IL45073A - 3-(5-nitro-imidazol-2-yl)pyrazoles - Google Patents
3-(5-nitro-imidazol-2-yl)pyrazolesInfo
- Publication number
- IL45073A IL45073A IL45073A IL4507374A IL45073A IL 45073 A IL45073 A IL 45073A IL 45073 A IL45073 A IL 45073A IL 4507374 A IL4507374 A IL 4507374A IL 45073 A IL45073 A IL 45073A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- methyl
- preparing
- comprises reacting
- pyrazole
- Prior art date
Links
- RYDKGFCJYKHGGB-UHFFFAOYSA-N 5-nitro-2-(1H-pyrazol-5-yl)-1H-imidazole Chemical class N1C([N+](=O)[O-])=CN=C1C1=NNC=C1 RYDKGFCJYKHGGB-UHFFFAOYSA-N 0.000 title 1
- 241000606856 Pasteurella multocida Species 0.000 claims abstract description 17
- 229940051027 pasteurella multocida Drugs 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 7
- 241000588724 Escherichia coli Species 0.000 claims abstract description 6
- 150000001875 compounds Chemical class 0.000 claims description 108
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 51
- 238000000034 method Methods 0.000 claims description 47
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 28
- 230000008569 process Effects 0.000 claims description 24
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 16
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 15
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 13
- 238000002360 preparation method Methods 0.000 claims description 13
- 208000015181 infectious disease Diseases 0.000 claims description 11
- 239000002253 acid Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 9
- 244000144977 poultry Species 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 241000894006 Bacteria Species 0.000 claims description 5
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 claims description 5
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 claims description 4
- HYBBIBNJHNGZAN-UHFFFAOYSA-N furfural Chemical compound O=CC1=CC=CO1 HYBBIBNJHNGZAN-UHFFFAOYSA-N 0.000 claims description 4
- 150000002905 orthoesters Chemical class 0.000 claims description 4
- SATCULPHIDQDRE-UHFFFAOYSA-N piperonal Chemical compound O=CC1=CC=C2OCOC2=C1 SATCULPHIDQDRE-UHFFFAOYSA-N 0.000 claims description 4
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- CEIPQQODRKXDSB-UHFFFAOYSA-N ethyl 3-(6-hydroxynaphthalen-2-yl)-1H-indazole-5-carboximidate dihydrochloride Chemical compound Cl.Cl.C1=C(O)C=CC2=CC(C3=NNC4=CC=C(C=C43)C(=N)OCC)=CC=C21 CEIPQQODRKXDSB-UHFFFAOYSA-N 0.000 claims description 3
- 230000002140 halogenating effect Effects 0.000 claims description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 150000001299 aldehydes Chemical class 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 150000001408 amides Chemical class 0.000 claims description 2
- 150000008064 anhydrides Chemical class 0.000 claims description 2
- 230000003301 hydrolyzing effect Effects 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 claims description 2
- 229940081310 piperonal Drugs 0.000 claims description 2
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- HFFLGKNGCAIQMO-UHFFFAOYSA-N trichloroacetaldehyde Chemical compound ClC(Cl)(Cl)C=O HFFLGKNGCAIQMO-UHFFFAOYSA-N 0.000 claims 2
- KJPRLNWUNMBNBZ-QPJJXVBHSA-N (E)-cinnamaldehyde Chemical compound O=C\C=C\C1=CC=CC=C1 KJPRLNWUNMBNBZ-QPJJXVBHSA-N 0.000 claims 1
- MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical compound FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 claims 1
- 241000607142 Salmonella Species 0.000 claims 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 150000002825 nitriles Chemical class 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 229910000104 sodium hydride Inorganic materials 0.000 claims 1
- 239000012312 sodium hydride Substances 0.000 claims 1
