SU794006A1 - 2-methyl-3-alkyl-(aralkyl)-thiocarbonyl-4-aryl-5-oxo-1,4-dihydroindeno/1,2-b/-puridine derivatives possessing coronarodilating activity - Google Patents

2-methyl-3-alkyl-(aralkyl)-thiocarbonyl-4-aryl-5-oxo-1,4-dihydroindeno/1,2-b/-puridine derivatives possessing coronarodilating activity Download PDF

Info

Publication number
SU794006A1
SU794006A1 SU772527679A SU2527679A SU794006A1 SU 794006 A1 SU794006 A1 SU 794006A1 SU 772527679 A SU772527679 A SU 772527679A SU 2527679 A SU2527679 A SU 2527679A SU 794006 A1 SU794006 A1 SU 794006A1
Authority
SU
USSR - Soviet Union
Prior art keywords
dihydroindeno
oxo
methyl
coronarodilating
puridine
Prior art date
Application number
SU772527679A
Other languages
Russian (ru)
Inventor
Бригита Авридовна Виганте
Ян-Волдемар Янович Озол
Гунта Освальдовна Силениеце
Агрис Адольфович Кименис
Гунар Янович Дубур
Original Assignee
Ордена Трудового Красного Знамениинститут Органического Синтеза Анлатвийской Ccp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ордена Трудового Красного Знамениинститут Органического Синтеза Анлатвийской Ccp filed Critical Ордена Трудового Красного Знамениинститут Органического Синтеза Анлатвийской Ccp
Priority to SU772527679A priority Critical patent/SU794006A1/en
Application granted granted Critical
Publication of SU794006A1 publication Critical patent/SU794006A1/en

Links

Landscapes

  • Plural Heterocyclic Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Description

