NO127348B - - Google Patents
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- Publication number
- NO127348B NO127348B NO2694/70A NO269470A NO127348B NO 127348 B NO127348 B NO 127348B NO 2694/70 A NO2694/70 A NO 2694/70A NO 269470 A NO269470 A NO 269470A NO 127348 B NO127348 B NO 127348B
- Authority
- NO
- Norway
- Prior art keywords
- group
- carbon atoms
- nitro
- methyl
- imidazolyl
- Prior art date
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 126
- 229910052739 hydrogen Inorganic materials 0.000 claims description 124
- -1 2-benzoyloxyethyl group Chemical group 0.000 claims description 75
- 125000004432 carbon atom Chemical group C* 0.000 claims description 50
- 150000001875 compounds Chemical class 0.000 claims description 25
- 229910052717 sulfur Inorganic materials 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000003277 amino group Chemical group 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000002431 aminoalkoxy group Chemical group 0.000 claims description 4
- 150000002366 halogen compounds Chemical class 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000007933 aliphatic carboxylic acids Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical class 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- 125000005333 aroyloxy group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 239000012467 final product Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims description 2
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 2
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 claims 1
- 150000008052 alkyl sulfonates Chemical class 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 230000000845 anti-microbial effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000008050 dialkyl sulfates Chemical class 0.000 claims 1
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims 1
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims 1
- 238000002844 melting Methods 0.000 description 147
- 230000008018 melting Effects 0.000 description 146
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 60
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 44
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- 238000001816 cooling Methods 0.000 description 21
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- 229960000583 acetic acid Drugs 0.000 description 18
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 238000001953 recrystallisation Methods 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 12
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
- 239000012362 glacial acetic acid Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- ZRKQOVXGDIZYDS-UHFFFAOYSA-N 5-hydroxy-2,3-dihydroinden-1-one Chemical compound OC1=CC=C2C(=O)CCC2=C1 ZRKQOVXGDIZYDS-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
- 235000011054 acetic acid Nutrition 0.000 description 8
- QOPRWBRNMPANKN-UHFFFAOYSA-N 5-methoxy-2,3-dihydroinden-1-one Chemical compound COC1=CC=C2C(=O)CCC2=C1 QOPRWBRNMPANKN-UHFFFAOYSA-N 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 235000011121 sodium hydroxide Nutrition 0.000 description 7
