NO122374B - - Google Patents
Download PDFInfo
- Publication number
- NO122374B NO122374B NO165769A NO165769A NO122374B NO 122374 B NO122374 B NO 122374B NO 165769 A NO165769 A NO 165769A NO 165769 A NO165769 A NO 165769A NO 122374 B NO122374 B NO 122374B
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- nitroimidazole
- approx
- compound
- general formula
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 14
- 238000002360 preparation method Methods 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- 241000271566 Aves Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 244000144977 poultry Species 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- MFFPOGNCQPYWEX-UHFFFAOYSA-N 2-(5-nitro-1H-imidazol-2-yl)benzoic acid Chemical compound OC(=O)C1=CC=CC=C1C1=NC=C([N+]([O-])=O)N1 MFFPOGNCQPYWEX-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 241000286209 Phasianidae Species 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 235000005822 corn Nutrition 0.000 description 3
- 239000003085 diluting agent Substances 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000003651 drinking water Substances 0.000 description 3
- 235000020188 drinking water Nutrition 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- -1 nitroimidazo-isoindoles Chemical class 0.000 description 3
- HJKLEAOXCZIMPI-UHFFFAOYSA-N 2,2-diethoxyethanamine Chemical compound CCOC(CN)OCC HJKLEAOXCZIMPI-UHFFFAOYSA-N 0.000 description 2
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 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
- 241000224526 Trichomonas Species 0.000 description 2
- 208000005448 Trichomonas Infections Diseases 0.000 description 2
- 241000224527 Trichomonas vaginalis Species 0.000 description 2
- 206010044620 Trichomoniasis Diseases 0.000 description 2
- 206010046914 Vaginal infection Diseases 0.000 description 2
- SHAXJRGMYFOSSQ-UHFFFAOYSA-N [2-(5-nitro-1H-imidazol-2-yl)phenyl]methanol Chemical compound OCC1=C(C=CC=C1)C=1NC=C(N1)[N+](=O)[O-] SHAXJRGMYFOSSQ-UHFFFAOYSA-N 0.000 description 2
- 206010000496 acne Diseases 0.000 description 2
- 235000019270 ammonium chloride Nutrition 0.000 description 2
- 230000001572 anti-trichomonad Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 239000002026 chloroform extract Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- VDFHYUDENNTZKS-UHFFFAOYSA-N ethyl 2-cyanobenzenecarboximidate;hydrochloride Chemical compound Cl.CCOC(=N)C1=CC=CC=C1C#N VDFHYUDENNTZKS-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000012467 final product Substances 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- HIFJUMGIHIZEPX-UHFFFAOYSA-N sulfuric acid;sulfur trioxide Chemical compound O=S(=O)=O.OS(O)(=O)=O HIFJUMGIHIZEPX-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- VHBHOFCCXQFQCL-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)benzoic acid;hydrochloride Chemical compound Cl.OC(=O)C1=CC=CC=C1C1=NC=CN1 VHBHOFCCXQFQCL-UHFFFAOYSA-N 0.000 description 1
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000207199 Citrus Species 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000948220 Histomonas meleagridis Species 0.000 description 1
- 240000004658 Medicago sativa Species 0.000 description 1
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 1
- 208000027954 Poultry disease Diseases 0.000 description 1
- 208000010362 Protozoan Infections Diseases 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 240000006394 Sorghum bicolor Species 0.000 description 1
- 235000019764 Soybean Meal Nutrition 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 235000021307 Triticum Nutrition 0.000 description 1
- 201000008100 Vaginitis Diseases 0.000 description 1
- 239000005862 Whey Substances 0.000 description 1
- 102000007544 Whey Proteins Human genes 0.000 description 1
- 108010046377 Whey Proteins Proteins 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000842 anti-protozoal effect Effects 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 235000015155 buttermilk Nutrition 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- UHZZMRAGKVHANO-UHFFFAOYSA-M chlormequat chloride Chemical compound [Cl-].C[N+](C)(C)CCCl UHZZMRAGKVHANO-UHFFFAOYSA-M 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 235000019688 fish Nutrition 0.000 description 1
