SU655310A3 - Method of obtaining imidazole derivatives - Google Patents
Method of obtaining imidazole derivativesInfo
- Publication number
- SU655310A3 SU655310A3 SU762386215A SU2386215A SU655310A3 SU 655310 A3 SU655310 A3 SU 655310A3 SU 762386215 A SU762386215 A SU 762386215A SU 2386215 A SU2386215 A SU 2386215A SU 655310 A3 SU655310 A3 SU 655310A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- imidazole derivatives
- methyl
- obtaining
- imidazole
- solution
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНОГО ИМИДАЗОЛА(54) METHOD OF OBTAINING DERIVATIVE IMIDAZOL
Бывают из воды, получа 4-этоксикарбонил5-этокснметилнмндазол (6,1 г), т. ил. 143-144°С .They come from water to give 4-ethoxycarbonyl5-ethoxymethylnmndazole (6.1 g), t. Il. 143-144 ° C.
В. 4-Этоксикарбон11Л-5-этокснмс-П Л11мидазол (6,0 г) раствор ют в 48%-ном водном растворе бромистоводородной кислоты (650 мл) и кип т т с обратным холодильником в присутствии цпстсамингидро.хлорида (3,4 г) 17 ч. Растворитель отгон ют досуха и выпавший осадок перскристаллнзовывают из смеси бутанол/эфир (15:85), получа 4-карбокси - (амипоэтилтио)метил -имидазол дигидробромид (10,9 г), т. пл. 219-220°С.B. 4-Ethoxycarbon-11L-5-ethoxnms-PL11-imidazole (6.0 g) is dissolved in a 48% aqueous solution of hydrobromic acid (650 ml) and heated under reflux in the presence of cpstamine hydrochloride (3.4 g ) 17 hours. The solvent is distilled off to dryness and the precipitated precipitate is recrystallized from butanol / ether (15:85) to give 4-carboxy- (amipoethylthio) methyl-imidazole dihydrobromide (10.9 g), mp. 219-220 ° C.
Г. Раствор 4-карбокси-5- 2-(амииоэтилтио )-метил - имидазола дигидробромнда (1,0 г) в 10% (по объему) серной кислоты (24 мл) подвергают в течение 3 ч электролизу при посто нном токе 1,0 А и напр жении 8-10 В на вращающемс ртутном катоде и платиновом аноде, разделенных пористым диском.D. A solution of 4-carboxy-5- 2- (amioethylthio) -methyl-imidazole dihydrobromide (1.0 g) in 10% (by volume) sulfuric acid (24 ml) is subjected to electrolysis at a constant current for 3 hours at a constant current of 1, 0 A and a voltage of 8–10 V on a rotating mercury cathode and platinum anode, separated by a porous disk.
Регулировкой рН до 9-10 с помощью карбоната кали (8,3 г) и упаривание. раствора досуха получают остаток, который экстрагируют гор чим изопропанолом. После отгонки растворител получают 5-гидроксиметил - (аминоэтилтио) - метил имидазол (0,4 г).Adjusting the pH to 9-10 with potassium carbonate (8.3 g) and evaporation. dry solution of the residue, which is extracted with hot isopropanol. After distilling off the solvent, 5-hydroxymethyl - (aminoethylthio) - methyl imidazole (0.4 g) is obtained.
Д. К раствору 5-гидроксиметил-4- 2 (аминоэтилтио)-метил -имидазола (0,4 г) в этаноле (3 мл) прибавл ют этанольиый раствор д метил циандитиоиммдокарбоната (0,3 г) и перемешивают 2 ч при 15°С. Упариванием растворител получают в видеD. To a solution of 5-hydroxymethyl-4-2 (aminoethylthio) -methyl-imidazole (0.4 g) in ethanol (3 ml) was added an ethanol solution of methyl cyanthioimoimdocarbonate (0.3 g) and stirred for 2 hours at 15 ° WITH. Evaporation of the solvent is obtained in the form
масла 5-метил-Ы-циан-К - {2- 5-гидроксиметил-4 - пмидазолил)-метплтио - этил}кзотиомочевину , к которой затем прибавл ют избыток этанольного раствора метиламина (7 г). После 70 ч перемешивани реакциоппую смесь очищают при помощи тонкослойной хроматографии, получа 0,1 г целевого продукта в виде масла. Структура продукта устаиовлсиа с помощью ЯМРспектра в ДоО.5-methyl-L-cyano-K - {2-5-hydroxymethyl-4-pmidazolyl) methylthio-ethyl} kothiourea oil, to which an excess of ethanolic methylamine solution (7 g) is then added. After 70 hours of stirring, the reaction mixture is purified by thin layer chromatography to obtain 0.1 g of the expected product in the form of an oil. Product structure of ustaiovlsya by means of NMR spectrum in Doo.