- 239000012265 solid product Substances 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 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 5
- 230000029087 digestion Effects 0.000 description 5
- 239000012071 phase Substances 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 4
- CKPZRIYEXNKFLL-UHFFFAOYSA-N 5-methoxy-2-[(1-methyl-5-nitroimidazol-2-yl)methylidene]-3H-inden-1-one Chemical compound COC=1C=C2CC(C(C2=CC1)=O)=CC=1N(C(=CN1)[N+](=O)[O-])C CKPZRIYEXNKFLL-UHFFFAOYSA-N 0.000 description 4
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- GHUPGGYDRVSZSW-UHFFFAOYSA-N n-(1-oxo-2,3-dihydroinden-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2C(=O)CCC2=C1 GHUPGGYDRVSZSW-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- WQMAANNAZKNUDL-UHFFFAOYSA-N 2-dimethylaminoethyl chloride Chemical compound CN(C)CCCl WQMAANNAZKNUDL-UHFFFAOYSA-N 0.000 description 3
- IJCQVTSNIBWXLF-UHFFFAOYSA-N 5-(2-hydroxyethoxy)-2,3-dihydroinden-1-one Chemical compound OCCOC=1C=C2CCC(C2=CC1)=O IJCQVTSNIBWXLF-UHFFFAOYSA-N 0.000 description 3
- 150000008064 anhydrides Chemical class 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 3
- 229960000282 metronidazole Drugs 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- GAGUQISURGFYNC-UHFFFAOYSA-N 1-[4-(2-hydroxyethoxy)phenyl]ethanone Chemical compound CC(=O)C1=CC=C(OCCO)C=C1 GAGUQISURGFYNC-UHFFFAOYSA-N 0.000 description 2
- HUDYANRNMZDQGA-UHFFFAOYSA-N 1-[4-(dimethylamino)phenyl]ethanone Chemical compound CN(C)C1=CC=C(C(C)=O)C=C1 HUDYANRNMZDQGA-UHFFFAOYSA-N 0.000 description 2
- GIJREQFJZFXMBZ-UHFFFAOYSA-N 1-[4-[2-(dimethylamino)ethoxy]phenyl]ethanone;hydrochloride Chemical compound Cl.CN(C)CCOC1=CC=C(C(C)=O)C=C1 GIJREQFJZFXMBZ-UHFFFAOYSA-N 0.000 description 2
- UMSMQVJJULFTFY-UHFFFAOYSA-N 2-[(1-methyl-5-nitroimidazol-2-yl)methylidene]-3H-inden-1-one Chemical compound [N+](=O)([O-])C1=CN=C(N1C)C=C1C(C2=CC=CC=C2C1)=O UMSMQVJJULFTFY-UHFFFAOYSA-N 0.000 description 2
- XUUOYQOKQATGRR-UHFFFAOYSA-N 2-[[2-[(1-methyl-5-nitroimidazol-2-yl)methylidene]-1-oxo-3H-inden-5-yl]oxy]ethyl acetate Chemical compound C(C)(=O)OCCOC=1C=C2CC(C(C2=CC1)=O)=CC=1N(C(=CN1)[N+](=O)[O-])C XUUOYQOKQATGRR-UHFFFAOYSA-N 0.000 description 2
- LDLCZOVUSADOIV-UHFFFAOYSA-N 2-bromoethanol Chemical compound OCCBr LDLCZOVUSADOIV-UHFFFAOYSA-N 0.000 description 2
- OOIVTNPWFIHCAL-UHFFFAOYSA-N 3-(1-methyl-5-nitroimidazol-2-yl)-1-phenylprop-2-en-1-one Chemical compound [N+](=O)([O-])C1=CN=C(N1C)C=CC(=O)C1=CC=CC=C1 OOIVTNPWFIHCAL-UHFFFAOYSA-N 0.000 description 2
- XVTQSYKCADSUHN-UHFFFAOYSA-N 3-methyl-2,3-dihydroinden-1-one Chemical compound C1=CC=C2C(C)CC(=O)C2=C1 XVTQSYKCADSUHN-UHFFFAOYSA-N 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
- CKSCMRNFDBWFND-UHFFFAOYSA-N 4-hydroxy-2,3-dihydroinden-1-one Chemical compound OC1=CC=CC2=C1CCC2=O CKSCMRNFDBWFND-UHFFFAOYSA-N 0.000 description 2
- RUORWXQKVXTQJJ-UHFFFAOYSA-N 4-methyl-2,3-dihydroinden-1-one Chemical compound CC1=CC=CC2=C1CCC2=O RUORWXQKVXTQJJ-UHFFFAOYSA-N 0.000 description 2
