SU1114676A1 - 1,5-diphenyl-3-oxyl-4-methylsulfonyl-2,5-dihydropyrrol-2-one as intermediate product for synthesis of 1,5-diphenyl-3-hydroxyethylamino-4-methylsulfonyl-2,5-dihydropyrrol-2-one having antiaggregate effect against thrombocytes - Google Patents
1,5-diphenyl-3-oxyl-4-methylsulfonyl-2,5-dihydropyrrol-2-one as intermediate product for synthesis of 1,5-diphenyl-3-hydroxyethylamino-4-methylsulfonyl-2,5-dihydropyrrol-2-one having antiaggregate effect against thrombocytes Download PDFInfo
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- SU1114676A1 SU1114676A1 SU833606631A SU3606631A SU1114676A1 SU 1114676 A1 SU1114676 A1 SU 1114676A1 SU 833606631 A SU833606631 A SU 833606631A SU 3606631 A SU3606631 A SU 3606631A SU 1114676 A1 SU1114676 A1 SU 1114676A1
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- USSR - Soviet Union
- Prior art keywords
- diphenyl
- dihydropyrrol
- methylsulfonyl
- hydroxyethylamino
- synthesis
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- 230000000694 effects Effects 0.000 title claims description 9
- GCZNEPIHSCNIGX-UHFFFAOYSA-N 4-(2-hydroxyethylamino)-3-methylsulfonyl-1,2-diphenyl-2H-pyrrol-5-one Chemical compound C1(=CC=CC=C1)N1C(C(=C(C1C1=CC=CC=C1)S(=O)(=O)C)NCCO)=O GCZNEPIHSCNIGX-UHFFFAOYSA-N 0.000 title claims description 5
- 230000015572 biosynthetic process Effects 0.000 title claims description 5
- 238000003786 synthesis reaction Methods 0.000 title claims description 5
- 230000002744 anti-aggregatory effect Effects 0.000 title claims 2
- XFSJRYNTZUUCHM-UHFFFAOYSA-N 4-hydroxy-3-methylsulfonyl-1,2-diphenyl-2h-pyrrol-5-one Chemical compound CS(=O)(=O)C1=C(O)C(=O)N(C=2C=CC=CC=2)C1C1=CC=CC=C1 XFSJRYNTZUUCHM-UHFFFAOYSA-N 0.000 title description 3
- 239000013067 intermediate product Substances 0.000 title description 3
- 210000001772 blood platelet Anatomy 0.000 title 1
- 239000003146 anticoagulant agent Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 description 8
- 230000000702 anti-platelet effect Effects 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- XQYZDYMELSJDRZ-UHFFFAOYSA-N papaverine Chemical compound C1=C(OC)C(OC)=CC=C1CC1=NC=CC2=CC(OC)=C(OC)C=C12 XQYZDYMELSJDRZ-UHFFFAOYSA-N 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 229930008281 A03AD01 - Papaverine Natural products 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 229960001789 papaverine Drugs 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 150000003239 pyrrolones Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 1
- 235000009754 Vitis X bourquina Nutrition 0.000 description 1
- 235000012333 Vitis X labruscana Nutrition 0.000 description 1
- 240000006365 Vitis vinifera Species 0.000 description 1
- 235000014787 Vitis vinifera Nutrition 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- JLVNWDAQUSEIAI-UHFFFAOYSA-N ethyl 3-methylsulfonyl-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CS(C)(=O)=O JLVNWDAQUSEIAI-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 231100000816 toxic dose Toxicity 0.000 description 1
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
1.5-Дифенил-3-окси-4-метштсульфонш1-2 ,5-дигидро1шррол-2-он формулы dHj Ogон СбН5-С о СбНу в качестве промежуточного продукта дл синтеза 1,5-дифенил-З-оксиэтиламино-4-метилсульфоннл-2 ,5-дигидрошфрол 2-она , обладающего антиагре- . г гантной активгностью против тромбоцитов . (Л С1.5-Diphenyl-3-hydroxy-4-metstsulfonsh-1-2, 5-dihydro-1-shrol-2-one of the formula dHj Ogon SbH5-C o SbHu as an intermediate product for the synthesis of 1,5-diphenyl-3-hydroxyethylamino-4-methylsulfonnl-2 , 5-dihydroshfrol 2-she with antiaggre-. A gantny active against platelets. (Ls
Description