Ф о р : у л а и 3 о б р е т е и и F o r: u l a and 3 o b e t e u u
Способ получени производного имидазола формулыThe method of obtaining the imidazole derivative of the formula
,-л-с мs-m
СН С}1 -№1-rtCH C} 1 - №1-rt
(U(U
NH-CH,NH-CH,
от л и ч а ю П1;и и с тем, что амин формулыfrom l and h and p1; and with the fact that the amine of the formula
«с.К,,CH5.-S-CHjCH,--NH, fllj"S.K ,, CH5.-S-CHjCH, - NH, fllj
//
подвергают взаимодействию е диметил-Nциандитиоимидокарбонатом и полученное соединение обрабатывают метиламином споследующим выделением целевого продукта .subjected to interaction with dimethyl-Ncyandithioimidocarbonate and the resulting compound is treated with methylamine followed by isolation of the target product.
Источники информации, прин тые во внимание при экспертизе 1. Кратка химическа энциклопеди . М., 1963, т. 2, с. 877.Sources of information taken into account in the examination 1. Brief chemical encyclopedia. M., 1963, t. 2, p. 877.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB31968/75A GB1565647A (en) | 1975-07-31 | 1975-07-31 | Pharmacologically active compounds 4-substituted-imidazole-5-methanols |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU655310A3 true SU655310A3 (en) | 1979-03-30 |
Family
ID=10331071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762386215A SU655310A3 (en) | 1975-07-31 | 1976-07-30 | Method of obtaining imidazole derivatives |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5219663A (en) |
| AR (1) | AR213100A1 (en) |
| AT (1) | AT356668B (en) |
| AU (1) | AU508262B2 (en) |
| BE (1) | BE843840A (en) |
| CA (1) | CA1075702A (en) |
| CS (1) | CS203054B2 (en) |
| DD (1) | DD125205A5 (en) |
| DE (1) | DE2634430A1 (en) |
| DK (1) | DK316376A (en) |
| ES (1) | ES450309A1 (en) |
| FI (1) | FI762191A (en) |
| FR (1) | FR2319341A1 (en) |
| GB (1) | GB1565647A (en) |
| GR (1) | GR61114B (en) |
| HU (1) | HU174068B (en) |
| IL (1) | IL50006A0 (en) |
| LU (1) | LU75495A1 (en) |
| NL (1) | NL7608505A (en) |
| NO (1) | NO762659L (en) |
| OA (1) | OA05405A (en) |
| PH (1) | PH13417A (en) |
| PT (1) | PT65377B (en) |
| RO (1) | RO72312B (en) |
| SE (1) | SE7608478L (en) |
| SU (1) | SU655310A3 (en) |
| ZA (1) | ZA763686B (en) |
| ZM (1) | ZM9676A1 (en) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR62452B (en) | 1977-04-20 | 1979-04-12 | Ici Ltd | Preparation process of guanidine derivatives |
| US4165378A (en) | 1977-04-20 | 1979-08-21 | Ici Americas Inc. | Guanidine derivatives of imidazoles and thiazoles |
| US4112234A (en) | 1977-08-22 | 1978-09-05 | Bristol-Myers Company | Imidazolylmethylthioethyl alkynyl guanidines |
| USRE31588E (en) * | 1977-06-03 | 1984-05-22 | Bristol-Myers Company | Imidazolylmethylthioethyl alkynyl guanidines |
| US4233302A (en) | 1977-12-23 | 1980-11-11 | Glaxo Group Limited | Amine derivatives and pharmaceutical compositions containing them |
| EP0008596A1 (en) * | 1978-09-04 | 1980-03-19 | DEVINTER Europe S.A. Société anonyme dite: | Preparation of 4-hydroxymethyl-imidazole derivatives from the corresponding 4-imidazole carboxylic acid esters |
| US4200760A (en) * | 1978-09-26 | 1980-04-29 | Bristol-Myers Company | Imidazolylalkylthioalkylamino-ethylene derivatives |
| JPS5914460B2 (en) * | 1978-12-27 | 1984-04-04 | 相互薬工株式会社 | Production method of cimetidine, an anti-H↓2 receptor |
