NO120369B - - Google Patents
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- Publication number
- NO120369B NO120369B NO170661A NO17066167A NO120369B NO 120369 B NO120369 B NO 120369B NO 170661 A NO170661 A NO 170661A NO 17066167 A NO17066167 A NO 17066167A NO 120369 B NO120369 B NO 120369B
- Authority
- NO
- Norway
- Prior art keywords
- methyl
- nitroimidazole
- thiadiazolyl
- alkyl
- nitro
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 50
- 238000002360 preparation method Methods 0.000 claims description 29
- -1 1-substituted-5-nitro-2-imidazolyl compounds Chemical class 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 238000007363 ring formation reaction Methods 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000007800 oxidant agent Substances 0.000 claims description 3
- YZTJYBJCZXZGCT-UHFFFAOYSA-N phenylpiperazine Chemical group C1CNCCN1C1=CC=CC=C1 YZTJYBJCZXZGCT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052717 sulfur Chemical group 0.000 claims description 3
- 239000011593 sulfur Chemical group 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 42
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 30
- 238000002844 melting Methods 0.000 description 29
- 230000008018 melting Effects 0.000 description 29
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 27
- 239000000243 solution Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000000047 product Substances 0.000 description 22
- 239000007787 solid Substances 0.000 description 21
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 241000287828 Gallus gallus Species 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 15
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 14
- 241000699670 Mus sp. Species 0.000 description 13
- 208000015181 infectious disease Diseases 0.000 description 13
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
- 235000013330 chicken meat Nutrition 0.000 description 12
- WJRXMOFXMJZTJG-UHFFFAOYSA-N 5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazol-2-amine Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2SN(N)NC=2)=N1 WJRXMOFXMJZTJG-UHFFFAOYSA-N 0.000 description 10
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 9
- 238000001953 recrystallisation Methods 0.000 description 9
- 238000000354 decomposition reaction Methods 0.000 description 8
- 239000002244 precipitate Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241001494479 Pecora Species 0.000 description 5
- 241000224527 Trichomonas vaginalis Species 0.000 description 5
- 229960000583 acetic acid Drugs 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 239000012362 glacial acetic acid Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000002243 precursor Substances 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 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 4
- XAKKAVOLKNKDQV-UHFFFAOYSA-N 2-chloro-5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazole Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2SN(Cl)NC=2)=N1 XAKKAVOLKNKDQV-UHFFFAOYSA-N 0.000 description 4
- MKDHCSQJKHOFAH-UHFFFAOYSA-N 5-(1-methyl-5-nitroimidazol-2-yl)-3h-oxadiazol-2-amine Chemical compound C1=C([N+]([O-])=O)N(C)C(C=2ON(N)NC=2)=N1 MKDHCSQJKHOFAH-UHFFFAOYSA-N 0.000 description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 4
- OOIOHEBTXPTBBE-UHFFFAOYSA-N [Na].[Fe] Chemical compound [Na].[Fe] OOIOHEBTXPTBBE-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 125000002883 imidazolyl group Chemical group 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- XCGBKFDCEWLBNP-UHFFFAOYSA-N n-[5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazol-2-yl]acetamide Chemical compound S1N(NC(=O)C)NC=C1C1=NC=C([N+]([O-])=O)N1C XCGBKFDCEWLBNP-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 150000007659 semicarbazones Chemical class 0.000 description 4
