SU686308A1 - P-bromophenylamide of benzoylpyrotaric acid possessing antiinflammating activity - Google Patents
P-bromophenylamide of benzoylpyrotaric acid possessing antiinflammating activity Download PDFInfo
- Publication number
- SU686308A1 SU686308A1 SU782624970A SU2624970A SU686308A1 SU 686308 A1 SU686308 A1 SU 686308A1 SU 782624970 A SU782624970 A SU 782624970A SU 2624970 A SU2624970 A SU 2624970A SU 686308 A1 SU686308 A1 SU 686308A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- bromophenylamide
- activity
- benzoylpyrotaric
- antiinflammating
- acid possessing
- Prior art date
Links
- 230000000694 effects Effects 0.000 title description 2
- 239000002253 acid Substances 0.000 title 1
- 239000003814 drug Substances 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 9
- -1 benzoyl pyruvic acid p-bromophenylamide Chemical compound 0.000 description 8
- VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 4
- 229960002895 phenylbutazone Drugs 0.000 description 4
- 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
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 210000003097 mucus Anatomy 0.000 description 3
- 235000019698 starch Nutrition 0.000 description 3
- 239000008107 starch Substances 0.000 description 3
- WDFQBORIUYODSI-UHFFFAOYSA-N 4-bromoaniline Chemical compound NC1=CC=C(Br)C=C1 WDFQBORIUYODSI-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- GCXNJAXHHFZVIM-UHFFFAOYSA-N 2-phenylfuran Chemical compound C1=COC(C=2C=CC=CC=2)=C1 GCXNJAXHHFZVIM-UHFFFAOYSA-N 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- SDNGDXDXVLZBLK-UHFFFAOYSA-N n-(4-bromophenyl)-2-oxopropanamide Chemical compound CC(=O)C(=O)NC1=CC=C(Br)C=C1 SDNGDXDXVLZBLK-UHFFFAOYSA-N 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 201000008383 nephritis Diseases 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 231100000046 skin rash Toxicity 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
Landscapes
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
Изобретение относитс к области синтеза биологически активного нового соединени , конкретно п-бромфениламида бензоилпировиноградной кислоты , про вл квдей противовоспалительную активность. This invention relates to the synthesis of a biologically active novel compound, specifically benzoyl pyruvic acid p-bromophenylamide, which has anti-inflammatory activity.
Указанное вещество предполагаетс использовать в медицине.This substance is intended to be used in medicine.
Известно соединение фенилбутазон . 1,2-дифенил-4-н-бутилпиразолидиндион-3 ,5, про вл ющее противовоспалительную активность l.The compound phenylbutazone is known. 1,2-diphenyl-4-n-butylpyrazolidinedione-3, 5, showing anti-inflammatory activity l.
Недостатком известного соединени вл етс наличие побочных влений таких как тошнота, боли в области желудка, кожные сыпи, нефриты при его применении.A disadvantage of the known compound is the presence of side effects such as nausea, pain in the stomach, skin rashes, nephritis during its use.
Цель изобретени заключаетс в расширении средств воздействи на живой организм.The purpose of the invention is to expand the means of action on a living organism.
Посталенна цель достигаетс получением нового соединени структурной формулы CgH5COCHj(CO)2NHCgH Br.A permanent goal is achieved by obtaining a new compound of the structural formula CgH5COCHj (CO) 2NHCgH Br.
Указанное соединение получают путем взаимодействи 5-фенилфуран ..2,3-диона с п-броманилином в среде сухого толуола при комнатной температуре . После удалени растворител продукт выдел ют известными приемамThe compound is obtained by reacting 5-phenylfuran, 2,3-dione with p-bromoaniline in dry toluene at room temperature. After removal of the solvent, the product is isolated according to known methods.
Полученный п-бромфениламид бензоилпировиноградной кислоты представл ет собой желтое кристаллическое вещество, труднорастворимое в толуоле , бензоле, хлороформе, хорошо растворимое в этилацетате.The resulting p-bromophenylamide benzoyl pyruvic acid is a yellow crystalline substance, hardly soluble in toluene, benzene, chloroform, soluble in ethyl acetate.
Пример. п-Бромфениламид бензоилпировиноградной кислоты. К 1,74 г (0,01 г-моль) 5-фенилфуран0 -2,3-диона в 200 мл сухого толуола приливают 1,71 г (0,01 г-моль) п-броманилина в 75 мл толуола. После удалени растворител получают 3,39 г (98%) продукта ацетонитрил Example. Benzoyl pyruvic acid p-bromophenylamide. To 1.74 g (0.01 gmol) of 5-phenylfuran0 -2,3-dione, 1.71 g (0.01 gmol) of p-bromoaniline in 75 ml of toluene are poured into 200 ml of dry toluene. After removal of the solvent, 3.39 g (98%) of the product acetonitrile are obtained.
5 с т.пл. 164.5 pp. 164.
Вычислено,%: N 4,03; Вг 23,12.Calculated,%: N 4.03; Br 23.12.
Н. ВгМОз N. VGMOZ
Найдено,%: N 4,20, В г 22,87.Found,%: N 4.20, G 22.87.