- 238000007920 subcutaneous administration Methods 0.000 claims 1
- 229940029273 trichloroacetaldehyde Drugs 0.000 claims 1
- -1 3,4-methylenedioxyphenyl Chemical group 0.000 abstract description 47
- 125000000217 alkyl group Chemical group 0.000 abstract description 16
- 241000589886 Treponema Species 0.000 abstract description 8
- 241000293869 Salmonella enterica subsp. enterica serovar Typhimurium Species 0.000 abstract description 7
- 230000000844 anti-bacterial effect Effects 0.000 abstract description 4
- 229940088710 antibiotic agent Drugs 0.000 abstract description 3
- 229940121375 antifungal agent Drugs 0.000 abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 abstract description 3
- 208000003495 Coccidiosis Diseases 0.000 abstract description 2
- 206010023076 Isosporiasis Diseases 0.000 abstract description 2
- 230000000842 anti-protozoal effect Effects 0.000 abstract description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 2
- 125000001589 carboacyl group Chemical group 0.000 abstract 2
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 229940036589 antiprotozoals Drugs 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 125000006238 prop-1-en-1-yl group Chemical group [H]\C(*)=C(/[H])C([H])([H])[H] 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 69
- 238000012360 testing method Methods 0.000 description 44
- 239000000047 product Substances 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000007795 chemical reaction product Substances 0.000 description 28
- 238000002844 melting Methods 0.000 description 28
- 230000008018 melting Effects 0.000 description 28
- 239000007787 solid Substances 0.000 description 28
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- 238000000921 elemental analysis Methods 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 23
- 241000699670 Mus sp. Species 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- 241000287828 Gallus gallus Species 0.000 description 17
- 241000282887 Suidae Species 0.000 description 17
- 235000013330 chicken meat Nutrition 0.000 description 17
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 17
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 241000286209 Phasianidae Species 0.000 description 13
- 241000282898 Sus scrofa Species 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 238000010790 dilution Methods 0.000 description 12
- 239000012895 dilution Substances 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 11
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- 238000002474 experimental method Methods 0.000 description 9
- 230000003902 lesion Effects 0.000 description 8
- 239000000725 suspension Substances 0.000 description 8
- UCDBLYHPJMMFMY-UHFFFAOYSA-N 8-bromoquinoline-4-carbonitrile Chemical compound C1=CN=C2C(Br)=CC=CC2=C1C#N UCDBLYHPJMMFMY-UHFFFAOYSA-N 0.000 description 7
- 208000001848 dysentery Diseases 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 150000007857 hydrazones Chemical class 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 241000283690 Bos taurus Species 0.000 description 6
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 241000699666 Mus <mouse, genus> Species 0.000 description 6
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 6
- 239000012346 acetyl chloride Substances 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 6
- CUONGYYJJVDODC-UHFFFAOYSA-N malononitrile Chemical compound N#CCC#N CUONGYYJJVDODC-UHFFFAOYSA-N 0.000 description 6
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- 241001148471 unidentified anaerobic bacterium Species 0.000 description 6
- KJTRXVXWSSPHRV-UHFFFAOYSA-N 4-benzoyl-5-methyl-2-phenyl-1h-pyrazol-3-one Chemical compound O=C1C(C(=O)C=2C=CC=CC=2)=C(C)NN1C1=CC=CC=C1 KJTRXVXWSSPHRV-UHFFFAOYSA-N 0.000 description 5