- ORLFOTXLOAVEGN-UHFFFAOYSA-N 1,1-dimethyl-3-[(1-methyl-5-nitroimidazol-2-yl)methylideneamino]urea Chemical compound CN(C)C(=O)NN=CC1=NC=C([N+]([O-])=O)N1C ORLFOTXLOAVEGN-UHFFFAOYSA-N 0.000 description 3
- KGPPYSPFURNFNV-UHFFFAOYSA-N 1-methyl-3-[(1-methyl-5-nitroimidazol-2-yl)methylideneamino]urea Chemical compound CNC(=O)NN=CC1=NC=C([N+]([O-])=O)N1C KGPPYSPFURNFNV-UHFFFAOYSA-N 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 3
- 238000009631 Broth culture Methods 0.000 description 3
- 208000004232 Enteritis Diseases 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 208000037386 Typhoid Diseases 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- LCPUDZUWZDSKMX-UHFFFAOYSA-K azane;hydrogen sulfate;iron(3+);sulfate;dodecahydrate Chemical compound [NH4+].O.O.O.O.O.O.O.O.O.O.O.O.[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O LCPUDZUWZDSKMX-UHFFFAOYSA-K 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- BRWIZMBXBAOCCF-UHFFFAOYSA-N hydrazinecarbothioamide Chemical compound NNC(N)=S BRWIZMBXBAOCCF-UHFFFAOYSA-N 0.000 description 3
- 210000003250 oocyst Anatomy 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 244000144977 poultry Species 0.000 description 3
- 235000013594 poultry meat Nutrition 0.000 description 3
- 239000000523 sample Substances 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 210000002784 stomach Anatomy 0.000 description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 3
- SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 3
- 239000001974 tryptic soy broth Substances 0.000 description 3
- 108010050327 trypticase-soy broth Proteins 0.000 description 3
- 201000008297 typhoid fever Diseases 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-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
- 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 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 241000223932 Eimeria tenella Species 0.000 description 2
- 241000588724 Escherichia coli Species 0.000 description 2
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000607142 Salmonella Species 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 241001502500 Trichomonadida Species 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 2
- 229910052921 ammonium sulfate Inorganic materials 0.000 description 2
- 235000011130 ammonium sulphate Nutrition 0.000 description 2
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 2
- 230000001165 anti-coccidial effect Effects 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 210000004027 cell Anatomy 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- IBXPYPUJPLLOIN-UHFFFAOYSA-N dimetridazole Chemical compound CC1=NC=C(N(=O)=O)N1C IBXPYPUJPLLOIN-UHFFFAOYSA-N 0.000 description 2
- 229940042396 direct acting antivirals thiosemicarbazones Drugs 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 description 2
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 2
- VCJMYUPGQJHHFU-UHFFFAOYSA-N iron(3+);trinitrate Chemical compound [Fe+3].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O VCJMYUPGQJHHFU-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 235000010755 mineral Nutrition 0.000 description 2
- 239000011707 mineral Substances 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- YSMITHFGHAQQPE-UHFFFAOYSA-N n-methyl-5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazol-2-amine Chemical compound S1N(NC)NC=C1C1=NC=C([N+]([O-])=O)N1C YSMITHFGHAQQPE-UHFFFAOYSA-N 0.000 description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000012264 purified product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JSAQDPJIVQMBAY-UHFFFAOYSA-N (1-methyl-5-nitroimidazol-2-yl)methanol Chemical compound CN1C(CO)=NC=C1[N+]([O-])=O JSAQDPJIVQMBAY-UHFFFAOYSA-N 0.000 description 1
- RQHMQURGSQBBJY-UHFFFAOYSA-N (2,2-dichloroacetyl) 2,2-dichloroacetate Chemical compound ClC(Cl)C(=O)OC(=O)C(Cl)Cl RQHMQURGSQBBJY-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- SKYYTGUCWARUCL-UHFFFAOYSA-N 1-amino-3-ethylthiourea Chemical compound CCNC(=S)NN SKYYTGUCWARUCL-UHFFFAOYSA-N 0.000 description 1