НИЛ - 4 - фенил-5 - оксо - 1,4 - дигидроиндено {1,2-&) пиридин. Смесь 1,17 г (0,005 моль) 2-бензилидениндандиона-1 ,3 и 1,04 г (0,005 моль) S-бензилового эфира р-аминотиокротоновой кислоты кип т т в 5 мл лед ной уксусной кислоты 5 мин. После охлаждени  выдел ет темно-красное вещество, выход 1,23 г (58%), т. пл. 226-228°С (из уксусной кислоту ). Найдено, %: С 76,68; Н 4,97; N 3,29; S 8,01. CayHaiiNOsS. Вычислено, %: С 76,57; Н 5,00; N 3,31; S 7,57. УФ-спектр, Амако, нм: 203, 238 (плечо), 268, 355, 495. ИК-спектр, см-1; vco 1645; VN-H 3300. Пример 2. 2-Метил-З-этилтиокарбонил-4 - фенил-5 - оксо - 1,4 - дигидроиндено (1,2-&) пиридин. Синтез провод т аналогично примеру 1. Выход 87%, т. пл. 248-249°С. Найдено, %: С 73,00; Н 5,61; N4,01; S 9,00. C22Hi9NO2S. Вычислено, %: С 73,10; Н 5,30; N 3,88; S 8,87. УФ-спектр, Хмакс, нм: 203, 238, 268, 355, 495. ИК-спектр: см-: , 1680; VN-H 3260. Пример 3. 2-Метил-З-бензилтиокарбонил-4-р-оксифенил - 5-оксо-1,4-дигидроиндено ( 1,2-6) пиридин. Синтез провод т аналогично примеру 1. Выход 78%, т. пл. 247°С. Найдено, %: С 73,48; Н 4,84; N 3,30; 57,25. С27Н21НОз5. Вычислено, %: С 73,78; Н 4,82; N 3,19; S 7,30. УФ-спектр, Лмакс, нм: 203, 220 (плечо), 262,305 (плечо), 460. ИК-спектр, CM-I: , 1680; VN-H 3210. Пример 4. 2-Метил-З-этилтиокарбонил4-о-оксифенил-5 - оксо - 1,4-дигидроиндено (1,2-Ь) пиридин. Синтез провод т аналогично примеру 1. Выход 79%, т. пл. 225-22ГС. Найдено, %: С 69,92; Н 4,90; N 3,95; S 8,23. CazHiaNOsS. Вычислено, %: С 70,00; Н 5,97; N 3,71; S 8,50. УФ-спектр, ;.макс, нм: 203, 220 (плечо), 263, 460. ИК-спектр, CM-I: , 1690; VN-H 3220. Пример 5. 2-Метил-З-этилтиокарбонил4-л-нитрофенил - 5-оксо-1,4-дигидроиндено (1,2-Ь) пиридин. Синтез провод т аналогично примеру 1. Выход 74%, т. пл. 238°С. Найдено, %: С 65,20; Н 4,59; N 6,54; S 7,65. C22HigN2O4S. Вычислено, %: С 65,01; Н 4,46; N 6,89; S 7,89. УФ-спектр, Ямакс, нм: 203, 263, 295 (плечо ) , 340, 495. ИК-спектр, CM-I: , 1645; VN-H 3280. Пример 6. 2-Метил-З-этилтиокарбонил-о-нитрофенил - 5-оксо-1,4-дигидроиндено (1,2-&) пиридин. Синтез провод т аналогично примеру 1. Выход 82%, т. пл. 221°С. Найдено, %: С 64,50; Н 4,47; N 6,50; S 7,28. C22Hi8H2O4C. Вычислено, %: С 65,01; Н 4,46; N 6,89; S 7,89. УФ-спектр, Хмакс, нм: 203, 266, 345, 495. ИК-спектр, CM-I: , 1680; VN-H 3320.NIL - 4 - phenyl-5 - oxo - 1,4 - dihydroindeno {1,2 - &) pyridine. A mixture of 1.17 g (0.005 mol) of 2-benzylidenide danedione-1, 3 and 1.04 g (0.005 mol) of p-aminothio-protonic acid S-benzyl ester is boiled in 5 ml of glacial acetic acid for 5 minutes. After cooling, it gives off a dark red substance, yield 1.23 g (58%), so pl. 226-228 ° C (from acetic acid). Found,%: C 76.68; H 4.97; N 3.29; S 8.01. CayHaiiNOsS. Calculated,%: C 76.57; H 5.00; N 3.31; S 7.57. UV spectrum, Amaco, nm: 203, 238 (shoulder), 268, 355, 495. IR spectrum, cm-1; vco 1645; VN-H 3300. Example 2. 2-Methyl-3-ethylthiocarbonyl-4-phenyl-5-oxo-1,4-dihydroindeno (1,2-)) pyridine. The synthesis is carried out analogously to example 1. Yield 87%, mp. 248-249 ° C. Found,%: C 73.00; H 5.61; N4.01; S 9.00. C22Hi9NO2S. Calculated,%: C 73.10; H 5.30; N 3.88; S 8.87. UV spectrum, hmax, nm: 203, 238, 268, 355, 495. IR spectrum: cm-:, 1680; VN-H 3260. Example 3. 2-Methyl-3-benzylthiocarbonyl-4-p-hydroxyphenyl-5-oxo-1,4-dihydroindeno (1,2-6) pyridine. The synthesis is carried out analogously to example 1. Yield 78%, mp. 247 ° C. Found,%: C 73.48; H 4.84; N 3.30; 57.25. C27H21NOZ5. Calculated,%: C 73.78; H 4.82; N 3.19; S 7.30. UV spectrum, Lmax, nm: 203, 220 (shoulder), 262.305 (shoulder), 460. IR spectrum, CM-I:, 1680; VN-H 3210. Example 4. 2-Methyl-3-ethylthiocarbonyl4-o-hydroxyphenyl-5-oxo-1,4-dihydroindeno (1,2-b) pyridine. Synthesis is carried out analogously to example 1. Yield 79%, mp. 225-22GS. Found,%: C 69.92; H 4.90; N 3,95; S 8.23. CazHiaNOsS. Calculated,%: C 70.00; H 5.97; N 3.71; S 8.50. UV spectrum; max. Nm: 203, 220 (shoulder), 263, 460. IR spectrum, CM-I:, 1690; VN-H 3220. Example 5. 2-Methyl-3-ethylthiocarbonyl4-l-nitrophenyl-5-oxo-1,4-dihydroindeno (1,2-b) pyridine. The synthesis is carried out analogously to example 1. Yield 74%, mp. 238 ° C. Found,%: C 65.20; H 4.59; N 6.54; S 7.65. C22HigN2O4S. Calculated,%: C 65.01; H 4.46; N 6.89; S 7.89. UV spectrum, Yamax, nm: 203, 263, 295 (shoulder), 340, 495. IR spectrum, CM-I:, 1645; VN-H 3280. Example 6. 2-Methyl-3-ethylthiocarbonyl-o-nitrophenyl-5-oxo-1,4-dihydroindeno (1,2-)) pyridine. The synthesis is carried out analogously to example 1. Yield 82%, mp. 221 ° C. Found,%: C 64.50; H 4.47; N 6.50; S 7.28. C22Hi8H2O4C. Calculated,%: C 65.01; H 4.46; N 6.89; S 7.89. UV spectrum, Hmax, nm: 203, 266, 345, 495. IR spectrum, CM-I:, 1680; VN-H 3320.

1.2-Метил-3-этилтиокарбонил-4 - фенил-5оксо-1 ,4-дигидроиндено (1,2-Ь) пиридин.1.2-Methyl-3-ethylthiocarbonyl-4-phenyl-5oxo-1, 4-dihydroindeno (1,2-b) pyridine.

11.2-Метил-З-бензилтиокарбонил - 4 - феНИЛ-5-ОКСО - 1,4-дигидроиндено( 1,2-6) пиридин .11.2-Methyl-3-benzylthiocarbonyl-4-phenyl-5-OXO-1,4-dihydroindeno (1,2-6) pyridine.

111.2-Метил-З - бензилтиокарбонил - 4-ооксифенил-5-оксо-1 ,4 - дигидроиндено (1,2-6) пиридин.111.2-Methyl-3-benzylthiocarbonyl-4-oxyphenyl-5-oxo-1, 4-dihydroindeno (1,2-6) pyridine.

