IL25677A - History of imidazole and process for their production - Google Patents
History of imidazole and process for their productionInfo
- Publication number
- IL25677A IL25677A IL25677A IL2567766A IL25677A IL 25677 A IL25677 A IL 25677A IL 25677 A IL25677 A IL 25677A IL 2567766 A IL2567766 A IL 2567766A IL 25677 A IL25677 A IL 25677A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- nitroimidazole
- preparation
- compounds
- hydroxypropyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 12
- 150000002460 imidazoles Chemical class 0.000 title description 2
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 238000002360 preparation method Methods 0.000 claims description 17
- 150000001875 compounds Chemical class 0.000 claims description 16
- 239000000203 mixture Substances 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 6
- 150000002367 halogens Chemical class 0.000 claims description 6
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 230000020477 pH reduction Effects 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 230000000802 nitrating effect Effects 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 239000000047 product Substances 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- 238000003756 stirring Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 229920002261 Corn starch Polymers 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000008120 corn starch Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 5
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 5
- 239000011630 iodine Substances 0.000 description 5
- 229910052740 iodine Inorganic materials 0.000 description 5
- 239000008101 lactose Substances 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- NLXRQOREXATYEE-UHFFFAOYSA-N 2-methyl-5-nitro-1-(oxiran-2-ylmethyl)imidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CC1OC1 NLXRQOREXATYEE-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 240000008042 Zea mays Species 0.000 description 4
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 235000005822 corn Nutrition 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- 238000006396 nitration reaction Methods 0.000 description 4
- 239000000829 suppository Substances 0.000 description 4
- IPWKIXLWTCNBKN-UHFFFAOYSA-N Madelen Chemical compound CC1=NC=C([N+]([O-])=O)N1CC(O)CCl IPWKIXLWTCNBKN-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- -1 i.e. Inorganic materials 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- ZRFRHNXTIRSYSG-UHFFFAOYSA-N 1-chloro-3-(4-iodo-2-methyl-5-nitroimidazol-1-yl)propan-2-ol Chemical compound CC1=NC(I)=C([N+]([O-])=O)N1CC(O)CCl ZRFRHNXTIRSYSG-UHFFFAOYSA-N 0.000 description 2
- XMWPTVMTXKJONE-UHFFFAOYSA-N 4,5-diiodo-1h-imidazole Chemical compound IC=1N=CNC=1I XMWPTVMTXKJONE-UHFFFAOYSA-N 0.000 description 2
- 150000004958 5-nitroimidazoles Chemical class 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 2
- 239000008116 calcium stearate Substances 0.000 description 2
- 235000013539 calcium stearate Nutrition 0.000 description 2
- 239000007963 capsule composition Substances 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 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
- 238000009472 formulation Methods 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical group [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000000967 suction filtration Methods 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000007916 tablet composition Substances 0.000 description 2
- VUKSFMNOZJMMPR-UHFFFAOYSA-N 1,2-diiodoimidazole Chemical compound IC1=NC=CN1I VUKSFMNOZJMMPR-UHFFFAOYSA-N 0.000 description 1
