IL33278A - 2-nitroimidazoles with antibacterial activity and their preparation - Google Patents
2-nitroimidazoles with antibacterial activity and their preparationInfo
- Publication number
- IL33278A IL33278A IL33278A IL3327869A IL33278A IL 33278 A IL33278 A IL 33278A IL 33278 A IL33278 A IL 33278A IL 3327869 A IL3327869 A IL 3327869A IL 33278 A IL33278 A IL 33278A
- Authority
- IL
- Israel
- Prior art keywords
- iimmiiddaazzoollee
- ccoommppoouunndd
- aass
- yield
- solution
- Prior art date
Links
- 230000000844 anti-bacterial effect Effects 0.000 title description 3
- 238000002360 preparation method Methods 0.000 title description 3
- 150000004959 2-nitroimidazoles Chemical class 0.000 title 1
- 101150018711 AASS gene Proteins 0.000 claims 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 9
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 8
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229910052708 sodium Inorganic materials 0.000 description 7
- 239000011734 sodium Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 235000010288 sodium nitrite Nutrition 0.000 description 4
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- -1 alkali metal nitrite Chemical class 0.000 description 3
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000001988 toxicity Effects 0.000 description 2
- 231100000419 toxicity Toxicity 0.000 description 2
- JDIIGWSSTNUWGK-UHFFFAOYSA-N 1h-imidazol-3-ium;chloride Chemical compound [Cl-].[NH2+]1C=CN=C1 JDIIGWSSTNUWGK-UHFFFAOYSA-N 0.000 description 1
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 150000001241 acetals Chemical class 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 239000012675 alcoholic extract Substances 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000003716 antitrichomonal agent Substances 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 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
- C07D233/88—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
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Rectifiers (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT2376668 | 1968-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL33278A0 IL33278A0 (en) | 1969-12-31 |
| IL33278A true IL33278A (en) | 1973-02-28 |
Family
ID=11209793
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL33278A IL33278A (en) | 1968-11-15 | 1969-10-29 | 2-nitroimidazoles with antibacterial activity and their preparation |
Country Status (15)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3987053A (en) * | 1971-07-30 | 1976-10-19 | Gruppo Lepetit S.P.A. | 2-nitroimidazol derivatives |
| 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 |
| GB1480192A (en) * | 1975-01-15 | 1977-07-20 | Lepetit Spa | 1-methyl-2-nitro-imidazole-5-methanol derivatives |
-
1969
- 1969-10-28 NL NL696916247A patent/NL143227B/xx not_active IP Right Cessation
- 1969-10-29 IL IL33278A patent/IL33278A/en unknown
- 1969-11-07 DK DK589269AA patent/DK135770B/da not_active IP Right Cessation
- 1969-11-11 BR BR214070/69A patent/BR6914070D0/pt unknown
- 1969-11-13 LU LU59815D patent/LU59815A1/xx unknown
- 1969-11-13 SE SE6915607A patent/SE370699B/xx unknown
- 1969-11-13 GB GB1229170D patent/GB1229170A/en not_active Expired
- 1969-11-14 NO NO4526/69A patent/NO124876B/no unknown
- 1969-11-14 YU YU2859/69A patent/YU33271B/xx unknown
- 1969-11-14 AT AT1068769A patent/AT287703B/de not_active IP Right Cessation
- 1969-11-14 CH CH1697769A patent/CH510672A/fr not_active IP Right Cessation
- 1969-11-14 BE BE741692D patent/BE741692A/xx unknown
- 1969-11-14 FI FI693288A patent/FI51180C/fi active
- 1969-11-14 FR FR696939233A patent/FR2023418B1/fr not_active Expired
- 1969-11-15 ES ES373569A patent/ES373569A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL143227B (nl) | 1974-09-16 |
| GB1229170A (enrdf_load_stackoverflow) | 1971-04-21 |
| ES373569A1 (es) | 1972-02-01 |
| IL33278A0 (en) | 1969-12-31 |
| FI51180B (enrdf_load_stackoverflow) | 1976-08-02 |
| AT287703B (de) | 1971-02-10 |
| FR2023418B1 (enrdf_load_stackoverflow) | 1973-01-12 |
| DK135770B (da) | 1977-06-20 |
| DK135770C (enrdf_load_stackoverflow) | 1977-11-21 |
| BE741692A (enrdf_load_stackoverflow) | 1970-04-16 |
| FR2023418A1 (enrdf_load_stackoverflow) | 1970-08-21 |
| NO124876B (enrdf_load_stackoverflow) | 1972-06-19 |
| NL6916247A (enrdf_load_stackoverflow) | 1970-05-20 |
| FI51180C (fi) | 1976-11-10 |
| SE370699B (enrdf_load_stackoverflow) | 1974-10-28 |
| DE1956986A1 (de) | 1970-05-27 |
| BR6914070D0 (pt) | 1973-02-13 |
| YU285969A (en) | 1976-03-31 |
| LU59815A1 (enrdf_load_stackoverflow) | 1970-01-13 |
| CH510672A (fr) | 1971-07-31 |
| YU33271B (en) | 1976-08-31 |
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