SU576043A3 - Способ получени -оксиметил-2-нитроимидазола - Google Patents
Способ получени -оксиметил-2-нитроимидазолаInfo
- Publication number
- SU576043A3 SU576043A3 SU7602306604A SU2306604A SU576043A3 SU 576043 A3 SU576043 A3 SU 576043A3 SU 7602306604 A SU7602306604 A SU 7602306604A SU 2306604 A SU2306604 A SU 2306604A SU 576043 A3 SU576043 A3 SU 576043A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nitroimidazole
- oxymethyl
- preparing
- evaporated
- residue
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
-
- 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
- C07D233/88—Nitrogen atoms, e.g. allantoin
-
- 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
- C07D233/91—Nitro radicals
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ а -ОКСИМЕТИЛ-2-НИТРОИМИДАЗОЛА
Изобретение относитс к способу получени нового соединени - а -оксиметил 2 - нитроимидазола , превосход щего по физиологической активности известные аналоги. Известный 1 способ получени 5 - (/3 -оксиалкил) - производных питроимидазола не позвол ет получить а - оксиалкильные производные. Предлагаемый способ получени о - оксимети.п 2 - нитронмидазола формулы I гг-но-с Д 1 If N02 СНз СНз заключаетс в кислотном гидролизе метоксипрюизводного формулы Сн., 2 Нз ОНз в интервале температур от до комнатной температуры с выделением целевого продукта. П р и м е р. К раствору 35 г 2 - амино - 5 (I метокси - 1 - метил) - этил) - 1 - метилимидазола в 75 мл воды добавл ют 120 мл фторборной кислоты, охлаждают до -20° С, в течение 15 мин при размешивании прибавл ют раствор 10 г нитрита натри в 40мл ноды, выдерживают 15 мин при (-10) - (-20)° С, выливают в смесь 29 г медного порошка, 95,2 г нигрита натри и 1400 мл воды и интенсилно перемешивают 1,5 час, барботиру одповременно через реакционную смесь азот. После фильтровани добавл ют сол ную кислоту до рН 2,5, барботируют азот еще 30 мин, зкстрагируют этилацетатом, промывают экстракты 10;гНым водным раствором бикарбоната натри и водой, сушат сульфатом натри , выпаривают , кристаллизуют остаток из бензола и хроматографируют на колонне, выдел 5,9 г 5 4 (1 - окси - 1 - метил) - этил - 1 - метилпитроимидазола ,т.пл. 160-162° С. Бензольный матоП1ый раствор после кристаллизации упаривают досуха, хроматографируют остаток на силикагеле, элюиру бензолом, содержащим 5% зтилацетата 1ю объему, собирают фракции с Rf 0,70 (тонкослойна хроматографи на силикагеле), упаривают, перекристаллизовывают остаток из смеси диэтилового и петролейного эфиров и по)гучают 0,6 г 5 - 1(1 - метокси - 1 метил) - этил - 1 -метил 2 нитроимидазола, т.пл. 120-121 С. Фракции с Rf 0,43 упаривают, иерекристаллизовывают остаток из бензола и получают 2,03 г назвалного соепииеии , т.пл. 160- 162° С.
К 0,6 г полученного вещества добавл ют 60 мл 1 н. сол ной кислоты, нагревают при ОС до полного растворени , перемешивают 10 мин, упаривают в вакууме, перекристаллизовывают остаток из бензола и но.пучают 0,350 г целевого соединени , т.пл. 160-162° С.
Claims (1)
1. Патент Бельгии Г 741692, Kn.C07d, 14.11.69.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1684/75A GB1480192A (en) | 1975-01-15 | 1975-01-15 | 1-methyl-2-nitro-imidazole-5-methanol derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU576043A3 true SU576043A3 (ru) | 1977-10-05 |
Family
ID=9726232
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7602306604A SU576043A3 (ru) | 1975-01-15 | 1976-01-14 | Способ получени -оксиметил-2-нитроимидазола |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US4041168A (ru) |
| JP (1) | JPS5195069A (ru) |
| AR (1) | AR207804A1 (ru) |
| AT (1) | ATA13576A (ru) |
| AU (1) | AU8787575A (ru) |
| BE (1) | BE837595A (ru) |
| CA (1) | CA1062716A (ru) |
| CH (1) | CH609050A5 (ru) |
| DD (1) | DD123744A5 (ru) |
| DE (1) | DE2600538C3 (ru) |
| DK (1) | DK153839C (ru) |
| ES (1) | ES444324A1 (ru) |
| FI (1) | FI753726A (ru) |
| FR (1) | FR2297623A1 (ru) |
| GB (1) | GB1480192A (ru) |
| GR (1) | GR59991B (ru) |
| IE (1) | IE42462B1 (ru) |