- KMSPJBJNMWAORS-UHFFFAOYSA-N 1-chloro-3-(2-iodo-4-nitroimidazol-1-yl)propan-2-ol Chemical compound ClCC(O)CN1C=C([N+]([O-])=O)N=C1I KMSPJBJNMWAORS-UHFFFAOYSA-N 0.000 description 1
- VAGCYSKTWCDULE-UHFFFAOYSA-N 1-chloro-3-(5-iodo-2-methyl-4-nitroimidazol-1-yl)propan-2-ol Chemical compound CC1=NC([N+]([O-])=O)=C(I)N1CC(O)CCl VAGCYSKTWCDULE-UHFFFAOYSA-N 0.000 description 1
- FFYTTYVSDVWNMY-UHFFFAOYSA-N 2-Methyl-5-nitroimidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1 FFYTTYVSDVWNMY-UHFFFAOYSA-N 0.000 description 1
- GTPNXFKONRIHRW-UHFFFAOYSA-N 2-iodo-1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=C(I)C(C)=C1 GTPNXFKONRIHRW-UHFFFAOYSA-N 0.000 description 1
- SLXKMUNIPNNJGS-UHFFFAOYSA-N 4-iodo-2-methyl-5-nitro-1-(oxiran-2-ylmethyl)imidazole Chemical compound CC1=NC(I)=C([N+]([O-])=O)N1CC1OC1 SLXKMUNIPNNJGS-UHFFFAOYSA-N 0.000 description 1
- 150000004960 4-nitroimidazoles Chemical class 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000000659 freezing mixture Substances 0.000 description 1
- 239000000295 fuel oil Substances 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000010899 nucleation Methods 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 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
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000000080 wetting agent 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
-
- 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
- C07D233/68—Halogen atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US45721265A | 1965-05-19 | 1965-05-19 | |
| US76890868A | 1968-10-18 | 1968-10-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IL25677A true IL25677A (en) | 1970-05-21 |
Family
ID=27038516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL25677A IL25677A (en) | 1965-05-19 | 1966-05-01 | History of imidazole and process for their production |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US3435049A (en, 2012) |
| BE (1) | BE681144A (en, 2012) |
| BR (1) | BR6679399D0 (en, 2012) |
| CH (1) | CH469716A (en, 2012) |
| DE (1) | DE1695139B2 (en, 2012) |
| DK (1) | DK114629B (en, 2012) |
| FR (1) | FR5448M (en, 2012) |
| GB (3) | GB1099787A (en, 2012) |
| IL (1) | IL25677A (en, 2012) |
| NL (1) | NL148889B (en, 2012) |
| SE (1) | SE337030B (en, 2012) |
Families Citing this family (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3700685A (en) * | 1970-05-15 | 1972-10-24 | Merck & Co Inc | Nitroimidazole derivatives |
| US4218449A (en) * | 1978-08-21 | 1980-08-19 | John R. A. Simoons | Treatment of rheumatoid arthritis and related diseases |
| JPS5692887A (en) * | 1979-12-05 | 1981-07-27 | Sumitomo Chem Co Ltd | N-substituted imidazole derivative |
| FR2509302A1 (fr) * | 1981-03-04 | 1983-01-14 | Vyzk Ustav Zuslechtovaci | Composes d'ammonium quaternaire, procede pour leur fabrication et utilisation de ces produits dans les apprets de finissage des tissus |
| DE3218130A1 (de) * | 1982-05-14 | 1983-11-17 | Basf Ag, 6700 Ludwigshafen | Azolylmethyloxirane, verfahren zu ihrer herstellung und diese enthaltende fungizide |
| CH669494GA3 (en, 2012) * | 1984-11-05 | 1989-03-31 | ||
| ZA858242B (en) * | 1985-01-21 | 1986-08-27 | Ciba Geigy Ag | Cationic reaction products formed from 1-aminoalkyl-imidazole compounds and epihalohydrins |
| CH672219B5 (en, 2012) * | 1985-01-25 | 1990-05-15 | Ciba Geigy Ag | |
| FR2624736B1 (fr) * | 1987-12-16 | 1991-03-22 | Dietlin Francois | Nouvelles compositions pharmaceutiques dispersibles dans l'eau a base d'ornidazole |
| DE3825586A1 (de) * | 1988-07-28 | 1990-02-01 | Basf Ag | Substituierte imidazolylmethyloxirane und substituierte imidazolylpropene, ihre herstellung und sie enthaltende fungizide |