ИК-спектр полученного соединени IR spectrum of the obtained compound
0 соответствует придаваемой ему структуре , в спектре присутствуют линии 1710 см (валентные колебани амидного карбонила), 1615 см (валентные колебани кетонного карбонила), 5 3410 см (валентные колебани аминогруппы ) .0 corresponds to the structure imparted to it, the spectrum contains lines of 1710 cm (stretching vibrations of amide carbonyl), 1615 cm (stretching vibrations of ketone carbonyl), 5 3410 cm (stretching vibrations of the amino group).
ИК-спектр п-бромфениламида бензоилпировиноградной кислоты идентичен спектрам ариламидов ароилпировино0 градных кислот.The IR spectrum of p-bromophenylamide benzoyl pyruvic acid is identical to the spectra of aryl amides of aroyl pyruvic acids.
в УФ-спектре длинноволновый максимум поглощени находитс в области 437 нм.in the UV spectrum, the long-wavelength absorption maximum is in the region of 437 nm.
п-Бромфениламид пировиноградной кислоты был исследован при внутрибршинном введении на белых мышах (тетрагибриды ) и белых крысах (линии Вистар). Дл оценки противовоспалительного действи используют модель формалинового воспалени . Величину отека определ ют онкометрическим методом А.С.Сал мона (1958) через 3 ч и 6 ч после введени флорогенного агента. Эталоном сравнени служит фенилбутазон (30 мг/кг). Препарат испытан в дозе 50 мг/кгPyruvic acid p-bromphenylamide was studied by intra-intramuscular administration in white mice (tetrahybrids) and white rats (Wistar strain). A formalin-inflammatory model is used to evaluate the anti-inflammatory effect. The magnitude of the edema is determined by the A. S. Sal mona method (1958) 3 hours and 6 hours after the administration of the fluorogenic agent. The comparison standard is phenylbutazone (30 mg / kg). The drug is tested at a dose of 50 mg / kg
(1/10 от ЛДд .(1/10 of LDD.
Исследуемое соединение вводили в дозе 50 мг/кг в виде взвеси в 2%-ной крахмальной слизи за 0,5 чThe investigated compound was administered at a dose of 50 mg / kg as a suspension in 2% starch mucus for 0.5 h
до и через 3 ч после введени флорогенного агента. Контрольной группе животных вводили эквиобъемные количества 2%-ной крахмальной слизи в те же промежутки времени.before and 3 hours after administration of the fluorogenic agent. The control group of animals was injected with an equivalent amount of 2% starch mucus at the same time intervals.
Исследовани показали, что п-бромфениламид бензоилпировиноградной кислоты обладает выраженным противовоспалительным действием, не уступающим таковому фенилбутазона на модели экспериментального формалинового .воспалени .Studies have shown that benzoylpyruvic acid p-bromophenylamide has a pronounced anti-inflammatory effect, which is not inferior to that of phenylbutazone on a model of experimental formalin inflammation.
При этом новое соединение малотоксично: величина его ЛД-р на белых мышах при внутрибрюшинном -введении превыиает 50 мг/кг.At the same time, the new compound is of low toxicity: the value of its LD-r in white mice with intraperitoneal injection exceeds 50 mg / kg.
В таблице приведены сравнительные данные известного и предлагаемого соединений.The table shows the comparative data of the known and proposed compounds.
п-Бромфениламид бензоилпировиноградной кислотыp-Bromphenylamide benzoyl pyruvic acid
Фенилбутазон (бутадион)Phenylbutazone (Butadion)
Контроль - слизь 2%-на крахмсшьна Control - mucus 2% starch
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782624970A SU686308A1 (en) | 1978-06-06 | 1978-06-06 | P-bromophenylamide of benzoylpyrotaric acid possessing antiinflammating activity |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU782624970A SU686308A1 (en) | 1978-06-06 | 1978-06-06 | P-bromophenylamide of benzoylpyrotaric acid possessing antiinflammating activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU686308A1 true SU686308A1 (en) | 1981-10-15 |
Family
ID=20768625
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU782624970A SU686308A1 (en) | 1978-06-06 | 1978-06-06 | P-bromophenylamide of benzoylpyrotaric acid possessing antiinflammating activity |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU686308A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6608196B2 (en) | 2001-05-03 | 2003-08-19 | Galileo Pharmaceuticals, Inc. | Process for solid supported synthesis of pyruvate-derived compounds |
| US11453640B2 (en) * | 2018-03-21 | 2022-09-27 | Northwestern University | Small molecules for disrupting the super elongation complex and inhibiting transcription elongation for cancer therapy |
-
1978
- 1978-06-06 SU SU782624970A patent/SU686308A1/en active
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6608196B2 (en) | 2001-05-03 | 2003-08-19 | Galileo Pharmaceuticals, Inc. | Process for solid supported synthesis of pyruvate-derived compounds |
| US11453640B2 (en) * | 2018-03-21 | 2022-09-27 | Northwestern University | Small molecules for disrupting the super elongation complex and inhibiting transcription elongation for cancer therapy |
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