NO126624B - - Google Patents
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- Publication number
- NO126624B NO126624B NO01455/70A NO145570A NO126624B NO 126624 B NO126624 B NO 126624B NO 01455/70 A NO01455/70 A NO 01455/70A NO 145570 A NO145570 A NO 145570A NO 126624 B NO126624 B NO 126624B
- Authority
- NO
- Norway
- Prior art keywords
- nitro
- imidazolyl
- methyl
- carbon atoms
- benzimidazole
- Prior art date
Links
- 239000002253 acid Substances 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000004494 ethyl ester group Chemical group 0.000 claims description 10
- 150000004985 diamines Chemical class 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- ARMIPOZWLTZJQG-UHFFFAOYSA-N 2-(5-nitro-1H-imidazol-2-yl)-1H-benzimidazole Chemical class N1C([N+](=O)[O-])=CN=C1C1=NC2=CC=CC=C2N1 ARMIPOZWLTZJQG-UHFFFAOYSA-N 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims description 3
- 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 claims description 2
- XQOAOOXWHJJJNT-UHFFFAOYSA-N 2-n-(2-pyrrolidin-1-ylethyl)benzene-1,2-diamine Chemical compound NC1=CC=CC=C1NCCN1CCCC1 XQOAOOXWHJJJNT-UHFFFAOYSA-N 0.000 claims description 2
- IIISXLQLWIFUIE-UHFFFAOYSA-N 2-n-(3-morpholin-4-ylpropyl)benzene-1,2-diamine Chemical compound NC1=CC=CC=C1NCCCN1CCOCC1 IIISXLQLWIFUIE-UHFFFAOYSA-N 0.000 claims description 2
- NVKJOXRVEKMMHS-UHFFFAOYSA-N 5-nitro-1,2,4-triazol-3-one Chemical compound [O-][N+](=O)C1=NC(=O)N=N1 NVKJOXRVEKMMHS-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 125000004185 ester group Chemical group 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 238000002844 melting Methods 0.000 description 41
- 230000008018 melting Effects 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 8
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000012043 crude product Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 5
- 241000224527 Trichomonas vaginalis Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- 239000002244 precipitate Substances 0.000 description 5
- ORPVVAKYSXQCJI-UHFFFAOYSA-N 1-bromo-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Br ORPVVAKYSXQCJI-UHFFFAOYSA-N 0.000 description 4
- -1 2-hydroxyethyl-amino Chemical group 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 238000004821 distillation Methods 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- QBLKKIYJFMCHEA-UHFFFAOYSA-N 2-(1-methyl-5-nitroimidazol-2-yl)-1h-benzimidazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2NC3=CC=CC=C3N=2)=N1 QBLKKIYJFMCHEA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 229960000282 metronidazole Drugs 0.000 description 3
- 150000002825 nitriles Chemical class 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- 238000012746 preparative thin layer chromatography Methods 0.000 description 3
- YQKHOTXTHRUMHE-UHFFFAOYSA-N 1-(2-chloroethyl)-2-(1-methyl-5-nitroimidazol-2-yl)benzimidazole Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC2=CC=CC=C2N1CCCl YQKHOTXTHRUMHE-UHFFFAOYSA-N 0.000 description 2
- SFPBOUNVSUEKQZ-UHFFFAOYSA-N 2-[2-(1-methyl-5-nitroimidazol-2-yl)benzimidazol-1-yl]ethanol Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC2=CC=CC=C2N1CCO SFPBOUNVSUEKQZ-UHFFFAOYSA-N 0.000 description 2
- ZCZSDTVKVSBXHZ-UHFFFAOYSA-N 2-[2-(1h-benzimidazol-2-yl)-5-nitroimidazol-1-yl]ethanol Chemical compound C1=C([N+]([O-])=O)N(CCO)C(C=2NC3=CC=CC=C3N=2)=N1 ZCZSDTVKVSBXHZ-UHFFFAOYSA-N 0.000 description 2
- DJKXFTJVUBNUFJ-UHFFFAOYSA-N 2-[2-(1h-benzimidazol-2-yl)-5-nitroimidazol-1-yl]ethyl acetate Chemical compound CC(=O)OCCN1C([N+]([O-])=O)=CN=C1C1=NC2=CC=CC=C2N1 DJKXFTJVUBNUFJ-UHFFFAOYSA-N 0.000 description 2
- YMYPZBOBAISUFL-UHFFFAOYSA-N 2-n-[2-(dimethylamino)ethyl]benzene-1,2-diamine Chemical compound CN(C)CCNC1=CC=CC=C1N YMYPZBOBAISUFL-UHFFFAOYSA-N 0.000 description 2