1У.2-Метил-3-этилтиокарбонил-4-о - оксифенил-5-оксо - 1,4-дигидроиндено(1,2-6)пиридин .1U.2-Methyl-3-ethylthiocarbonyl-4-o-hydroxyphenyl-5-oxo-1,4-dihydroindeno (1,2-6) pyridine.

У.2-Метил-3-этилтиокарбонил - 4-л-нитрофенил-5-оксо-1 ,4 - дигидроиндено( 1,2-6) пиридин .U.2-Methyl-3-ethylthiocarbonyl - 4-l-nitrophenyl-5-oxo-1, 4 - dihydroindeno (1,2-6) pyridine.

У1.2-Метил-3-этилтиокарбонил - 4-о - нитрофенил-5-оксо - 1,4-дигидроиндено( 1,2-6) пиридин.U1.2-Methyl-3-ethylthiocarbonyl - 4-o-nitrophenyl-5-oxo-1,4-dihydroindeno (1,2-6) pyridine.

Claims (2)

1.I. Chem. Soc., 1949, 2134.1.I. Chem. Soc., 1949, 2134. 2.I. Am. Chem. Soc., 1945, 67, 1017.2.I. Am. Chem. Soc., 1945, 67, 1017.
SU772527679A 1977-09-12 1977-09-12 2-methyl-3-alkyl-(aralkyl)-thiocarbonyl-4-aryl-5-oxo-1,4-dihydroindeno/1,2-b/-puridine derivatives possessing coronarodilating activity SU794006A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
SU772527679A SU794006A1 (en) 1977-09-12 1977-09-12 2-methyl-3-alkyl-(aralkyl)-thiocarbonyl-4-aryl-5-oxo-1,4-dihydroindeno/1,2-b/-puridine derivatives possessing coronarodilating activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
SU772527679A SU794006A1 (en) 1977-09-12 1977-09-12 2-methyl-3-alkyl-(aralkyl)-thiocarbonyl-4-aryl-5-oxo-1,4-dihydroindeno/1,2-b/-puridine derivatives possessing coronarodilating activity

Publications (1)

Publication Number Publication Date
SU794006A1 true SU794006A1 (en) 1981-01-07

Family

ID=20726259

Family Applications (1)

Application Number Title Priority Date Filing Date
SU772527679A SU794006A1 (en) 1977-09-12 1977-09-12 2-methyl-3-alkyl-(aralkyl)-thiocarbonyl-4-aryl-5-oxo-1,4-dihydroindeno/1,2-b/-puridine derivatives possessing coronarodilating activity

Country Status (1)

Country Link
SU (1) SU794006A1 (en)

Similar Documents

Publication Publication Date Title
ES468578A1 (en) Substituted phenylacetic acid derivatives and process for the preparation thereof
DE69418243D1 (en) N-heteroaryl-N'-phenylurea derivatives, their preparation and use
CA2192731A1 (en) Monohydrates of aminobenzenesulfonic acid derivatives and method for preparing thereof
ES487769A1 (en) Cycloalkylidenemethylphenylacetic acid derivatives and process for the preparation thereof
NO941977L (en) Indole derivatives, processes for their preparation, and medical use thereof
ES465137A1 (en) 1,4-dihydropyridine derivatives and process for preparation thereof
FI102178B (en) Process for the preparation of therapeutically useful 1,2,3,3a, 8,8a-hexahydro-1,3a, 8-trimethyl-pyrrolo [2,3-b] indol-5-yl derivative
CA2013087A1 (en) Carbonate derivatives of eseroline, a process for their preparation and their use as medicaments
SU794006A1 (en) 2-methyl-3-alkyl-(aralkyl)-thiocarbonyl-4-aryl-5-oxo-1,4-dihydroindeno/1,2-b/-puridine derivatives possessing coronarodilating activity
IL61261A (en) Pyridine and pyrimidine derivatives and pharmaceutical compositions containing them
Ellis et al. Synthesis of holomycin and derivatives
JPS5492946A (en) 2-aminomethylphenol derivative and its production
AU5782290A (en) 4,5-dihydro-6h-imidazo(4,5,1-ij)quinolin-6-one-6-oxime-0- sulfonic acid derivatives
DE3781879D1 (en) ANTHRACYCLINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS MEDICINAL PRODUCTS.
IE780279L (en) Imidazole derivatives
JPS5728046A (en) Preparation of 4-substituted indole
US4452982A (en) Process for the preparation of nitrogen-bridgehead condensed pyrimidine compounds, and pharmaceutical compositions containing them
SU656521A3 (en) Method of obtaining derivatives of thieno-(3,2-c)-pyridine or salts thereof
US4656169A (en) Tetracyclic spiro-hydantoin aldose reductase inhibitors and compositions
NO855383L (en) PROCEDURE FOR PIPERAZINE DERIVATIVES PREPARATION.
JPS55122785A (en) Preparation of benzopyranopyridine derivative
IE811209L (en) Indole acetic acid derivatives
JPS5540645A (en) Benzopyrone derivative
SU575349A1 (en) Method of obtaining arylsuphonamide derivatives of 1,2-dihydroquinoline
JPS5515426A (en) Pyranopyrrole derivative