SU637083A3 - Способ получени производных 5-нитроимидазола - Google Patents
Способ получени производных 5-нитроимидазолаInfo
- Publication number
- SU637083A3 SU637083A3 SU752127886A SU2127886A SU637083A3 SU 637083 A3 SU637083 A3 SU 637083A3 SU 752127886 A SU752127886 A SU 752127886A SU 2127886 A SU2127886 A SU 2127886A SU 637083 A3 SU637083 A3 SU 637083A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- nitroimidazole
- residue
- water
- evaporated
- yield
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 2
- 150000004958 5-nitroimidazoles Chemical class 0.000 title 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- -1 (Ethylsulfonyl) - ethyl Chemical group 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 159000000009 barium salts Chemical class 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 2
- 125000005999 2-bromoethyl group Chemical group 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- XLGUKWZVVYEDAY-UHFFFAOYSA-N 1-(2-bromoethyl)-2-ethyl-5-nitroimidazole Chemical compound CCC1=NC=C([N+]([O-])=O)N1CCBr XLGUKWZVVYEDAY-UHFFFAOYSA-N 0.000 description 1
- ROXLQGHOPINWFU-UHFFFAOYSA-N 1-(2-iodoethyl)-2-methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCI ROXLQGHOPINWFU-UHFFFAOYSA-N 0.000 description 1
- WZFUQSJFWNHZHM-UHFFFAOYSA-N 2-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperazin-1-yl]-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethanone Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)N1CCN(CC1)CC(=O)N1CC2=C(CC1)NN=N2 WZFUQSJFWNHZHM-UHFFFAOYSA-N 0.000 description 1
- URTDCCYNLCMABU-UHFFFAOYSA-L C(C)S(=O)[O-].[Ca+2].C(C)S(=O)[O-] Chemical compound C(C)S(=O)[O-].[Ca+2].C(C)S(=O)[O-] URTDCCYNLCMABU-UHFFFAOYSA-L 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- UWIVVFQECQYHOB-UHFFFAOYSA-M sodium;ethanesulfinate Chemical compound [Na+].CCS([O-])=O UWIVVFQECQYHOB-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
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
- C07D233/66—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
- C07D233/92—Nitro radicals attached in position 4 or 5
- C07D233/94—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to other ring members
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH545974A CH605811A5 (enrdf_load_stackoverflow) | 1974-04-19 | 1974-04-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU637083A3 true SU637083A3 (ru) | 1978-12-05 |
Family
ID=4293954
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU752127886A SU637083A3 (ru) | 1974-04-19 | 1975-04-18 | Способ получени производных 5-нитроимидазола |
| SU762409560A SU671727A3 (ru) | 1974-04-19 | 1976-10-14 | Способ получени производных 5-нитроимидазола |
| SU762426144A SU659091A3 (ru) | 1974-04-19 | 1976-12-07 | Способ получени производных 5-нитроимидазола |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU762409560A SU671727A3 (ru) | 1974-04-19 | 1976-10-14 | Способ получени производных 5-нитроимидазола |
| SU762426144A SU659091A3 (ru) | 1974-04-19 | 1976-12-07 | Способ получени производных 5-нитроимидазола |
Country Status (20)
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2324682C2 (ru) * | 2002-10-15 | 2008-05-20 | Оцука Фармасьютикал Ко., Лтд. | Производное 1-замещенного 4-нитроимидазола и способ его получения |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS54119459A (en) * | 1978-03-08 | 1979-09-17 | Koba Tsuneyoshi | Antirheumatic |