| FR2647448B1 (fr) * | 1989-05-23 | 1991-08-23 | Rhone Poulenc Sante | Procede de preparation du (chloro-3 hydroxy-2 propyl)-1 methyl-2 nitro-5 imidazole |
| EP1553088A4 (en) * | 2002-10-15 | 2011-03-02 | Otsuka Pharma Co Ltd | 1-SUBSTITUTED 4-NITROIMIDAZOLE COMPOUND AND PROCESS FOR PRODUCING THE SAME |
| CN100338039C (zh) * | 2004-11-29 | 2007-09-19 | 南京圣和药业有限公司 | 奥硝唑光学对映体的制备及纯化方法 |
| CN1314396C (zh) * | 2005-04-28 | 2007-05-09 | 南京圣和药业有限公司 | 左旋奥硝唑在制备抗厌氧菌感染药物的应用 |
| CN1332662C (zh) * | 2005-04-29 | 2007-08-22 | 南京圣和药业有限公司 | 左旋奥硝唑的静脉给药制剂及其制备方法 |
| CN1305469C (zh) * | 2005-07-08 | 2007-03-21 | 南京圣和药业有限公司 | 左旋奥硝唑在制备抗寄生虫感染的药物中的应用 |
| CN100368402C (zh) * | 2005-11-16 | 2008-02-13 | 沈阳中海生物技术开发有限公司 | 奥硝唑光学对映体的制备方法 |
| US9237750B2 (en) * | 2012-07-04 | 2016-01-19 | Ramot At Tel-Aviv University Ltd. | Ornidazole and related compounds for use as herbicides |
| CN103073501B (zh) * | 2012-12-07 | 2014-10-15 | 西安万隆制药股份有限公司 | 一种奥硝唑化合物 |
| CN105585532B (zh) * | 2014-10-24 | 2018-05-01 | 山东齐都药业有限公司 | 左奥硝唑反应液的后处理方法 |
| CN105061323A (zh) * | 2015-07-31 | 2015-11-18 | 珠海亿邦制药股份有限公司 | 一种奥硝唑化合物的精制方法 |
| CN107235911A (zh) * | 2016-03-28 | 2017-10-10 | 陕西合成药业股份有限公司 | 一种2-甲基-4-硝基咪唑衍生物及其制备方法和药用组合物的用途 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3275649A (en) * | 1966-09-27 | Process for the preparation of | ||
| US2061377A (en) * | 1934-06-25 | 1936-11-17 | Shell Dev | Conversion of polyhalogenated alcohols |
| US2116439A (en) * | 1936-04-21 | 1938-05-03 | Du Pont | Cyclic oxides and their preparation |
| DE1011618B (de) * | 1954-12-06 | 1957-07-04 | Bayer Ag | Verfahren zur Herstellung basischer Diepoxydharze |
| US3043819A (en) * | 1959-09-15 | 1962-07-10 | Union Carbide Corp | 2-(pyrazol)ethyl acrylates, process for their production, and polymerization products thereof |
| DE1445963A1 (de) * | 1962-04-06 | 1969-12-04 | Klosa Dipl Chem Dr Josef | Verfahren zur Herstellung eines neuen Imidazolderivates |
| FR1379915A (fr) * | 1963-12-17 | 1964-11-27 | Rhone Poulenc Sa | Procédé de préparation de dérivés de l'imidazole |
-
1965
- 1965-05-19 US US457212A patent/US3435049A/en not_active Expired - Lifetime
-
1966
- 1966-04-27 CH CH610766A patent/CH469716A/de unknown
- 1966-04-29 DE DE1966H0059257 patent/DE1695139B2/de active Granted
- 1966-05-01 IL IL25677A patent/IL25677A/en unknown
- 1966-05-11 BR BR179399/66A patent/BR6679399D0/pt unknown
- 1966-05-13 GB GB21427/66A patent/GB1099787A/en not_active Expired
- 1966-05-13 FR FR61416A patent/FR5448M/fr not_active Expired
- 1966-05-13 GB GB32760/67A patent/GB1099788A/en not_active Expired
- 1966-05-13 GB GB32761/67A patent/GB1099789A/en not_active Expired
- 1966-05-17 BE BE681144D patent/BE681144A/xx not_active IP Right Cessation
- 1966-05-18 DK DK254466AA patent/DK114629B/da unknown
- 1966-05-18 NL NL666606853A patent/NL148889B/xx not_active IP Right Cessation
- 1966-05-18 SE SE06943/66A patent/SE337030B/xx unknown
-
1968
- 1968-10-18 US US768908A patent/US3493582A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB1099788A (en) | 1968-01-17 |
| US3493582A (en) | 1970-02-03 |
| DE1695139B2 (de) | 1976-11-04 |
| SE337030B (en, 2012) | 1971-07-26 |
| GB1099789A (en) | 1968-01-17 |
| US3435049A (en) | 1969-03-25 |
| DK114629B (da) | 1969-07-21 |
| FR5448M (en, 2012) | 1967-10-09 |
| CH469716A (de) | 1969-03-15 |
| BE681144A (en, 2012) | 1966-11-17 |
| NL6606853A (en, 2012) | 1966-11-21 |
| BR6679399D0 (pt) | 1973-10-23 |
| DE1695139A1 (de) | 1970-12-17 |
| NL148889B (nl) | 1976-03-15 |
| GB1099787A (en) | 1968-01-17 |
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