula
showing radioprotective activity.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU4953383 RU2030402C1 (en) | 1991-04-22 | 1991-04-22 | S-(2-pyridiniumethyl)-n-methylthiuronium diiodide showing radioprotective activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU4953383 RU2030402C1 (en) | 1991-04-22 | 1991-04-22 | S-(2-pyridiniumethyl)-n-methylthiuronium diiodide showing radioprotective activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| RU2030402C1 true RU2030402C1 (en) | 1995-03-10 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU4953383 RU2030402C1 (en) | 1991-04-22 | 1991-04-22 | S-(2-pyridiniumethyl)-n-methylthiuronium diiodide showing radioprotective activity |
Country Status (1)
| Country | Link |
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| RU (1) | RU2030402C1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2018043259A1 (en) * | 2016-08-31 | 2019-08-08 | 富士フイルム株式会社 | Coloring composition, lithographic printing plate precursor, lithographic printing plate preparation method, and compound |
-
1991
- 1991-04-22 RU SU4953383 patent/RU2030402C1/en active
Non-Patent Citations (1)
| Title |
|---|
| Машковский М.Д. Лекарственные средства, М.: Медицина, 1986, часть 2, с.189. * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPWO2018043259A1 (en) * | 2016-08-31 | 2019-08-08 | 富士フイルム株式会社 | Coloring composition, lithographic printing plate precursor, lithographic printing plate preparation method, and compound |
| US11117364B2 (en) | 2016-08-31 | 2021-09-14 | Fujifilm Corporation | Color developing composition, lithographic printing plate precursor, method for producing lithographic printing plate, and compound |
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