| IL (1) | IL48751A0 (ru) |
| IN (1) | IN141389B (ru) |
| LU (1) | LU74172A1 (ru) |
| NL (1) | NL175413C (ru) |
| NO (1) | NO760113L (ru) |
| NZ (1) | NZ179762A (ru) |
| PL (1) | PL98602B1 (ru) |
| PT (1) | PT64695B (ru) |
| RO (1) | RO69138A (ru) |
| SE (1) | SE422204B (ru) |
| SU (1) | SU576043A3 (ru) |
| ZA (1) | ZA758017B (ru) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4395341A (en) * | 1977-07-21 | 1983-07-26 | G. D. Searle & Co. | Use of metronidazole in oil recovery |
| DE3070778D1 (en) * | 1979-08-11 | 1985-07-25 | Bayer Ag | Antimycotic agents with enhanced release of the active ingredients |
| US4957918A (en) * | 1988-06-09 | 1990-09-18 | Leonard Bloom | Topical treatment of blepharitis |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3065133A (en) * | 1956-09-28 | 1962-11-20 | Rhone Poulenc Sa | Imidazoles for the control of histomoniasis |
| DE1470102A1 (de) * | 1963-11-27 | 1969-05-29 | Merck & Co Inc | 2-Hydroxymethyl-5-nitroimidazole und Verfahren zu deren Herstellung |
| US3472864A (en) * | 1964-03-18 | 1969-10-14 | Merck & Co Inc | 2-carbonyl-5-nitroimidazoles |
| NL124627C (ru) * | 1964-08-12 | |||
| GB1051388A (ru) * | 1964-11-17 | |||
| US3584007A (en) * | 1968-09-16 | 1971-06-08 | Merck & Co Inc | Preparation of 1-substituted-2-hydroxymethyl - 5-nitroimidazoles employing chilorinated benzenes as the reaction medium |
| NL143227B (nl) * | 1968-11-15 | 1974-09-16 | Lepetit Spa | Werkwijze ter bereiding van imidazoolderivaten met bactericide werking. |
| US3652579A (en) * | 1969-06-26 | 1972-03-28 | Hoffmann La Roche | 1-methyl-2-substituted 5-nitroimidazoles |
| US3634446A (en) * | 1969-10-06 | 1972-01-11 | Hoffmann La Roche | 1-methyl-2-isopropyl-5-nitroimidazole and water soluble salts thereof |
| DE2229248C3 (de) * | 1971-07-30 | 1980-03-27 | Gruppo Lepetit S.P.A., Mailand (Italien) | 5-Iminomethyl-2-nitroimidazoI-Derivate und Verfahren zu deren Herstellung |
| US3828064A (en) * | 1972-10-25 | 1974-08-06 | Dow Chemical Co | Method of preparing 1,5-disubstituted-2-nitroimidazoles |
-
1975
- 1975-01-15 GB GB1684/75A patent/GB1480192A/en not_active Expired
- 1975-12-20 GR GR49653A patent/GR59991B/el unknown
- 1975-12-24 AU AU87875/75A patent/AU8787575A/en not_active Expired
- 1975-12-29 IL IL48751A patent/IL48751A0/xx unknown
- 1975-12-29 US US05/644,382 patent/US4041168A/en not_active Expired - Lifetime
- 1975-12-29 ZA ZA00758017A patent/ZA758017B/xx unknown
- 1975-12-31 FI FI753726A patent/FI753726A/fi not_active Application Discontinuation
- 1975-12-31 IN IN2428/CAL/75A patent/IN141389B/en unknown
-
1976
- 1976-01-01 AR AR261930A patent/AR207804A1/es active
- 1976-01-08 IE IE30/76A patent/IE42462B1/en unknown
- 1976-01-08 DE DE2600538A patent/DE2600538C3/de not_active Expired
- 1976-01-12 AT AT13576A patent/ATA13576A/de not_active IP Right Cessation
- 1976-01-13 NL NLAANVRAGE7600284,A patent/NL175413C/xx not_active IP Right Cessation
- 1976-01-13 LU LU74172A patent/LU74172A1/xx unknown
- 1976-01-13 RO RO7684482A patent/RO69138A/ro unknown
- 1976-01-14 DK DK012976A patent/DK153839C/da not_active IP Right Cessation
- 1976-01-14 SE SE7600341A patent/SE422204B/xx not_active IP Right Cessation
- 1976-01-14 DD DD190802A patent/DD123744A5/xx unknown
- 1976-01-14 CH CH42376A patent/CH609050A5/xx not_active IP Right Cessation
- 1976-01-14 CA CA243,508A patent/CA1062716A/en not_active Expired
- 1976-01-14 PT PT64695A patent/PT64695B/pt unknown
- 1976-01-14 SU SU7602306604A patent/SU576043A3/ru active
- 1976-01-14 NZ NZ179762A patent/NZ179762A/xx unknown
- 1976-01-14 NO NO760113A patent/NO760113L/no unknown
- 1976-01-15 BE BE163537A patent/BE837595A/xx not_active IP Right Cessation
- 1976-01-15 ES ES444324A patent/ES444324A1/es not_active Expired
- 1976-01-15 FR FR7600995A patent/FR2297623A1/fr active Granted
- 1976-01-15 PL PL1976186558A patent/PL98602B1/pl unknown
- 1976-01-16 JP JP51003956A patent/JPS5195069A/ja active Granted
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