- LHYKTQVFLKHQSR-UHFFFAOYSA-N 1-amino-3-methylurea Chemical compound CNC(=O)NN LHYKTQVFLKHQSR-UHFFFAOYSA-N 0.000 description 1
- XYNVNGOLNUIHDV-UHFFFAOYSA-N 1-ethyl-2-methyl-5-nitroimidazole Chemical compound CCN1C(C)=NC=C1[N+]([O-])=O XYNVNGOLNUIHDV-UHFFFAOYSA-N 0.000 description 1
- KHANOKKLVMZDGL-UHFFFAOYSA-N 1-ethyl-5-nitroimidazole-2-carbaldehyde Chemical compound CCN1C(C=O)=NC=C1[N+]([O-])=O KHANOKKLVMZDGL-UHFFFAOYSA-N 0.000 description 1
- JLZXSFPSJJMRIX-UHFFFAOYSA-N 1-methyl-5-nitroimidazole Chemical compound CN1C=NC=C1[N+]([O-])=O JLZXSFPSJJMRIX-UHFFFAOYSA-N 0.000 description 1
- XOSGGYZKBFPVBJ-UHFFFAOYSA-N 1-methyl-5-nitroimidazole-2-carbohydrazide Chemical compound CN1C(C(=O)NN)=NC=C1[N+]([O-])=O XOSGGYZKBFPVBJ-UHFFFAOYSA-N 0.000 description 1
- VDZJVXFACHQYKK-UHFFFAOYSA-N 2-(2-formyl-5-nitroimidazol-1-yl)ethyl acetate Chemical compound CC(=O)OCCN1C(C=O)=NC=C1[N+]([O-])=O VDZJVXFACHQYKK-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- VCNCCTOMSFEWBR-UHFFFAOYSA-N 2-[2-(2-acetamido-3h-thiadiazol-5-yl)-5-nitroimidazol-1-yl]ethyl acetate Chemical compound S1N(NC(=O)C)NC=C1C1=NC=C([N+]([O-])=O)N1CCOC(C)=O VCNCCTOMSFEWBR-UHFFFAOYSA-N 0.000 description 1
- XKZTZRVEUZNZBK-UHFFFAOYSA-N 2-[2-(2-amino-3h-thiadiazol-5-yl)-5-nitroimidazol-1-yl]ethanol Chemical compound S1N(N)NC=C1C1=NC=C([N+]([O-])=O)N1CCO XKZTZRVEUZNZBK-UHFFFAOYSA-N 0.000 description 1
- YUPBZDBBIQUHIC-UHFFFAOYSA-N 2-[2-(2-amino-3h-thiadiazol-5-yl)-5-nitroimidazol-1-yl]ethyl acetate Chemical compound CC(=O)OCCN1C([N+]([O-])=O)=CN=C1C1=CNN(N)S1 YUPBZDBBIQUHIC-UHFFFAOYSA-N 0.000 description 1
- KGGXEPGNGMWSAC-UHFFFAOYSA-N 2-[2-(hydroxymethyl)-5-nitroimidazol-1-yl]ethyl acetate Chemical compound CC(=O)OCCN1C(CO)=NC=C1[N+]([O-])=O KGGXEPGNGMWSAC-UHFFFAOYSA-N 0.000 description 1
- PVMUJJKBWLAVHG-UHFFFAOYSA-N 2-[2-[(carbamothioylhydrazinylidene)methyl]-5-nitroimidazol-1-yl]ethyl acetate Chemical compound CC(=O)OCCN1C(C=NNC(N)=S)=NC=C1[N+]([O-])=O PVMUJJKBWLAVHG-UHFFFAOYSA-N 0.000 description 1
- FCPHVJQWZFNNKD-UHFFFAOYSA-N 3-amino-1,1-dimethylthiourea Chemical compound CN(C)C(=S)NN FCPHVJQWZFNNKD-UHFFFAOYSA-N 0.000 description 1
- PGLFGNJUOPLFLV-UHFFFAOYSA-N 3-amino-1,1-dimethylurea Chemical compound CN(C)C(=O)NN PGLFGNJUOPLFLV-UHFFFAOYSA-N 0.000 description 1
- 229940105325 3-dimethylaminopropylamine Drugs 0.000 description 1
- NHFQCVUKJPIWAW-UHFFFAOYSA-N 5-(1-ethyl-5-nitroimidazol-2-yl)-n,n-dimethyl-3h-thiadiazol-2-amine Chemical compound C1=C([N+]([O-])=O)N(CC)C(C=2SN(NC=2)N(C)C)=N1 NHFQCVUKJPIWAW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000003495 Coccidiosis Diseases 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- 206010061126 Escherichia infection Diseases 0.000 description 1
- VTLYFUHAOXGGBS-UHFFFAOYSA-N Fe3+ Chemical class [Fe+3] VTLYFUHAOXGGBS-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 206010023076 Isosporiasis Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241000700159 Rattus Species 0.000 description 1
- 241000220010 Rhode Species 0.000 description 1
- 206010039438 Salmonella Infections Diseases 0.000 description 1
- 241000607132 Salmonella enterica subsp. enterica serovar Gallinarum Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical class [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 241000282898 Sus scrofa Species 0.000 description 1
- AMNOHUABKNGDFS-UHFFFAOYSA-N [(1-methyl-5-nitroimidazol-2-yl)methylideneamino]urea Chemical compound CN1C(C=NNC(N)=O)=NC=C1[N+]([O-])=O AMNOHUABKNGDFS-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 210000004712 air sac Anatomy 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- XGGLLRJQCZROSE-UHFFFAOYSA-K ammonium iron(iii) sulfate Chemical compound [NH4+].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O XGGLLRJQCZROSE-UHFFFAOYSA-K 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000842 anti-protozoal effect Effects 0.000 description 1