- LLTZGIHNPKZNHN-UHFFFAOYSA-N 5-(2-hydroxyethoxy)-2-[(1-methyl-5-nitroimidazol-2-yl)methylidene]-3H-inden-1-one Chemical compound OCCOC=1C=C2CC(C(C2=CC1)=O)=CC=1N(C(=CN1)[N+](=O)[O-])C LLTZGIHNPKZNHN-UHFFFAOYSA-N 0.000 description 2
- WXEPAQXYMRRCSL-UHFFFAOYSA-N 5-(2-piperidin-1-ylethoxy)-2,3-dihydroinden-1-one hydrochloride Chemical compound Cl.N1(CCCCC1)CCOC=1C=C2CCC(C2=CC1)=O WXEPAQXYMRRCSL-UHFFFAOYSA-N 0.000 description 2
- XXAWPKPQMFWGTQ-UHFFFAOYSA-N 5-(dimethylamino)-2,3-dihydroinden-1-one Chemical compound CN(C)C1=CC=C2C(=O)CCC2=C1 XXAWPKPQMFWGTQ-UHFFFAOYSA-N 0.000 description 2
- XLQKISIXNZMCOT-UHFFFAOYSA-N 5-[2-(diethylamino)ethoxy]-2,3-dihydroinden-1-one hydrochloride Chemical compound Cl.C(C)N(CCOC=1C=C2CCC(C2=CC1)=O)CC XLQKISIXNZMCOT-UHFFFAOYSA-N 0.000 description 2
- HODOSJNSRPXYBH-UHFFFAOYSA-N 5-amino-2,3-dihydroinden-1-one Chemical compound NC1=CC=C2C(=O)CCC2=C1 HODOSJNSRPXYBH-UHFFFAOYSA-N 0.000 description 2
- PMRNLVGKMGUYCZ-UHFFFAOYSA-N 5-hydroxy-2-[(1-methyl-5-nitroimidazol-2-yl)methylidene]-3H-inden-1-one Chemical compound OC=1C=C2CC(C(C2=CC1)=O)=CC=1N(C(=CN1)[N+](=O)[O-])C PMRNLVGKMGUYCZ-UHFFFAOYSA-N 0.000 description 2
- 150000004958 5-nitroimidazoles Chemical class 0.000 description 2
- NUOWVWNBAMQRFR-UHFFFAOYSA-N 6-(2-hydroxyethoxy)-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(OCCO)=CC=C21 NUOWVWNBAMQRFR-UHFFFAOYSA-N 0.000 description 2
- KLJWFFXNAZUXFJ-UHFFFAOYSA-N 6-(dimethylamino)-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(N(C)C)=CC=C21 KLJWFFXNAZUXFJ-UHFFFAOYSA-N 0.000 description 2
- ZXGAPAUXCAUXDW-UHFFFAOYSA-N 6-(methylamino)-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(NC)=CC=C21 ZXGAPAUXCAUXDW-UHFFFAOYSA-N 0.000 description 2
- IBGSTOWDILMEHA-UHFFFAOYSA-N 6-amino-2-[(1-methyl-5-nitroimidazol-2-yl)methylidene]-3,4-dihydronaphthalen-1-one Chemical compound NC=1C=C2CCC(C(C2=CC1)=O)=CC=1N(C(=CN1)[N+](=O)[O-])C IBGSTOWDILMEHA-UHFFFAOYSA-N 0.000 description 2
- GBDMODVZBPFQKI-UHFFFAOYSA-N 6-hydroxy-1-benzofuran-3-one Chemical compound OC1=CC=C2C(=O)COC2=C1 GBDMODVZBPFQKI-UHFFFAOYSA-N 0.000 description 2
- FNSQPQKPPGALFA-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(O)=CC=C21 FNSQPQKPPGALFA-UHFFFAOYSA-N 0.000 description 2
- DBOXRDYLMJMQBB-UHFFFAOYSA-N 6-methyl-2,3-dihydroinden-1-one Chemical compound CC1=CC=C2CCC(=O)C2=C1 DBOXRDYLMJMQBB-UHFFFAOYSA-N 0.000 description 2
- XJWBVGDAFGVJEG-UHFFFAOYSA-N 7-hydroxy-2,3-dihydrochromen-4-one Chemical compound O=C1CCOC2=CC(O)=CC=C21 XJWBVGDAFGVJEG-UHFFFAOYSA-N 0.000 description 2
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- NAVKVJHCJPCNJR-UHFFFAOYSA-N C(C)(=O)NC1=CC=C(C=C1)C(C=CC=1N(C(=CN1)[N+](=O)[O-])C)=O Chemical compound C(C)(=O)NC1=CC=C(C=C1)C(C=CC=1N(C(=CN1)[N+](=O)[O-])C)=O NAVKVJHCJPCNJR-UHFFFAOYSA-N 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Chemical compound 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 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ODUMTQBXNCKRFL-UHFFFAOYSA-N N-[2-[(1-methyl-5-nitroimidazol-2-yl)methylidene]-1-oxo-3H-inden-5-yl]acetamide Chemical compound C(C)(=O)NC=1C=C2CC(C(C2=CC1)=O)=CC=1N(C(=CN1)[N+](=O)[O-])C ODUMTQBXNCKRFL-UHFFFAOYSA-N 0.000 description 2