| CN103288742A (en) * | 2013-06-04 | 2013-09-11 | 四川百利药业有限责任公司 | Preparation method for high-purity ingavirin raw material |
| US20230349922A1 (en) | 2020-08-11 | 2023-11-02 | Université De Strasbourg | H2 Blockers Targeting Liver Macrophages for the Prevention and Treatment of Liver Disease and Cancer |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA938556A (en) * | 1970-06-25 | 1973-12-18 | Smith Kline And French Laboratories Limited | Pharmaceutical compositions containing thiourea derivatives |
-
1975
- 1975-07-31 GB GB31968/75A patent/GB1565647A/en not_active Expired
-
1976
- 1976-06-21 ZA ZA763686A patent/ZA763686B/en unknown
- 1976-07-06 BE BE168682A patent/BE843840A/en not_active IP Right Cessation
- 1976-07-09 PH PH18667A patent/PH13417A/en unknown
- 1976-07-09 IL IL50006A patent/IL50006A0/en unknown
- 1976-07-13 DK DK316376A patent/DK316376A/en unknown
- 1976-07-16 PT PT65377A patent/PT65377B/en unknown
- 1976-07-20 FR FR7622069A patent/FR2319341A1/en active Granted
- 1976-07-21 CS CS764839A patent/CS203054B2/en unknown
- 1976-07-22 CA CA257,589A patent/CA1075702A/en not_active Expired
- 1976-07-23 ZM ZM96/76A patent/ZM9676A1/en unknown
- 1976-07-27 GR GR51356A patent/GR61114B/en unknown
- 1976-07-27 SE SE7608478A patent/SE7608478L/en unknown
- 1976-07-27 AT AT552376A patent/AT356668B/en not_active IP Right Cessation
- 1976-07-29 LU LU75495A patent/LU75495A1/xx unknown
- 1976-07-30 NL NL7608505A patent/NL7608505A/en not_active Application Discontinuation
- 1976-07-30 DE DE19762634430 patent/DE2634430A1/en not_active Withdrawn
- 1976-07-30 AR AR264157A patent/AR213100A1/en active
- 1976-07-30 JP JP51092242A patent/JPS5219663A/en active Pending
- 1976-07-30 HU HU76SI1532A patent/HU174068B/en unknown
- 1976-07-30 FI FI762191A patent/FI762191A/fi not_active Application Discontinuation
- 1976-07-30 DD DD194154A patent/DD125205A5/xx unknown
- 1976-07-30 NO NO762659A patent/NO762659L/no unknown
- 1976-07-30 SU SU762386215A patent/SU655310A3/en active
- 1976-07-30 AU AU16447/76A patent/AU508262B2/en not_active Expired
- 1976-07-30 ES ES450309A patent/ES450309A1/en not_active Expired
- 1976-07-31 OA OA55903A patent/OA05405A/en unknown
- 1976-07-31 RO RO87167A patent/RO72312B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE843840A (en) | 1977-01-06 |
| RO72312A (en) | 1984-03-15 |
| AU1644776A (en) | 1978-02-02 |
| FR2319341B1 (en) | 1979-01-12 |
| HU174068B (en) | 1979-10-28 |
| PH13417A (en) | 1980-03-30 |
| ATA552376A (en) | 1979-10-15 |
| GR61114B (en) | 1978-09-13 |
| NL7608505A (en) | 1977-02-02 |
| OA05405A (en) | 1981-02-28 |
| ZA763686B (en) | 1977-05-25 |
| DD125205A5 (en) | 1977-04-06 |
| ZM9676A1 (en) | 1977-07-21 |
| NO762659L (en) | 1977-02-01 |
| AU508262B2 (en) | 1980-03-13 |
| IL50006A0 (en) | 1976-09-30 |
| DK316376A (en) | 1977-02-01 |
| DE2634430A1 (en) | 1977-02-10 |
| RO72312B (en) | 1984-03-31 |
| LU75495A1 (en) | 1977-03-03 |
| CA1075702A (en) | 1980-04-15 |
| SE7608478L (en) | 1977-02-01 |
| JPS5219663A (en) | 1977-02-15 |
| FI762191A (en) | 1977-02-01 |
| PT65377B (en) | 1978-01-19 |
| GB1565647A (en) | 1980-04-23 |
| ES450309A1 (en) | 1977-12-01 |
| CS203054B2 (en) | 1981-02-27 |
| PT65377A (en) | 1976-08-01 |
| FR2319341A1 (en) | 1977-02-25 |
| AT356668B (en) | 1980-05-12 |
| AR213100A1 (en) | 1978-12-15 |
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