DE1920635C3 - 2-(l-MethyI-5-nitro-2-imidazolyl)benzimidazole - Google Patents
2-(l-MethyI-5-nitro-2-imidazolyl)benzimidazoleInfo
- Publication number
- DE1920635C3 DE1920635C3 DE1920635A DE1920635A DE1920635C3 DE 1920635 C3 DE1920635 C3 DE 1920635C3 DE 1920635 A DE1920635 A DE 1920635A DE 1920635 A DE1920635 A DE 1920635A DE 1920635 C3 DE1920635 C3 DE 1920635C3
- Authority
- DE
- Germany
- Prior art keywords
- nitro
- methyl
- imidazolyl
- benzimidazole
- melting point
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- QBLKKIYJFMCHEA-UHFFFAOYSA-N 2-(1-methyl-5-nitroimidazol-2-yl)-1h-benzimidazole Chemical class C1=C([N+]([O-])=O)N(C)C(C=2NC3=CC=CC=C3N=2)=N1 QBLKKIYJFMCHEA-UHFFFAOYSA-N 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000002844 melting Methods 0.000 description 17
- 230000008018 melting Effects 0.000 description 17
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- -1 1-methyl-5-nitro-2-imidazolyl Chemical group 0.000 description 8
- 150000004985 diamines Chemical class 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 5
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 4
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 241000224527 Trichomonas vaginalis Species 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- CDCUIKNWTWKVLW-UHFFFAOYSA-N hydrazine;palladium Chemical compound [Pd].NN CDCUIKNWTWKVLW-UHFFFAOYSA-N 0.000 description 2
- UKWHYYKOEPRTIC-UHFFFAOYSA-N mercury(ii) oxide Chemical compound [Hg]=O UKWHYYKOEPRTIC-UHFFFAOYSA-N 0.000 description 2
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 2
- 229960000282 metronidazole Drugs 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000007800 oxidant agent Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 1
- NWESJZZPAJGHRZ-UHFFFAOYSA-N 1-chloro-4-methyl-2-nitrobenzene Chemical compound CC1=CC=C(Cl)C([N+]([O-])=O)=C1 NWESJZZPAJGHRZ-UHFFFAOYSA-N 0.000 description 1
- KPZWNYSWNWWBBW-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carboxylic acid Chemical compound CN1C(C(O)=O)=NC=C1[N+]([O-])=O KPZWNYSWNWWBBW-UHFFFAOYSA-N 0.000 description 1
- WXYPROOOTXZVOP-UHFFFAOYSA-N 2-(1-methyl-5-nitroimidazol-2-yl)-1-(2-pyrrolidin-1-ylethyl)benzimidazole Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC2=CC=CC=C2N1CCN1CCCC1 WXYPROOOTXZVOP-UHFFFAOYSA-N 0.000 description 1
- VUNFYZZNGWQFHN-UHFFFAOYSA-N 2-n-(2-morpholin-4-ylethyl)benzene-1,2-diamine Chemical compound NC1=CC=CC=C1NCCN1CCOCC1 VUNFYZZNGWQFHN-UHFFFAOYSA-N 0.000 description 1
- IIISXLQLWIFUIE-UHFFFAOYSA-N 2-n-(3-morpholin-4-ylpropyl)benzene-1,2-diamine Chemical compound NC1=CC=CC=C1NCCCN1CCOCC1 IIISXLQLWIFUIE-UHFFFAOYSA-N 0.000 description 1
- FPQSHGMAOKQNRO-UHFFFAOYSA-N 2-n-[3-(dibutylamino)propyl]benzene-1,2-diamine Chemical compound CCCCN(CCCC)CCCNC1=CC=CC=C1N FPQSHGMAOKQNRO-UHFFFAOYSA-N 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- XSZYBMMYQCYIPC-UHFFFAOYSA-N 4,5-dimethyl-1,2-phenylenediamine Chemical compound CC1=CC(N)=C(N)C=C1C XSZYBMMYQCYIPC-UHFFFAOYSA-N 0.000 description 1
- DGRGLKZMKWPMOH-UHFFFAOYSA-N 4-methylbenzene-1,2-diamine Chemical compound CC1=CC=C(N)C(N)=C1 DGRGLKZMKWPMOH-UHFFFAOYSA-N 0.000 description 1
- RWDINDJBXPDZMF-UHFFFAOYSA-N 5,6-dimethyl-2-(1-methyl-5-nitroimidazol-2-yl)-1h-benzimidazole Chemical compound N1C=2C=C(C)C(C)=CC=2N=C1C1=NC=C([N+]([O-])=O)N1C RWDINDJBXPDZMF-UHFFFAOYSA-N 0.000 description 1
- MWWZWULIKKPADB-UHFFFAOYSA-N 6-methyl-2-(1-methyl-5-nitroimidazol-2-yl)-1h-benzimidazole Chemical compound N1C2=CC(C)=CC=C2N=C1C1=NC=C([N+]([O-])=O)N1C MWWZWULIKKPADB-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241000243251 Hydra Species 0.000 description 1
- 102000006835 Lamins Human genes 0.000 description 1