- WXBPPTKUSWCKBV-UHFFFAOYSA-N N-[6-[(1-methyl-5-nitroimidazol-2-yl)methylidene]-5-oxo-7,8-dihydronaphthalen-2-yl]acetamide Chemical compound C(C)(=O)NC=1C=C2CCC(C(C2=CC1)=O)=CC=1N(C(=CN1)[N+](=O)[O-])C WXBPPTKUSWCKBV-UHFFFAOYSA-N 0.000 description 2
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 229930040373 Paraformaldehyde Natural products 0.000 description 2
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- ZIXYEABWUGPELQ-UHFFFAOYSA-N acetonitrile chloroform oxolane Chemical compound O1CCCC1.C(Cl)(Cl)Cl.C(C)#N ZIXYEABWUGPELQ-UHFFFAOYSA-N 0.000 description 1
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- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
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- 235000011389 fruit/vegetable juice Nutrition 0.000 description 1
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- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- WWECJGLXBSQKRF-UHFFFAOYSA-N n,n-dimethylformamide;methanol Chemical compound OC.CN(C)C=O WWECJGLXBSQKRF-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
- C07C45/70—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form
- C07C45/71—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction with functional groups containing oxygen only in singly bound form being hydroxy groups
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691935685 DE1935685A1 (de) | 1969-07-10 | 1969-07-10 | Neue antimikrobiell wirksame Verbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO127348B true NO127348B (pl) | 1973-06-12 |
Family
ID=5739764
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO2694/70A NO127348B (pl) | 1969-07-10 | 1970-07-09 |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3721668A (pl) |
| JP (1) | JPS52948B1 (pl) |
| AT (1) | AT295523B (pl) |
| BE (1) | BE753277A (pl) |
| CA (1) | CA919181A (pl) |
| CH (1) | CH547290A (pl) |
| DE (1) | DE1935685A1 (pl) |
| EG (1) | EG10938A (pl) |
| ES (1) | ES381633A1 (pl) |
| FR (1) | FR2059500B1 (pl) |
| GB (1) | GB1320712A (pl) |
| IL (1) | IL34881A (pl) |
| NL (1) | NL7010291A (pl) |
| NO (1) | NO127348B (pl) |
| PL (1) | PL81333B1 (pl) |
| SE (1) | SE387115B (pl) |
| SU (1) | SU365886A3 (pl) |
| ZA (1) | ZA704381B (pl) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3989832A (en) * | 1972-04-01 | 1976-11-02 | Boehringer Mannheim G.M.B.H. | Combating bacteria with nitroimidazolyl-triazolo-pyridiazine compounds |
| PL84022B1 (pl) * | 1972-04-01 | 1976-02-28 | ||
| US4086351A (en) * | 1975-10-09 | 1978-04-25 | Imperial Chemical Industries Limited | 1,2,4-Triazole-containing compounds and their use as pesticides |
| US4087536A (en) * | 1976-05-04 | 1978-05-02 | The Dow Chemical Company | Method for the use of thienylvinylimidazoles as anthelmintics |
| US4067989A (en) * | 1976-05-07 | 1978-01-10 | Imperial Chemical Industries Limited | 1,3-Diazole heterocyclic compounds and their use as pesticides |
| GB2060611A (en) * | 1979-08-08 | 1981-05-07 | Squibb & Sons Inc | 2,3-Dihydro-4H-1- benzothiopyran-4-ones and 2,3- dihydro-1H-inden-1-ones |