| FR2647447B1 (fr) * | 1989-05-23 | 1991-08-23 | Rhone Poulenc Sante | Procede de preparation du (chloro-2 ethyl)-1 methyl-2 nitro-5 imidazole |
| WO2014030142A2 (en) * | 2012-08-24 | 2014-02-27 | Auckland Uniservices Limited | Nitroimidazole compounds and their use in cancer therapy |
-
1974
- 1974-04-19 CH CH545974A patent/CH605811A5/xx not_active IP Right Cessation
-
1975
- 1975-01-01 AR AR258173A patent/AR208080A1/es active
- 1975-03-24 FI FI750867A patent/FI750867A7/fi not_active Application Discontinuation
- 1975-04-03 AT AT254975A patent/AT351523B/de not_active IP Right Cessation
- 1975-04-07 DE DE19752515110 patent/DE2515110A1/de not_active Withdrawn
- 1975-04-08 ES ES436422A patent/ES436422A1/es not_active Expired
- 1975-04-09 GB GB1451875A patent/GB1446301A/en not_active Expired
- 1975-04-09 IE IE800/75A patent/IE40915B1/xx unknown
- 1975-04-09 ZA ZA00752255A patent/ZA752255B/xx unknown
- 1975-04-11 IL IL47071A patent/IL47071A0/xx unknown
- 1975-04-15 NO NO751323A patent/NO143626C/no unknown
- 1975-04-16 BE BE155460A patent/BE828001A/xx unknown
- 1975-04-18 SE SE7504507A patent/SE7504507L/xx unknown
- 1975-04-18 CA CA225,425A patent/CA1033747A/en not_active Expired
- 1975-04-18 DK DK166475A patent/DK166475A/da not_active Application Discontinuation
- 1975-04-18 JP JP4735575A patent/JPS5314073B2/ja not_active Expired
- 1975-04-18 SU SU752127886A patent/SU637083A3/ru active
- 1975-04-18 FR FR7512225A patent/FR2268017B1/fr not_active Expired
- 1975-04-18 HU HU75CE1042A patent/HU173570B/hu unknown
- 1975-04-21 NL NL7504718A patent/NL7504718A/xx not_active Application Discontinuation
-
1976
- 1976-10-14 SU SU762409560A patent/SU671727A3/ru active
- 1976-12-07 SU SU762426144A patent/SU659091A3/ru active
-
1977
- 1977-10-14 JP JP52123404A patent/JPS5935400B2/ja not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2324682C2 (ru) * | 2002-10-15 | 2008-05-20 | Оцука Фармасьютикал Ко., Лтд. | Производное 1-замещенного 4-нитроимидазола и способ его получения |
Also Published As
| Publication number | Publication date |
|---|---|
| ZA752255B (en) | 1976-02-25 |
| NL7504718A (nl) | 1975-10-21 |
| NO143626B (no) | 1980-12-08 |
| SU659091A3 (ru) | 1979-04-25 |
| CA1033747A (en) | 1978-06-27 |
| JPS5935400B2 (ja) | 1984-08-28 |
| SE7504507L (sv) | 1975-10-20 |
| DK166475A (da) | 1975-10-20 |
| JPS50148358A (enrdf_load_stackoverflow) | 1975-11-27 |
| SU671727A3 (ru) | 1979-06-30 |
| BE828001A (fr) | 1975-08-18 |
| ATA254975A (de) | 1979-01-15 |
| NO143626C (no) | 1981-03-18 |
| FR2268017B1 (enrdf_load_stackoverflow) | 1979-03-16 |
| ES436422A1 (es) | 1977-04-01 |
| IL47071A0 (en) | 1975-06-25 |
| GB1446301A (en) | 1976-08-18 |
| NO751323L (enrdf_load_stackoverflow) | 1975-10-21 |
| IE40915L (en) | 1975-10-19 |
| AR208080A1 (es) | 1976-11-30 |
| JPS5387355A (en) | 1978-08-01 |
| FI750867A7 (enrdf_load_stackoverflow) | 1975-10-20 |
| CH605811A5 (enrdf_load_stackoverflow) | 1978-10-13 |
| HU173570B (hu) | 1979-06-28 |
| IE40915B1 (en) | 1979-09-12 |
| FR2268017A1 (enrdf_load_stackoverflow) | 1975-11-14 |
| AT351523B (de) | 1979-07-25 |
| JPS5314073B2 (enrdf_load_stackoverflow) | 1978-05-15 |
| DE2515110A1 (de) | 1975-10-23 |
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