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- 229940086542 triethylamine Drugs 0.000 description 5
- 229920001817 Agar Polymers 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- MJVAVZPDRWSRRC-UHFFFAOYSA-N Menadione Chemical compound C1=CC=C2C(=O)C(C)=CC(=O)C2=C1 MJVAVZPDRWSRRC-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000004083 survival effect Effects 0.000 description 4
- 238000004809 thin layer chromatography Methods 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- 238000005303 weighing Methods 0.000 description 4
- JLQLFVSTEDRFAD-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbaldehyde Chemical compound CN1C(C=O)=NC=C1[N+]([O-])=O JLQLFVSTEDRFAD-UHFFFAOYSA-N 0.000 description 3
- 241000606125 Bacteroides Species 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
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- 235000021053 average weight gain Nutrition 0.000 description 3
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- XIURVHNZVLADCM-IUODEOHRSA-N cefalotin Chemical compound N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)C(=O)CC1=CC=CS1 XIURVHNZVLADCM-IUODEOHRSA-N 0.000 description 3
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- 238000011049 filling Methods 0.000 description 3
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 238000011534 incubation Methods 0.000 description 3
- 210000003097 mucus Anatomy 0.000 description 3
- OCLUTMPYMSWFNN-UHFFFAOYSA-N n,1-dimethyl-5-nitroimidazole-2-carbohydrazonoyl bromide Chemical compound CNN=C(Br)C1=NC=C([N+]([O-])=O)N1C OCLUTMPYMSWFNN-UHFFFAOYSA-N 0.000 description 3
- 150000004957 nitroimidazoles Chemical class 0.000 description 3
- 229920003023 plastic Polymers 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 125000004497 pyrazol-5-yl group Chemical group N1N=CC=C1* 0.000 description 3
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- NDQXKKFRNOPRDW-UHFFFAOYSA-N 1,1,1-triethoxyethane Chemical compound CCOC(C)(OCC)OCC NDQXKKFRNOPRDW-UHFFFAOYSA-N 0.000 description 2
- SGJBIFUEFLWXJY-UHFFFAOYSA-N 1-(dibutoxymethoxy)butane Chemical compound CCCCOC(OCCCC)OCCCC SGJBIFUEFLWXJY-UHFFFAOYSA-N 0.000 description 2
- GBHCABUWWQUMAJ-UHFFFAOYSA-N 2-hydrazinoethanol Chemical compound NNCCO GBHCABUWWQUMAJ-UHFFFAOYSA-N 0.000 description 2
- HLXQFJWWTNYPFM-UHFFFAOYSA-N 2-methyl-5-(1-methyl-5-nitroimidazol-2-yl)pyrazol-3-amine Chemical compound C1=C(N)N(C)N=C1C1=NC=C([N+]([O-])=O)N1C HLXQFJWWTNYPFM-UHFFFAOYSA-N 0.000 description 2
- FUBFWTUFPGFHOJ-UHFFFAOYSA-N 2-nitrofuran Chemical class [O-][N+](=O)C1=CC=CO1 FUBFWTUFPGFHOJ-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
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- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 238000011887 Necropsy Methods 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
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- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- OWPQUQSVZURPSP-UHFFFAOYSA-N n-[(1-methyl-5-nitroimidazol-2-yl)methylideneamino]methanamine Chemical compound CNN=CC1=NC=C([N+]([O-])=O)N1C OWPQUQSVZURPSP-UHFFFAOYSA-N 0.000 description 2
- 238000005949 ozonolysis reaction Methods 0.000 description 2
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- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000007143 thioglycolate medium Substances 0.000 description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 2
- PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
- 239000006150 trypticase soy agar Substances 0.000 description 2
- 235000012711 vitamin K3 Nutrition 0.000 description 2
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- 229940041603 vitamin k 3 Drugs 0.000 description 2
