NO135030B - - Google Patents
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- Publication number
- NO135030B NO135030B NO457972A NO457972A NO135030B NO 135030 B NO135030 B NO 135030B NO 457972 A NO457972 A NO 457972A NO 457972 A NO457972 A NO 457972A NO 135030 B NO135030 B NO 135030B
- Authority
- NO
- Norway
- Prior art keywords
- nitrofurylvinyl
- mol
- methyl
- present
- compounds
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 19
- JLMDCRSVWZKFHH-UHFFFAOYSA-N 1-[4-methyl-2-[2-(5-nitrofuran-2-yl)ethenyl]-1,3-thiazol-5-yl]ethanone Chemical compound CC1=C(C(=O)C)SC(C=CC=2OC(=CC=2)[N+]([O-])=O)=N1 JLMDCRSVWZKFHH-UHFFFAOYSA-N 0.000 claims description 13
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- SXINBFXPADXIEY-UHFFFAOYSA-N 5-Nitrofurfural Chemical compound [O-][N+](=O)C1=CC=C(C=O)O1 SXINBFXPADXIEY-UHFFFAOYSA-N 0.000 claims description 4
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 4
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 4
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- KJVBLCMUGHNZRT-UHFFFAOYSA-N 1-(1,4-dimethylpyrazol-3-yl)ethanone Chemical compound CC(=O)C1=NN(C)C=C1C KJVBLCMUGHNZRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- DUIOPKIIICUYRZ-UHFFFAOYSA-N semicarbazide Chemical compound NNC(N)=O DUIOPKIIICUYRZ-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 1
- 239000000243 solution Substances 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- 230000000845 anti-microbial effect Effects 0.000 description 13
- -1 nitrofuran-substituted thiazole Chemical class 0.000 description 13
- 239000013078 crystal Substances 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000004599 antimicrobial Substances 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000000921 elemental analysis Methods 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241000894006 Bacteria Species 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical class NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 4
- 239000001963 growth medium Substances 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000233866 Fungi Species 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229940027988 antiseptic and disinfectant nitrofuran derivative Drugs 0.000 description 3
- 235000010633 broth Nutrition 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 244000005700 microbiome Species 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 2
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241000544286 Vibrio anguillarum Species 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 2
- 235000018417 cysteine Nutrition 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000468 ketone group Chemical group 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VKGQPUZNCZPZKI-UHFFFAOYSA-N (diaminomethylideneamino)azanium;sulfate Chemical compound NN=C(N)N.NN=C(N)N.OS(O)(=O)=O VKGQPUZNCZPZKI-UHFFFAOYSA-N 0.000 description 1
- ANUKYNIYGCGGNK-UHFFFAOYSA-N 1-(2-methyl-1,3-thiazol-5-yl)ethanone Chemical class CC(=O)C1=CN=C(C)S1 ANUKYNIYGCGGNK-UHFFFAOYSA-N 0.000 description 1
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 description 1
- BLQOKWQUTLNKON-UHFFFAOYSA-N 5-Acetyl-2,4-dimethylthiazole Chemical compound CC(=O)C=1SC(C)=NC=1C BLQOKWQUTLNKON-UHFFFAOYSA-N 0.000 description 1
- UJTTUOLQLCQZEA-UHFFFAOYSA-N 9h-fluoren-9-ylmethyl n-(4-hydroxybutyl)carbamate Chemical compound C1=CC=C2C(COC(=O)NCCCCO)C3=CC=CC=C3C2=C1 UJTTUOLQLCQZEA-UHFFFAOYSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000607534 Aeromonas Species 0.000 description 1
- 241000252073 Anguilliformes Species 0.000 description 1
- 244000063299 Bacillus subtilis Species 0.000 description 1
- 235000014469 Bacillus subtilis Nutrition 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000004232 Enteritis Diseases 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- OQEDQUSPPJWKSX-UHFFFAOYSA-N N-(5-nitrofuran-2-yl)prop-2-enamide Chemical compound C(C=C)(=O)NC=1OC(=CC1)[N+](=O)[O-] OQEDQUSPPJWKSX-UHFFFAOYSA-N 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241000607598 Vibrio Species 0.000 description 1
- 230000005856 abnormality Effects 0.000 description 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- LEHOGBUBQSGCOK-UHFFFAOYSA-N aminothiourea;hydron;chloride Chemical compound Cl.NNC(N)=S LEHOGBUBQSGCOK-UHFFFAOYSA-N 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 230000034994 death Effects 0.000 description 1
- 231100000517 death Toxicity 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- DIPWSCBGTZZHJI-UHFFFAOYSA-N n-[1-(2,4-dimethyl-1,3-thiazol-5-yl)ethylidene]hydroxylamine Chemical compound ON=C(C)C=1SC(C)=NC=1C DIPWSCBGTZZHJI-UHFFFAOYSA-N 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229960001907 nitrofurazone Drugs 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000002504 physiological saline solution Substances 0.000 description 1
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229920000053 polysorbate 80 Polymers 0.000 description 1
- 238000004451 qualitative analysis Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000012488 sample solution Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 150000007979 thiazole derivatives Chemical class 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NO457972A NO135030C (enrdf_load_stackoverflow) | 1971-05-04 | 1972-12-12 |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP46029547A JPS5022093B1 (enrdf_load_stackoverflow) | 1971-05-04 | 1971-05-04 | |
| JP46029545A JPS4946619B1 (enrdf_load_stackoverflow) | 1971-05-04 | 1971-05-04 | |
| JP46029546A JPS4932852B1 (enrdf_load_stackoverflow) | 1971-05-04 | 1971-05-04 | |
| NO1550/72A NO135029C (enrdf_load_stackoverflow) | 1971-05-04 | 1972-05-03 | |
| NO457972A NO135030C (enrdf_load_stackoverflow) | 1971-05-04 | 1972-12-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO135030B true NO135030B (enrdf_load_stackoverflow) | 1976-10-18 |
| NO135030C NO135030C (enrdf_load_stackoverflow) | 1977-01-26 |
Family
ID=27521152
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO457972A NO135030C (enrdf_load_stackoverflow) | 1971-05-04 | 1972-12-12 |
Country Status (1)
| Country | Link |
|---|---|
| NO (1) | NO135030C (enrdf_load_stackoverflow) |
-
1972
- 1972-12-12 NO NO457972A patent/NO135030C/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO135030C (enrdf_load_stackoverflow) | 1977-01-26 |
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