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а I Изобретение относитс к новому производному пирролона, конкретно к 1,5-дифенил-3-окси-4-метнпсульфонил-2 ,5-дигкдропиррол-2-ону формулы ЙН,02 у который может использоватьс в качестве промежуточного продукта дл синтеза 1,5-дифенил-З-оксиэтиламино .4-метилсульфонил-2,5-дигидропиррол-2-она , обладающего антиагрегантной активностью против тромбоцитов. Наиболее близким по структуре к соединению (Г) вл етс 1.3-дифени -3-ацетокси-4-этилоксикарбонил-2,5-дигидропиррол-2-он ij формулы odoCHj с,н,осо Однако сведени о его использовании в качестве промежуточного в;оединени дл вещества, обладающего антиагрегантной активностью против тромбоцитов, в литературе отсутствую Цель изобретени - изыскание в р ду производных пирролона соединени которое может быть использовано в качестве промежуточного дл синтеза вещества, обладающего антиагрегантно активностью против тромбоцитов. Указанна цель достигаетс П1 именением 1 ,5-дифенил-3-окси-4-метилсульфонил-2 ,5-дигидропиррол-2-она формулы (I) в качестве промежуточного продукта дл синтеза 1,5-дифенил-З-оксиэтиламино-4-метилсульфонил-2 ,5-дигидропиррол-2-она, обладаю щего антиагрегантной активностью против тромбоцитов. Соединение формулы (1) получают конденсацией бензальдегида, анилина и этилового эфира метилсульфонилпиро виноградной кислоты при комнатной температуре с послед тощей обработкой полученного продукта 2 и. сол ной кислотой. Соединение (I) представл ет собой б1;сцнетное кристаллическое 76 вещество.растворимое в диоксане, диметилсульфоксиде. Пример 1. 1,5-Дифeнил-3-oкcи-4-мeтилcyльфoнил-2 ,5-дигидропиррол-2-он . К 3,88 г (0,02 моль) этилового эфира метилсульфонилпировиноградной кислоты в 18 мл диоксана добавл ют 2,12 г (0,02 моль) бензальдегида и 1,86 г (0,02 моль) анилина. Реакционную смесь вьщерживают при комнатной температуре в течение 48 ч, выпавщиё кристаллы отфильтровывают и обрабатывают 2 и. сол ной кислотой. Получают 6,1 (74,2%) целевого продукта , т.пл. 217-8с с разложением (из спирта). Найдено, %: С 62,12; Н 4,49, N 4,14; S 9,87. С Н, Вычислено, %: С 62,01J Н 4,55; N 4,25; S 9,73. В ИК-спектре соединени (I) присутствуют полосы поглощени сульфонильной группы при 1150 и 1315 см , полоса поглощени при 1650 см обусловленна наличием в цикле двойной св зи, поглощение лактонного карбонила при 1730, 1630 , полосы поглощени при 3100 и 3335 счет.гидроксильной группы. В ПМР-спектре вещества, сн том в растворе дейтерированного диметилсульфоксида , кроме мультиплета ароматических протонов с центром при 7,28 М.Д., присутствует синглет метинового протона в положении 5 при 6,15, а также синглет метильной группы при 2,68 м.д. I Соединение(I) может использоватьс в качестве промежуточного .дл получени 1,5-дифенил-З-оксиэтиламино-4-метилсульфонил-2 ,5-дигидропиррол-2-она , про вл ющего антиагрегантную активность против тромбоцитов. 1,5-Дифенил-3-оксиэтиламино-4-метилсульфонил-2 ,5-дигидропиррол-2-он получают взаимодействием 1,5-дифенил-3-окси-4-метилсульфонил-2 ,5-дигидропиррол-2-она с этаноламином при комнатной температуре в диоксане. П р и м е р .2. 1,5-Дифeнил-3-oкcиэтилaминo-4-фeнилcyльфoнил-2 ,5-дигидpoпиppoл-2-oн . К 3,29 г (0,01 моль) 1,5-фенил-З-окси-4-метилсульфонил-2 ,5-дигидропиррол-2-она в 30 мл диоксана добавл ют 0,61 г (0,01 моль) этаноламина. а-11146 Реакционную смесь вьщерживают при комнатной температуре в течение 20 ч. Затем вьтавшие кристаллы отфильтровывают . Ползтают 3,3 г (89%) целевого продукта, Т.Ш1. 179-180°С с разло- j жением (из спирта). , Найдено, %: С 61,20; Н 5,79; N7,33; S 8,53. . CjgH , . Вычислецо, %: С 61,13i Н 5,62; ю N 7,50i S 8,58. 