- 230000001572 anti-trichomonad Effects 0.000 description 1
- 229940124536 anticoccidial agent Drugs 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- KZTASAUPEDXWMQ-UHFFFAOYSA-N azane;iron(3+) Chemical compound N.[Fe+3] KZTASAUPEDXWMQ-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003224 coccidiostatic agent Substances 0.000 description 1
- ATDGTVJJHBUTRL-UHFFFAOYSA-N cyanogen bromide Chemical compound BrC#N ATDGTVJJHBUTRL-UHFFFAOYSA-N 0.000 description 1
- JUAQRBRHRVLVSV-UHFFFAOYSA-N diazanium sulfate dodecahydrate Chemical compound [NH4+].[NH4+].O.O.O.O.O.O.O.O.O.O.O.O.[O-]S([O-])(=O)=O JUAQRBRHRVLVSV-UHFFFAOYSA-N 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- IUNMPGNGSSIWFP-UHFFFAOYSA-N dimethylaminopropylamine Chemical compound CN(C)CCCN IUNMPGNGSSIWFP-UHFFFAOYSA-N 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003651 drinking water Substances 0.000 description 1
- 235000020188 drinking water Nutrition 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 208000020612 escherichia coli infection Diseases 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- XVEWCEUNSHFUOH-UHFFFAOYSA-N ethyl 4-(aminocarbamothioyl)piperazine-1-carboxylate Chemical compound CCOC(=O)N1CCN(C(=S)NN)CC1 XVEWCEUNSHFUOH-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000004992 fission Effects 0.000 description 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000002198 insoluble material Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 231100000225 lethality Toxicity 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- QSIQWTLTDZEQME-UHFFFAOYSA-N n,n-dimethyl-5-(1-methyl-5-nitroimidazol-2-yl)-3h-oxadiazol-2-amine Chemical compound O1N(N(C)C)NC=C1C1=NC=C([N+]([O-])=O)N1C QSIQWTLTDZEQME-UHFFFAOYSA-N 0.000 description 1
- BZCSBUSMQSIERT-UHFFFAOYSA-N n,n-dimethyl-5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazol-2-amine Chemical compound S1N(N(C)C)NC=C1C1=NC=C([N+]([O-])=O)N1C BZCSBUSMQSIERT-UHFFFAOYSA-N 0.000 description 1
- GWNXVHFBZOQSEW-UHFFFAOYSA-N n-[5-(1-methyl-5-nitroimidazol-2-yl)-3h-oxadiazol-2-yl]acetamide Chemical compound O1N(NC(=O)C)NC=C1C1=NC=C([N+]([O-])=O)N1C GWNXVHFBZOQSEW-UHFFFAOYSA-N 0.000 description 1
- OPZFNXKAFLHYKJ-UHFFFAOYSA-N n-ethyl-5-(1-methyl-5-nitroimidazol-2-yl)-3h-thiadiazol-2-amine Chemical compound S1N(NCC)NC=C1C1=NC=C([N+]([O-])=O)N1C OPZFNXKAFLHYKJ-UHFFFAOYSA-N 0.000 description 1
- LSDCCVHNGPTENC-UHFFFAOYSA-N n-methyl-5-(1-methyl-5-nitroimidazol-2-yl)-3h-oxadiazol-2-amine Chemical compound O1N(NC)NC=C1C1=NC=C([N+]([O-])=O)N1C LSDCCVHNGPTENC-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- WHLAXDUXKMECTM-UHFFFAOYSA-N oxadiazol-4-amine Chemical class NC1=CON=N1 WHLAXDUXKMECTM-UHFFFAOYSA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 238000007243 oxidative cyclization reaction Methods 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- RZEWPBTZTSBBAK-UHFFFAOYSA-J potassium;iron(3+);disulfate Chemical compound [K+].[Fe+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O RZEWPBTZTSBBAK-UHFFFAOYSA-J 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 239000012521 purified sample Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 206010039447 salmonellosis Diseases 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000004317 sodium nitrate Substances 0.000 description 1
- 235000010344 sodium nitrate Nutrition 0.000 description 1
- CRWJEUDFKNYSBX-UHFFFAOYSA-N sodium;hypobromite Chemical compound [Na+].Br[O-] CRWJEUDFKNYSBX-UHFFFAOYSA-N 0.000 description 1
- SAFWHKYSCUAGHQ-UHFFFAOYSA-N sodium;hypoiodite Chemical compound [Na+].I[O-] SAFWHKYSCUAGHQ-UHFFFAOYSA-N 0.000 description 1
- MKBNNYRMBCFUSH-UHFFFAOYSA-J sodium;iron(3+);oxalate Chemical compound [Na+].[Fe+3].[O-]C(=O)C([O-])=O.[O-]C(=O)C([O-])=O MKBNNYRMBCFUSH-UHFFFAOYSA-J 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- CUWHXIJMTMMRTI-UHFFFAOYSA-N thiadiazol-4-amine Chemical class NC1=CSN=N1 CUWHXIJMTMMRTI-UHFFFAOYSA-N 0.000 description 1