- UJHUZYYVUDNZST-UHFFFAOYSA-N 4-[2-[2-(1-methyl-5-nitroimidazol-2-yl)benzimidazol-1-yl]ethyl]morpholine Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC2=CC=CC=C2N1CCN1CCOCC1 UJHUZYYVUDNZST-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- CDCUIKNWTWKVLW-UHFFFAOYSA-N hydrazine;palladium Chemical compound [Pd].NN CDCUIKNWTWKVLW-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Substances [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001256 steam distillation Methods 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 2
- SJLPSXHHPOFHGX-UHFFFAOYSA-N (1-butyl-5-nitroimidazol-2-yl)methanol Chemical compound CCCCN1C(CO)=NC=C1[N+]([O-])=O SJLPSXHHPOFHGX-UHFFFAOYSA-N 0.000 description 1
- NCYXNZNYAMKNKV-UHFFFAOYSA-N (1-ethyl-5-nitroimidazol-2-yl)methanol Chemical compound CCN1C(CO)=NC=C1[N+]([O-])=O NCYXNZNYAMKNKV-UHFFFAOYSA-N 0.000 description 1
- 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
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- UFXWIYRMEGCXIO-UHFFFAOYSA-N 2-(1-methyl-5-nitroimidazol-2-yl)-1-phenylbenzimidazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2N(C3=CC=CC=C3N=2)C=2C=CC=CC=2)=N1 UFXWIYRMEGCXIO-UHFFFAOYSA-N 0.000 description 1
- SKBVRDCOLMZAOE-UHFFFAOYSA-N 2-(1-methyl-5-nitroimidazol-2-yl)-3h-benzimidazole-5-carboxylic acid Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC2=CC=C(C(O)=O)C=C2N1 SKBVRDCOLMZAOE-UHFFFAOYSA-N 0.000 description 1
- PPSGIDLBEXCAPB-UHFFFAOYSA-N 2-(1-methyl-5-nitroimidazol-2-yl)-6-nitro-1h-benzimidazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2NC3=CC(=CC=C3N=2)[N+]([O-])=O)=N1 PPSGIDLBEXCAPB-UHFFFAOYSA-N 0.000 description 1
- BQJUEUXLAIHGPE-UHFFFAOYSA-N 2-(2-morpholin-4-ylethyl)aniline Chemical compound NC1=CC=CC=C1CCN1CCOCC1 BQJUEUXLAIHGPE-UHFFFAOYSA-N 0.000 description 1
- VKTQXDZZSCFRKT-UHFFFAOYSA-N 2-[2-(1-butyl-5-nitroimidazol-2-yl)benzimidazol-1-yl]-n,n-dimethylethanamine Chemical compound C1=C([N+]([O-])=O)N(CCCC)C(C=2N(C3=CC=CC=C3N=2)CCN(C)C)=N1 VKTQXDZZSCFRKT-UHFFFAOYSA-N 0.000 description 1
- TUJSZEWWFPTPLA-UHFFFAOYSA-N 2-[2-(1-ethyl-5-nitroimidazol-2-yl)benzimidazol-1-yl]-n,n-dimethylethanamine Chemical compound C1=C([N+]([O-])=O)N(CC)C(C=2N(C3=CC=CC=C3N=2)CCN(C)C)=N1 TUJSZEWWFPTPLA-UHFFFAOYSA-N 0.000 description 1
- XYWULVIJBZCESD-UHFFFAOYSA-N 2-[2-(1-methyl-5-nitroimidazol-2-yl)benzimidazol-1-yl]ethyl 4-methylbenzenesulfonate Chemical compound C1=CC(C)=CC=C1S(=O)(=O)OCCN1C2=CC=CC=C2N=C1C1=NC=C([N+]([O-])=O)N1C XYWULVIJBZCESD-UHFFFAOYSA-N 0.000 description 1
- VQSHBZFVYVAFEC-UHFFFAOYSA-N 2-[2-amino-4-(trifluoromethyl)anilino]ethanol Chemical compound NC1=CC(C(F)(F)F)=CC=C1NCCO VQSHBZFVYVAFEC-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
- LDOZLAKDJCZQKM-UHFFFAOYSA-N 2-n-[3-(dimethylamino)propyl]benzene-1,2-diamine Chemical compound CN(C)CCCNC1=CC=CC=C1N LDOZLAKDJCZQKM-UHFFFAOYSA-N 0.000 description 1
- RPKCLSMBVQLWIN-UHFFFAOYSA-N 2-n-methylbenzene-1,2-diamine Chemical compound CNC1=CC=CC=C1N RPKCLSMBVQLWIN-UHFFFAOYSA-N 0.000 description 1
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 1
- 150000004959 2-nitroimidazoles Chemical class 0.000 description 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
- UIKUBYKUYUSRSM-UHFFFAOYSA-N 3-morpholinopropylamine Chemical compound NCCCN1CCOCC1 UIKUBYKUYUSRSM-UHFFFAOYSA-N 0.000 description 1
- KCSALABEXYXQRB-UHFFFAOYSA-N 4-[3-[2-(1-methyl-5-nitroimidazol-2-yl)benzimidazol-1-yl]propyl]morpholine Chemical compound CN1C([N+]([O-])=O)=CN=C1C1=NC2=CC=CC=C2N1CCCN1CCOCC1 KCSALABEXYXQRB-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- SOJPHVHJVXTAHA-UHFFFAOYSA-N 5,6-diethoxy-2-(1-methyl-5-nitroimidazol-2-yl)-1h-benzimidazole Chemical compound N1C=2C=C(OCC)C(OCC)=CC=2N=C1C1=NC=C([N+]([O-])=O)N1C SOJPHVHJVXTAHA-UHFFFAOYSA-N 0.000 description 1
- OKYKMOWPBJDSKE-UHFFFAOYSA-N 5-methylcyclohexa-2,4-diene-1,1-diamine Chemical compound NC1(CC(=CC=C1)C)N OKYKMOWPBJDSKE-UHFFFAOYSA-N 0.000 description 1