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- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 description 1
- FGWYWKIOMUZSQF-UHFFFAOYSA-N 1,1,1-triethoxypropane Chemical compound CCOC(CC)(OCC)OCC FGWYWKIOMUZSQF-UHFFFAOYSA-N 0.000 description 1
- JAFMOTJMRSZOJE-UHFFFAOYSA-N 1,1,1-trimethoxybutane Chemical compound CCCC(OC)(OC)OC JAFMOTJMRSZOJE-UHFFFAOYSA-N 0.000 description 1
- SOGRNDDWNKIUHI-UHFFFAOYSA-N 1,1,1-tripropoxybutane Chemical compound CCCOC(CCC)(OCCC)OCCC SOGRNDDWNKIUHI-UHFFFAOYSA-N 0.000 description 1
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- UOCJDOLVGGIYIQ-PBFPGSCMSA-N cefatrizine Chemical group S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)[C@H](N)C=2C=CC(O)=CC=2)CC=1CSC=1C=NNN=1 UOCJDOLVGGIYIQ-PBFPGSCMSA-N 0.000 description 1
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- 239000002026 chloroform extract Substances 0.000 description 1
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- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- WHRIKZCFRVTHJH-UHFFFAOYSA-N ethylhydrazine Chemical compound CCNN WHRIKZCFRVTHJH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
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- 238000001030 gas--liquid chromatography Methods 0.000 description 1
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- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
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- 125000004970 halomethyl group Chemical group 0.000 description 1
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- BTIJJDXEELBZFS-QDUVMHSLSA-K hemin Chemical compound CC1=C(CCC(O)=O)C(C=C2C(CCC(O)=O)=C(C)\C(N2[Fe](Cl)N23)=C\4)=N\C1=C/C2=C(C)C(C=C)=C3\C=C/1C(C)=C(C=C)C/4=N\1 BTIJJDXEELBZFS-QDUVMHSLSA-K 0.000 description 1
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- 239000002054 inoculum Substances 0.000 description 1
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- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000011005 laboratory method Methods 0.000 description 1
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- 235000019341 magnesium sulphate Nutrition 0.000 description 1
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- 150000004682 monohydrates Chemical class 0.000 description 1
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- OENWLPVOSVIKOJ-UHFFFAOYSA-N n,n-diethyl-2-methyl-5-(1-methyl-5-nitroimidazol-2-yl)pyrazol-3-amine Chemical compound CN1C(N(CC)CC)=CC(C=2N(C(=CN=2)[N+]([O-])=O)C)=N1 OENWLPVOSVIKOJ-UHFFFAOYSA-N 0.000 description 1
- WQVHUKJEGJTYOW-UHFFFAOYSA-N n-[(1-methyl-5-nitroimidazol-2-yl)methylideneamino]ethanamine Chemical compound CCNN=CC1=NC=C([N+]([O-])=O)N1C WQVHUKJEGJTYOW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- ATXLENZWWDUZLH-UHFFFAOYSA-N oxalic acid;propylhydrazine Chemical compound CCCNN.OC(=O)C(O)=O ATXLENZWWDUZLH-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
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- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- WKFBZNUBXWCCHG-UHFFFAOYSA-N phosphorus trifluoride Chemical compound FP(F)F WKFBZNUBXWCCHG-UHFFFAOYSA-N 0.000 description 1
- 201000006509 pleuropneumonia Diseases 0.000 description 1
- KJAQRHMKLVGSCG-UHFFFAOYSA-N propan-2-ylhydrazine Chemical compound CC(C)NN KJAQRHMKLVGSCG-UHFFFAOYSA-N 0.000 description 1
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical class CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 230000005180 public health Effects 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 239000001540 sodium lactate Substances 0.000 description 1
- 235000011088 sodium lactate Nutrition 0.000 description 1
- 229940005581 sodium lactate Drugs 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 239000002690 trypanocidal agent Substances 0.000 description 1