1,5-Дифенил-3-оксизтиламино-4-фенилсульфонил-2 ,5-дигищ опиррол-2-он про вл ет высокую антиагрегант76 4 ную активность против тромбоцитов, под его вли нием агрегаци тромброцитов снижаетс на 29,2%, а под вли нием известного препарата папаверина, обладающего вьюокЫ антиагрегантной активностью против тромбоцитов на 18,8%. При исследовании острой токсичиости установлено, что средн токсическа доза LD соединени (I) равна 880 (792,8-976,8) мг/кг, а папаверина 27 ,(25,1-30,3), т.е. соадинекие (J) менее токсично, чем эталон сравнени (в 32,6 раз).a I The invention relates to a new derivative of pyrrolone, specifically to 1,5-diphenyl-3-hydroxy-4-metnpsulfonyl-2, 5-digkdropyrrol-2-one of the formula YH 02, which can be used as an intermediate product for the synthesis of 1, 5-diphenyl-3-hydroxyethylamino .4-methylsulfonyl-2,5-dihydropyrrol-2-one, which has antiplatelet activity against platelets. The closest in structure to the compound (D) is the 1.3-dipheny-3-acetoxy-4-ethyloxycarbonyl-2,5-dihydropyrrol-2-one ij of the formula odoCHj s, n, oso However, information about its use as an intermediate in; Compounds for a substance with antiplatelet activity against platelets are absent in the literature. The purpose of the invention is to find a compound in a series of pyrrolone derivatives that can be used as an intermediate for the synthesis of a substance possessing antiplatelet activity against platelets. This goal is achieved by P1 by the name of 1, 5-diphenyl-3-hydroxy-4-methylsulfonyl-2, 5-dihydropyrrol-2-one of formula (I) as an intermediate product for the synthesis of 1,5-diphenyl-3-hydroxyethylamino-4- methylsulfonyl-2, 5-dihydropyrrol-2-one, which has antiplatelet activity against platelets. The compound of formula (1) is obtained by condensation of benzaldehyde, aniline, and methylsulfonylpyro grape acid ethyl ester at room temperature, followed by treatment of the resulting product 2 and. hydrochloric acid. Compound (I) is b1; 76% crystalline substance soluble in dioxane, dimethyl sulfoxide. Example 1. 1,5-Diphenyl-3-oxy-4-methylsulfonyl-2, 5-dihydropyrrol-2-one. To 2.88 g (0.02 mol) of methyl sulphonyl pyruvic acid ethyl ester in 18 ml of dioxane were added 2.12 g (0.02 mol) of benzaldehyde and 1.86 g (0.02 mol) of aniline. The reaction mixture is held at room temperature for 48 hours, the precipitated crystals are filtered and treated with 2 and. hydrochloric acid. Get 6,1 (74,2%) of the desired product, so pl. 217-8c with decomposition (from alcohol). Found,%: C 62,12; H 4.49, N 4.14; S 9.87. C H, Calculated,%: C 62.01J, H 4.55; N 4.25; S 9.73. The absorption spectrum of the sulfonyl group at 1150 and 1315 cm, the absorption band at 1650 cm due to the presence of a double bond in the cycle, the absorption of lactone carbonyl at 1730, 1630, the absorption band at 3100 and 3335 counts of the hydroxyl group are present in the IR spectrum of compound (I) . In the PMR spectrum of a substance, removed in a solution of deuterated dimethyl sulfoxide, in addition to the multiplet of aromatic protons centered at 7.28 MD, the singlet of the methine proton is present at position 5 at 6.15, and the singlet of the methyl group at 2.68 m .d I Compound (I) can be used as an intermediate to obtain 1,5-diphenyl-3-hydroxyethylamino-4-methylsulfonyl-2, 5-dihydropyrrol-2-one, which exhibits antiplatelet activity against platelets. 1,5-Diphenyl-3-hydroxyethylamino-4-methylsulfonyl-2, 5-dihydropyrrol-2-one is obtained by reacting 1,5-diphenyl-3-hydroxy-4-methylsulfonyl-2, 5-dihydropyrrol-2-one with ethanolamine at room temperature in dioxane. PRI me R. 2. 