- 108010047294 Lamins Proteins 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 241000224526 Trichomonas Species 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 230000003113 alkalizing effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 125000003943 azolyl group Chemical group 0.000 description 1
- 150000001556 benzimidazoles Chemical class 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 1
- 210000005053 lamin Anatomy 0.000 description 1
- ACKFDYCQCBEDNU-UHFFFAOYSA-J lead(2+);tetraacetate Chemical compound [Pb+2].CC([O-])=O.CC([O-])=O.CC([O-])=O.CC([O-])=O ACKFDYCQCBEDNU-UHFFFAOYSA-J 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- RFLLBXFWLRXKST-UHFFFAOYSA-N n',n'-dibutyl-n-(2-nitrophenyl)propane-1,3-diamine Chemical compound CCCCN(CCCC)CCCNC1=CC=CC=C1[N+]([O-])=O RFLLBXFWLRXKST-UHFFFAOYSA-N 0.000 description 1
- KYCGURZGBKFEQB-UHFFFAOYSA-N n',n'-dibutylpropane-1,3-diamine Chemical compound CCCCN(CCCC)CCCN KYCGURZGBKFEQB-UHFFFAOYSA-N 0.000 description 1
- DGAAQTGQRDJKLO-UHFFFAOYSA-N n',n'-dimethyl-n-(4-methyl-2-nitrophenyl)ethane-1,2-diamine Chemical compound CN(C)CCNC1=CC=C(C)C=C1[N+]([O-])=O DGAAQTGQRDJKLO-UHFFFAOYSA-N 0.000 description 1
- KFBOUJZFFJDYTA-UHFFFAOYSA-N n-methyl-2-nitroaniline Chemical compound CNC1=CC=CC=C1[N+]([O-])=O KFBOUJZFFJDYTA-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07D233/95—Nitro radicals attached in position 4 or 5 with hydrocarbon radicals, substituted by nitrogen atoms, attached to other ring members
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/325—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups reduction by other means than indicated in C07C209/34 or C07C209/36
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/30—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds
- C07C209/32—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups
- C07C209/36—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of nitrogen-to-oxygen or nitrogen-to-nitrogen bonds by reduction of nitro groups by reduction of nitro groups bound to carbon atoms of six-membered aromatic rings in presence of hydrogen-containing gases and a catalyst
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1920635A DE1920635C3 (de) | 1969-04-19 | 1969-04-19 | 2-(l-MethyI-5-nitro-2-imidazolyl)benzimidazole |
| CS2059A CS167896B2 (enrdf_load_stackoverflow) | 1969-04-19 | 1970-03-27 | |
| CH491970A CH546774A (de) | 1969-04-19 | 1970-04-02 | Verfahren zur herstellung von 2-(5-nitro-2-imidazolyl)benzimidazolen. |
| CH1820172A CH546768A (de) | 1969-04-19 | 1970-04-02 | Verfahren zur herstellung von 2-(5-nitro-2-imidazolyl)benzimidazolen. |
| ES70378368A ES378368A1 (es) | 1969-04-19 | 1970-04-08 | Procedimiento para la preparacion de 2 - (5-nitro-2-imida- zolil) - ben-cimidazoles. |
| DK188570AA DK137758B (da) | 1969-04-19 | 1970-04-15 | Analogifremgangsmåde til fremstilling af 2-(5-nitro-2-imidazolyl)-benzimidazoler eller salte deraf. |
| FI701070A FI52861C (fi) | 1969-04-19 | 1970-04-17 | Menetelmä antimikrobisesti vaikuttavien 2-(5-nitro-2-imidatsolyyli)-be ntsimidatsolien valmistamiseksi. |
| BE749102D BE749102A (fr) | 1969-04-19 | 1970-04-17 | 2-(5-nitro-2-imidazolyl)-benzimidazoles et leur procede de preparation |
| NO01455/70A NO126624B (enrdf_load_stackoverflow) | 1969-04-19 | 1970-04-17 | |
| ZA702577A ZA702577B (en) | 1969-04-19 | 1970-04-17 | 2-(5-nitro-2-imidazolyl)-benzimidazoles |
| FR707013970A FR2042351B1 (enrdf_load_stackoverflow) | 1969-04-19 | 1970-04-17 | |
| AT351470A AT294075B (de) | 1969-04-19 | 1970-04-17 | Verfahren zur Herstellung von neuen 2-(5-Nitro-2-imidazolyl)-benzimidazolen und ihren Salzen |
| SE05326/70A SE364962B (enrdf_load_stackoverflow) | 1969-04-19 | 1970-04-17 | |
| JP45033734A JPS4914231B1 (enrdf_load_stackoverflow) | 1969-04-19 | 1970-04-20 | |