| US4273776A (en) * | 1980-01-30 | 1981-06-16 | E. R. Squibb & Sons, Inc. | Antibacterial and antifungal derivatives of 3-(1H-imidazol-1-yl)-2-propen-1-ones |
| US5158943A (en) * | 1988-11-21 | 1992-10-27 | Takeda Chemical Industries, Ltd. | Sulfur-containing heterocyclic compounds |
| NZ231939A (en) * | 1988-12-28 | 1991-07-26 | Takeda Chemical Industries Ltd | Benzothiopyran derivatives and medicaments |
| JP2001510801A (ja) * | 1997-07-25 | 2001-08-07 | フィテラ インク． | 置換アウロン誘導体 |
| DE69805596T2 (de) * | 1997-12-16 | 2002-11-28 | Ssp Co., Ltd. | Imidazol-Derivat und dieses als aktiven Bestandteil enthaltendes Arzneimittel |
| WO2000018231A1 (en) * | 1998-09-25 | 2000-04-06 | Viropharma Incorporated | Methods for treating or preventing viral infections and associated diseases |
| US20040154264A1 (en) * | 2000-08-04 | 2004-08-12 | Colbert Elizabeth A. | Coated gypsum board products and method of manufacture |
| CN103483476B (zh) * | 2012-06-13 | 2017-02-22 | 中国石油化工股份有限公司 | 一种抗菌高分子聚合物及其制备方法和应用 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1480662A (fr) * | 1965-10-07 | 1967-05-12 | Pfizer & Co C | Perfectionnements aux procédés pour la préparation de vinyl-amidines cycliques substituées |
| AT277985B (de) * | 1967-11-14 | 1970-01-12 | Schering Ag | Verfahren zur Herstellung von neuen Nitro-furan-, -thiophen- oder -pyrrol-derivaten |
-
1969
- 1969-07-10 DE DE19691935685 patent/DE1935685A1/de active Pending
-
1970
- 1970-06-25 ZA ZA704381A patent/ZA704381B/xx unknown
- 1970-07-02 SU SU1454753A patent/SU365886A3/ru active
- 1970-07-03 SE SE7009299A patent/SE387115B/xx unknown
- 1970-07-04 EG EG304/70A patent/EG10938A/xx active
- 1970-07-08 US US00053298A patent/US3721668A/en not_active Expired - Lifetime
- 1970-07-08 PL PL1970141917A patent/PL81333B1/pl unknown
- 1970-07-08 GB GB3317870A patent/GB1320712A/en not_active Expired
- 1970-07-09 FR FR7025515A patent/FR2059500B1/fr not_active Expired
- 1970-07-09 AT AT626270A patent/AT295523B/de not_active IP Right Cessation
- 1970-07-09 IL IL34881A patent/IL34881A/en unknown
- 1970-07-09 ES ES381633A patent/ES381633A1/es not_active Expired
- 1970-07-09 NO NO2694/70A patent/NO127348B/no unknown
- 1970-07-10 BE BE753277D patent/BE753277A/xx unknown
- 1970-07-10 CA CA087898A patent/CA919181A/en not_active Expired
- 1970-07-10 NL NL7010291A patent/NL7010291A/xx unknown
- 1970-07-10 JP JP45060553A patent/JPS52948B1/ja active Pending
- 1970-07-10 CH CH1054470A patent/CH547290A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| IL34881A0 (en) | 1971-02-25 |
| GB1320712A (en) | 1973-06-20 |
| SE387115B (sv) | 1976-08-30 |
| FR2059500B1 (pl) | 1974-02-01 |
| PL81333B1 (pl) | 1975-08-30 |
| AT295523B (de) | 1972-01-10 |
| ES381633A1 (es) | 1972-12-01 |
| FR2059500A1 (pl) | 1971-06-04 |
| SU365886A3 (pl) | 1973-01-08 |
| DE1935685A1 (de) | 1971-01-14 |
| NL7010291A (pl) | 1971-01-12 |
| US3721668A (en) | 1973-03-20 |
| BE753277A (fr) | 1971-01-11 |
| CA919181A (en) | 1973-01-16 |
| ZA704381B (en) | 1971-03-31 |
| JPS52948B1 (pl) | 1977-01-11 |
| CH547290A (de) | 1974-03-29 |
| EG10938A (en) | 1976-10-31 |
| IL34881A (en) | 1974-07-31 |
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