- 150000003584 thiosemicarbazones Chemical class 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 150000003722 vitamin derivatives Chemical class 0.000 description 1
- 238000010626 work up procedure 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
-
- 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
-
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60415866A | 1966-12-23 | 1966-12-23 | |
| US65959667A | 1967-08-10 | 1967-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO120369B true NO120369B (fr) | 1970-10-12 |
Family
ID=27084600
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO170661A NO120369B (fr) | 1966-12-23 | 1967-11-22 |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3452035A (fr) |
| BE (1) | BE708528A (fr) |
| DE (1) | DE1670018A1 (fr) |
| ES (2) | ES348599A1 (fr) |
| FR (1) | FR7528M (fr) |
| GB (1) | GB1204699A (fr) |
| GR (1) | GR35178B (fr) |
| IL (1) | IL29034A (fr) |
| NL (1) | NL6717685A (fr) |
| NO (1) | NO120369B (fr) |
| SE (1) | SE328894B (fr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3991200A (en) * | 1974-04-25 | 1976-11-09 | American Cyanamid Company | Substituted nitroimidazolyl thiadiazoles and oxadiazoles as antibacterial agents and growth promoting compounds |
| US4065567A (en) * | 1966-12-23 | 1977-12-27 | American Cyanamid Company | Substituted nitroimidazolyl thiadiazoles and oxadiazoles as antibacterial agents and growth promoting compounds |
| US3904756A (en) * | 1966-12-23 | 1975-09-09 | American Cyanamid Co | Substituted nitroimidazolyl thiadiazoles and oxadiazoles as antibacterial agents and growth promoting compounds |
| US3711495A (en) * | 1970-01-07 | 1973-01-16 | Merck & Co Inc | Isoxazalin-3-yl-substituted-5-nitroimidazoles |
| US4058617A (en) * | 1972-10-04 | 1977-11-15 | Ciba-Geigy Corporation | Imidazoles and pharmaceutical composition |
| US3980794A (en) * | 1974-05-13 | 1976-09-14 | Eli Lilly And Company | Method for promoting growth of poultry with 3-(5-nitro-2-imidazolyl)pyrazoles |
| EP0000452B1 (fr) * | 1977-07-12 | 1981-05-06 | Synthelabo | Dérivés d'oxadiazole-1,2,4, leur préparation et leur application en thérapeutique. |
| US7354944B2 (en) * | 2004-10-18 | 2008-04-08 | Amgen Inc. | Thiadiazole compounds and methods of use |
| WO2009011871A2 (fr) * | 2007-07-17 | 2009-01-22 | Amgen Inc. | Thiadiazoles modulateurs de l'activité de pkb |
| CA2692713A1 (fr) | 2007-07-17 | 2009-01-22 | Amgen Inc. | Modulateurs heterocycliques de pkb |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3025303A (en) * | 1957-09-30 | 1962-03-13 | Pharmacia Ab | Certain nitrofuryl, thiadiazolyl amines |
-
1967
- 1967-08-10 US US659596A patent/US3452035A/en not_active Expired - Lifetime
- 1967-11-22 NO NO170661A patent/NO120369B/no unknown
- 1967-11-23 GR GR670135178A patent/GR35178B/el unknown
- 1967-11-29 IL IL29034A patent/IL29034A/en unknown
- 1967-11-30 GB GB54654/67A patent/GB1204699A/en not_active Expired
- 1967-12-20 FR FR133070A patent/FR7528M/fr not_active Expired
- 1967-12-21 SE SE17613/67A patent/SE328894B/xx unknown
- 1967-12-23 DE DE19671670018 patent/DE1670018A1/de active Pending
- 1967-12-23 ES ES348599A patent/ES348599A1/es not_active Expired
- 1967-12-27 BE BE708528D patent/BE708528A/xx unknown
- 1967-12-27 NL NL6717685A patent/NL6717685A/xx unknown
-
1968
- 1968-10-30 ES ES359720A patent/ES359720A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6717685A (fr) | 1968-06-24 |
| FR7528M (fr) | 1969-12-22 |
| US3452035A (en) | 1969-06-24 |
| SE328894B (fr) | 1970-09-28 |
| DE1670018A1 (de) | 1971-01-21 |
| GR35178B (el) | 1968-08-22 |
| BE708528A (fr) | 1968-06-27 |
| ES348599A1 (es) | 1969-06-16 |
| GB1204699A (en) | 1970-09-09 |
| ES359720A1 (es) | 1970-09-16 |
| IL29034A (en) | 1972-05-30 |
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