- 230000000654 trypanocidal effect Effects 0.000 description 1
- 201000002311 trypanosomiasis Diseases 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23K—FODDER
- A23K20/00—Accessory food factors for animal feeding-stuffs
- A23K20/10—Organic substances
- A23K20/116—Heterocyclic compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Polymers & Plastics (AREA)
- Animal Husbandry (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US38513673A | 1973-08-02 | 1973-08-02 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL45073A0 IL45073A0 (en) | 1974-09-10 |
| IL45073A true IL45073A (en) | 1977-07-31 |
Family
ID=23520163
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL45073A IL45073A (en) | 1973-08-02 | 1974-06-20 | 3-(5-nitro-imidazol-2-yl)pyrazoles |
Country Status (18)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2014268700B2 (en) * | 2013-05-20 | 2018-07-05 | University Of Washington Through Its Center For Commercialization | 5-aminopyrazole-4-carboxamide inhibitors of CDPK1 from T. gondii and C. parvum |
-
1974
- 1974-06-18 ZA ZA00743887A patent/ZA743887B/xx unknown
- 1974-06-20 IL IL45073A patent/IL45073A/en unknown
- 1974-07-02 DE DE2431775A patent/DE2431775A1/de active Pending
- 1974-07-24 RO RO7400079581A patent/RO63973A/ro unknown
- 1974-07-25 NL NL7410033A patent/NL7410033A/xx unknown
- 1974-07-29 AR AR254925A patent/AR203854A1/es active
- 1974-07-29 DD DD180187A patent/DD112759A5/xx unknown
- 1974-07-31 AT AT627474A patent/AT337691B/de not_active IP Right Cessation
- 1974-08-01 BR BR6317/74A patent/BR7406317D0/pt unknown
- 1974-08-01 JP JP49088635A patent/JPS5047978A/ja active Pending
- 1974-08-01 SE SE7409957A patent/SE7409957L/xx unknown
- 1974-08-01 IT IT25881/74A patent/IT1049204B/it active
- 1974-08-01 DK DK410874A patent/DK410874A/da unknown
- 1974-08-02 BE BE1006105A patent/BE818417A/xx unknown
- 1974-08-02 ES ES428914A patent/ES428914A0/es active Pending
- 1974-08-02 PL PL1974192766A patent/PL96805B1/pl unknown
- 1974-08-02 PL PL1974173196A patent/PL91696B1/pl unknown
- 1974-08-02 PL PL1974192765A patent/PL96804B1/pl unknown
- 1974-08-02 FR FR7427017A patent/FR2240009A1/fr active Granted
- 1974-08-02 PL PL1974184214A patent/PL94238B1/pl unknown
- 1974-08-02 PL PL1974184215A patent/PL92429B1/pl unknown
-
1975
- 1975-01-01 AR AR257999A patent/AR205814A1/es active
- 1975-01-01 AR AR258000A patent/AR204130A1/es active
- 1975-09-04 SU SU7502170651A patent/SU565630A3/ru active
- 1975-09-12 SU SU7502171154A patent/SU582758A3/ru active
Also Published As
| Publication number | Publication date |
|---|---|
| BE818417A (fr) | 1975-02-03 |
| AR205814A1 (es) | 1976-06-07 |
| ES428914A0 (es) | 1977-02-01 |
| SU565630A3 (ru) | 1977-07-15 |
| PL92429B1 (enrdf_load_stackoverflow) | 1977-04-30 |
| RO63973A (fr) | 1978-09-15 |
| JPS5047978A (enrdf_load_stackoverflow) | 1975-04-28 |
| AT337691B (de) | 1977-07-11 |
| AR204130A1 (es) | 1975-11-20 |
| DD112759A5 (enrdf_load_stackoverflow) | 1975-05-05 |
| AU7052874A (en) | 1976-01-08 |
| BR7406317D0 (pt) | 1975-05-20 |
| ATA627474A (de) | 1976-11-15 |
| ZA743887B (en) | 1975-06-25 |
| IL45073A0 (en) | 1974-09-10 |
| PL96804B1 (pl) | 1978-01-31 |
| DK410874A (enrdf_load_stackoverflow) | 1975-04-01 |
| SE7409957L (enrdf_load_stackoverflow) | 1975-02-03 |
| PL91696B1 (enrdf_load_stackoverflow) | 1977-03-31 |
| IT1049204B (it) | 1981-01-20 |
| PL94238B1 (enrdf_load_stackoverflow) | 1977-07-30 |
| FR2240009A1 (en) | 1975-03-07 |
| AR203854A1 (es) | 1975-10-31 |
| PL96805B1 (pl) | 1978-01-31 |
| SU582758A3 (ru) | 1977-11-30 |
| FR2240009B1 (enrdf_load_stackoverflow) | 1978-07-28 |
| DE2431775A1 (de) | 1975-02-20 |
| NL7410033A (nl) | 1975-02-04 |
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