| GB1874370A GB1312056A (en) | 1969-04-19 | 1970-04-20 | 2-5,-nitro-2,-imidazolyl-benzimidazoles |
| NL7005703A NL7005703A (enrdf_load_stackoverflow) | 1969-04-19 | 1970-04-20 | |
| US05/287,852 US4053472A (en) | 1969-04-19 | 1972-09-11 | 2-(5-nitro-2-imidazolyl)-benzimidazoles |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1920635A DE1920635C3 (de) | 1969-04-19 | 1969-04-19 | 2-(l-MethyI-5-nitro-2-imidazolyl)benzimidazole |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1920635A1 DE1920635A1 (de) | 1970-10-29 |
| DE1920635B2 DE1920635B2 (de) | 1978-11-02 |
| DE1920635C3 true DE1920635C3 (de) | 1979-06-28 |
Family
ID=5732064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1920635A Expired DE1920635C3 (de) | 1969-04-19 | 1969-04-19 | 2-(l-MethyI-5-nitro-2-imidazolyl)benzimidazole |
Country Status (15)
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4053472A (en) * | 1969-04-19 | 1977-10-11 | Schering Aktiengesellschaft | 2-(5-nitro-2-imidazolyl)-benzimidazoles |
| IT1043840B (it) * | 1971-05-08 | 1980-02-29 | Poli Ind Chimica Spa | Pirimidine 2 5 disostituite e processo per la loro preparazione |
| US3996238A (en) * | 1972-02-08 | 1976-12-07 | Ciba-Geigy Corporation | 4- or 5-Nitroimidazoles and processes for their manufacture |
| BE795636A (fr) * | 1972-02-19 | 1973-08-20 | Schering Ag | Nitroimidazolylpyrimidines, et leur procede de preparation |
| PT78358B (en) * | 1983-04-07 | 1986-05-30 | Smith Kline French Lab | Chemical process |
| US5852011A (en) * | 1994-05-31 | 1998-12-22 | Mitsui Chemicals, Inc. | Benzimidazole derivatives |
| WO1996006831A1 (en) * | 1994-08-26 | 1996-03-07 | Auckland Division Cancer Society Of New Zealand Inc. | Novel dna-targeted alkylating agents |
-
1969
- 1969-04-19 DE DE1920635A patent/DE1920635C3/de not_active Expired
-
1970
- 1970-03-27 CS CS2059A patent/CS167896B2/cs unknown
- 1970-04-02 CH CH1820172A patent/CH546768A/xx not_active IP Right Cessation
- 1970-04-02 CH CH491970A patent/CH546774A/xx not_active IP Right Cessation
- 1970-04-08 ES ES70378368A patent/ES378368A1/es not_active Expired
- 1970-04-15 DK DK188570AA patent/DK137758B/da unknown
- 1970-04-17 ZA ZA702577A patent/ZA702577B/xx unknown
- 1970-04-17 NO NO01455/70A patent/NO126624B/no unknown
- 1970-04-17 BE BE749102D patent/BE749102A/xx unknown
- 1970-04-17 SE SE05326/70A patent/SE364962B/xx unknown
- 1970-04-17 AT AT351470A patent/AT294075B/de active
- 1970-04-17 FI FI701070A patent/FI52861C/fi active
- 1970-04-17 FR FR707013970A patent/FR2042351B1/fr not_active Expired
- 1970-04-20 NL NL7005703A patent/NL7005703A/xx not_active Application Discontinuation
- 1970-04-20 JP JP45033734A patent/JPS4914231B1/ja active Pending
- 1970-04-20 GB GB1874370A patent/GB1312056A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FI52861B (enrdf_load_stackoverflow) | 1977-08-31 |
| ES378368A1 (es) | 1972-06-16 |
| CH546768A (de) | 1974-03-15 |
| GB1312056A (en) | 1973-04-04 |
| CS167896B2 (enrdf_load_stackoverflow) | 1976-05-28 |
| ZA702577B (en) | 1971-01-27 |
| FR2042351B1 (enrdf_load_stackoverflow) | 1973-07-13 |
| SE364962B (enrdf_load_stackoverflow) | 1974-03-11 |
| DE1920635A1 (de) | 1970-10-29 |
| DK137758C (enrdf_load_stackoverflow) | 1978-10-09 |
| DE1920635B2 (de) | 1978-11-02 |
| JPS4914231B1 (enrdf_load_stackoverflow) | 1974-04-05 |
| NL7005703A (enrdf_load_stackoverflow) | 1970-10-21 |
| DK137758B (da) | 1978-05-01 |
| BE749102A (fr) | 1970-10-19 |
| FI52861C (fi) | 1977-12-12 |
| FR2042351A1 (enrdf_load_stackoverflow) | 1971-02-12 |
| AT294075B (de) | 1971-11-10 |
| NO126624B (enrdf_load_stackoverflow) | 1973-03-05 |
| CH546774A (de) | 1974-03-15 |
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