1,5-Diphenyl-3-oxyethylamino-4-phenylsulfonyl-2, 5-dihydropopyrol-2-one. To 3.29 g (0.01 mol) of 1,5-phenyl-3-hydroxy-4-methylsulfonyl-2, 5-dihydropyrrol-2-one in 30 ml of dioxane was added 0.61 g (0.01 mol) ethanolamine. a-11146 The reaction mixture is held at room temperature for 20 hours. Then, the crystals which have entered are filtered off. Crawl 3.3 g (89%) of the desired product, T.Sh1. 179-180 ° C with decomposition (from alcohol). Found:% C 61.20; H 5.79; N7.33; S 8.53. . CjgH,. Calcd.,%: C, 61.13; H, 5.62; No 7,50i S 8,58. 1,5-Diphenyl-3-oxystilamino-4-phenylsulfonyl-2, 5-digyshirprol-2-one exhibits a high antiaggregant76 4th activity against platelets, under its influence, the aggregation of thrombrocytes decreases by 29.2%, and under by the influence of the well-known drug papaverine, which possesses antiplatelet activity against platelets by 18.8%. In the study of acute toxicity, it was found that the average toxic dose of LD of compound (I) is 880 (792.8-976.8) mg / kg, and papaverine 27, (25.1-30.3), i.e. soadine (J) is less toxic than the reference standard (32.6 times).
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Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU833606631A SU1114676A1 (en) | 1983-03-31 | 1983-03-31 | 1,5-diphenyl-3-oxyl-4-methylsulfonyl-2,5-dihydropyrrol-2-one as intermediate product for synthesis of 1,5-diphenyl-3-hydroxyethylamino-4-methylsulfonyl-2,5-dihydropyrrol-2-one having antiaggregate effect against thrombocytes |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU833606631A SU1114676A1 (en) | 1983-03-31 | 1983-03-31 | 1,5-diphenyl-3-oxyl-4-methylsulfonyl-2,5-dihydropyrrol-2-one as intermediate product for synthesis of 1,5-diphenyl-3-hydroxyethylamino-4-methylsulfonyl-2,5-dihydropyrrol-2-one having antiaggregate effect against thrombocytes |
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| Publication Number | Publication Date |
|---|---|
| SU1114676A1 true SU1114676A1 (en) | 1984-09-23 |
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| Application Number | Title | Priority Date | Filing Date |
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| SU833606631A SU1114676A1 (en) | 1983-03-31 | 1983-03-31 | 1,5-diphenyl-3-oxyl-4-methylsulfonyl-2,5-dihydropyrrol-2-one as intermediate product for synthesis of 1,5-diphenyl-3-hydroxyethylamino-4-methylsulfonyl-2,5-dihydropyrrol-2-one having antiaggregate effect against thrombocytes |
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| SU (1) | SU1114676A1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5098927A (en) * | 1989-05-15 | 1992-03-24 | Fujisawa Pharmaceutical Co., Ltd. | Antiretroviral agent, method of use thereas, and method of preparation |
| RU2195449C2 (en) * | 1995-06-28 | 2002-12-27 | Байер Акциенгезельшафт | 2,4,5-trisubstituted phenylketoenoles, intermediate compounds for their synthesis, method and agent for control of insects and spiders based on thereof |
| WO2003030897A1 (en) * | 2001-10-03 | 2003-04-17 | Ucb, S.A. | Pyrrolidinone derivatives |
-
1983
- 1983-03-31 SU SU833606631A patent/SU1114676A1/en active
Non-Patent Citations (1)
| Title |
|---|
| 1. Joannic М., Humbert D., Peason М. Acids diaryl-.1,5-oxo-2-pyrrolidyl-4-carboxyligues. G.r.Acad. sci., 1972, p. 275, 1, 45-48. * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5098927A (en) * | 1989-05-15 | 1992-03-24 | Fujisawa Pharmaceutical Co., Ltd. | Antiretroviral agent, method of use thereas, and method of preparation |
| RU2195449C2 (en) * | 1995-06-28 | 2002-12-27 | Байер Акциенгезельшафт | 2,4,5-trisubstituted phenylketoenoles, intermediate compounds for their synthesis, method and agent for control of insects and spiders based on thereof |
| WO2003030897A1 (en) * | 2001-10-03 | 2003-04-17 | Ucb, S.A. | Pyrrolidinone derivatives |
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