- 244000144992 flock Species 0.000 description 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 230000000802 nitrating effect Effects 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 235000016709 nutrition Nutrition 0.000 description 1
- 230000035764 nutrition Effects 0.000 description 1
- 238000010422 painting Methods 0.000 description 1
- 230000000590 parasiticidal effect Effects 0.000 description 1
- 239000002297 parasiticide Substances 0.000 description 1
- XQZYPMVTSDWCCE-UHFFFAOYSA-N phthalonitrile Chemical compound N#CC1=CC=CC=C1C#N XQZYPMVTSDWCCE-UHFFFAOYSA-N 0.000 description 1
- 229920006391 phthalonitrile polymer Polymers 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 244000000040 protozoan parasite Species 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000021055 solid food Nutrition 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000004455 soybean meal Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 239000005418 vegetable material Substances 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 235000015099 wheat brans Nutrition 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO165769A NO122374B (enrdf_load_stackoverflow) | 1964-03-10 | 1969-04-22 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US350639A US3399211A (en) | 1964-03-10 | 1964-03-10 | Production of 2-aryl-4(5)-nitroimidazoles |
| NO157118A NO121445B (enrdf_load_stackoverflow) | 1964-03-10 | 1965-03-09 | |
| US72464968A | 1968-02-02 | 1968-02-02 | |
| NO165769A NO122374B (enrdf_load_stackoverflow) | 1964-03-10 | 1969-04-22 | |
| US84374969A | 1969-07-22 | 1969-07-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO122374B true NO122374B (enrdf_load_stackoverflow) | 1971-06-21 |
Family
ID=27532545
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO165769A NO122374B (enrdf_load_stackoverflow) | 1964-03-10 | 1969-04-22 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO122374B (enrdf_load_stackoverflow) |
-
1969
- 1969-04-22 NO NO165769A patent/NO122374B/no unknown
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3461206A (en) | Compositions containing a sulfanilamide and a 2,4-diamino-5-(2',4',5'-trisubstitutedbenzyl)pyrimidine | |
| EP0015124B1 (en) | Parasiticidal heterocyclic ether derivatives, processes for the manufacture thereof and compositions thereof | |
| US4010176A (en) | Isoxazole substituted nitroimidazoles | |
| US3487087A (en) | Nitration of imidazoles | |
| EP0116639A1 (en) | Acyl guanidines | |
| US3652579A (en) | 1-methyl-2-substituted 5-nitroimidazoles | |
| SU1477247A3 (ru) | Способ получени триазолилхинолиновых производных или их солей присоединени кислот | |
| FI86188C (fi) | Foerfarande foer framstaellning av ett polycykliskt eterantibiotikum som kan anvaendas saosom laekemedel. | |
| US3020277A (en) | 1-(2-n-propyl-4-amino-5-pyrimidyl-methyl)-2(or 4)-methyl pyridinium salts | |
| NO122374B (enrdf_load_stackoverflow) | ||
| US4173631A (en) | 7-Methyl-8-methylamino-10-(1'-D-ribityl)isoalloxazine | |
| US3666860A (en) | Substituted nitroimidazolylthiadiazoles and oxadiazoles as antiprotozoal agents | |
| DE1670389A1 (de) | Neue quaternaere 5-Ammonium-methyl-4-amino-pyrimidinsalzverbindungen | |
| US3842174A (en) | Substituted nitroimidazolylthiadiazoles and oxadiazoles as antiprotozoal agents | |
| US3634446A (en) | 1-methyl-2-isopropyl-5-nitroimidazole and water soluble salts thereof | |
| US4356264A (en) | Zinc-containing antibiotic agents | |
| US3676439A (en) | 5,6-dihydro-8,8-dimethyl-3-nitro-8h imidazo(2-1-c) (1,4)oxazine | |
| NO123461B (enrdf_load_stackoverflow) | ||
| US4079069A (en) | 5-Deazariboflavin and its derivatives | |
| DE1518045A1 (de) | 2-Alkoxy-4-subst.-Benzylverbindungen und Verfahren zu ihrer Herstellung | |
| US4091094A (en) | 9-Azariboflavin and pharmaceutical composition containing same | |
| US4154835A (en) | Anthelmintic imidazo [1,2-a] pyridines | |
| US3859443A (en) | Composition and methods of treatment employing acrylanilides as anticoccidial agents | |
| US3637702A (en) | 1-(hydroxyalkyl)-2-morpholinomethyl-5-nitroimidazoles | |
| US3654299A (en) | Nitroimidazolyl antimicrobial agents |