- 150000004958 5-nitroimidazoles Chemical class 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 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
- 241001122767 Theaceae Species 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- GNNALEGJVYVIIH-UHFFFAOYSA-N benzene-1,2-diamine;hydrochloride Chemical compound Cl.NC1=CC=CC=C1N GNNALEGJVYVIIH-UHFFFAOYSA-N 0.000 description 1
- IYXMNTLBLQNMLM-UHFFFAOYSA-N benzene-1,4-diamine;hydron;dichloride Chemical compound Cl.Cl.NC1=CC=C(N)C=C1 IYXMNTLBLQNMLM-UHFFFAOYSA-N 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 230000029087 digestion Effects 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000003818 flash chromatography 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
- 239000005457 ice water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000002500 ions Chemical class 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 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
- DILRJUIACXKSQE-UHFFFAOYSA-N n',n'-dimethylethane-1,2-diamine Chemical compound CN(C)CCN DILRJUIACXKSQE-UHFFFAOYSA-N 0.000 description 1
- SIYLVOANDBQNPS-UHFFFAOYSA-N n-butyl-n-[3-[2-(1-methyl-5-nitroimidazol-2-yl)benzimidazol-1-yl]propyl]butan-1-amine Chemical compound N=1C2=CC=CC=C2N(CCCN(CCCC)CCCC)C=1C1=NC=C([N+]([O-])=O)N1C SIYLVOANDBQNPS-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
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229940072033 potash Drugs 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 238000005406 washing Methods 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)
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 (1)
| Publication Number | Publication Date |
|---|---|
| NO126624B true NO126624B (de) | 1973-03-05 |
Family
ID=5732064
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO01455/70A NO126624B (de) | 1969-04-19 | 1970-04-17 |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS4914231B1 (de) |
| AT (1) | AT294075B (de) |
| BE (1) | BE749102A (de) |
| CH (2) | CH546768A (de) |
| CS (1) | CS167896B2 (de) |
| DE (1) | DE1920635C3 (de) |
| DK (1) | DK137758B (de) |
| ES (1) | ES378368A1 (de) |
| FI (1) | FI52861C (de) |
| FR (1) | FR2042351B1 (de) |
| GB (1) | GB1312056A (de) |
| NL (1) | NL7005703A (de) |
| NO (1) | NO126624B (de) |
| SE (1) | SE364962B (de) |
| ZA (1) | ZA702577B (de) |
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/de not_active IP Right Cessation
- 1970-04-02 CH CH491970A patent/CH546774A/de 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 SE SE05326/70A patent/SE364962B/xx unknown
- 1970-04-17 AT AT351470A patent/AT294075B/de active
- 1970-04-17 NO NO01455/70A patent/NO126624B/no unknown
- 1970-04-17 BE BE749102D patent/BE749102A/xx unknown
- 1970-04-17 FR FR707013970A patent/FR2042351B1/fr not_active Expired
- 1970-04-17 ZA ZA702577A patent/ZA702577B/xx unknown
- 1970-04-17 FI FI701070A patent/FI52861C/fi active
- 1970-04-20 NL NL7005703A patent/NL7005703A/xx not_active Application Discontinuation
- 1970-04-20 GB GB1874370A patent/GB1312056A/en not_active Expired
- 1970-04-20 JP JP45033734A patent/JPS4914231B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| SE364962B (de) | 1974-03-11 |
| CH546768A (de) | 1974-03-15 |
| CS167896B2 (de) | 1976-05-28 |
| FR2042351A1 (de) | 1971-02-12 |
| CH546774A (de) | 1974-03-15 |
| BE749102A (fr) | 1970-10-19 |
| DE1920635A1 (de) | 1970-10-29 |
| ES378368A1 (es) | 1972-06-16 |
| DK137758B (da) | 1978-05-01 |
| GB1312056A (en) | 1973-04-04 |
| DE1920635B2 (de) | 1978-11-02 |
| AT294075B (de) | 1971-11-10 |
| NL7005703A (de) | 1970-10-21 |
| FI52861B (de) | 1977-08-31 |
| DE1920635C3 (de) | 1979-06-28 |
| FR2042351B1 (de) | 1973-07-13 |
| DK137758C (de) | 1978-10-09 |
| JPS4914231B1 (de) | 1974-04-05 |
| ZA702577B (en) | 1971-01-27 |
| FI52861C (fi) | 1977-12-12 |
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