CA2157753C - Processes for producing 1-substituted-2-cyanoimidazole compounds - Google Patents
Processes for producing 1-substituted-2-cyanoimidazole compounds Download PDFInfo
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- CA2157753C CA2157753C CA002157753A CA2157753A CA2157753C CA 2157753 C CA2157753 C CA 2157753C CA 002157753 A CA002157753 A CA 002157753A CA 2157753 A CA2157753 A CA 2157753A CA 2157753 C CA2157753 C CA 2157753C
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- 238000000034 method Methods 0.000 title claims abstract description 69
- -1 1-substituted-2-cyanoimidazole compounds Chemical class 0.000 title claims abstract description 47
- 238000006243 chemical reaction Methods 0.000 claims abstract description 137
- 150000001875 compounds Chemical class 0.000 claims abstract description 111
- 239000011541 reaction mixture Substances 0.000 claims abstract description 80
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 claims abstract description 49
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims abstract description 32
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 30
- 239000002253 acid Substances 0.000 claims abstract description 29
- 229910052500 inorganic mineral Inorganic materials 0.000 claims abstract description 29
- 239000011707 mineral Substances 0.000 claims abstract description 29
- 150000003839 salts Chemical class 0.000 claims abstract description 25
- 229940015043 glyoxal Drugs 0.000 claims abstract description 23
- LJHFIVQEAFAURQ-ZPUQHVIOSA-N (NE)-N-[(2E)-2-hydroxyiminoethylidene]hydroxylamine Chemical compound O\N=C\C=N\O LJHFIVQEAFAURQ-ZPUQHVIOSA-N 0.000 claims abstract description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims abstract description 17
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 17
- 239000002585 base Substances 0.000 claims abstract description 15
- 239000002798 polar solvent Substances 0.000 claims abstract description 15
- 238000005849 sulfamoylation reaction Methods 0.000 claims abstract description 15
- 238000006317 isomerization reaction Methods 0.000 claims abstract description 14
- PXJJSXABGXMUSU-UHFFFAOYSA-N disulfur dichloride Chemical compound ClSSCl PXJJSXABGXMUSU-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000004649 carbonic acid derivatives Chemical class 0.000 claims abstract description 9
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims abstract description 8
- HFRXJVQOXRXOPP-UHFFFAOYSA-N thionyl bromide Chemical compound BrS(Br)=O HFRXJVQOXRXOPP-UHFFFAOYSA-N 0.000 claims abstract description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 39
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- 239000002904 solvent Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 21
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical group CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 18
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
- 239000013078 crystal Substances 0.000 description 42
- 235000010755 mineral Nutrition 0.000 description 27
- 238000001914 filtration Methods 0.000 description 24
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 235000011181 potassium carbonates Nutrition 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 238000007792 addition Methods 0.000 description 11
- 150000002460 imidazoles Chemical class 0.000 description 11
- JFCHSQDLLFJHOA-UHFFFAOYSA-N n,n-dimethylsulfamoyl chloride Chemical compound CN(C)S(Cl)(=O)=O JFCHSQDLLFJHOA-UHFFFAOYSA-N 0.000 description 10
- ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 9
- 230000035484 reaction time Effects 0.000 description 9
- UPIAQBGYLUPFBC-UHFFFAOYSA-N 2,2-dichloro-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)C(Cl)Cl)C=C1 UPIAQBGYLUPFBC-UHFFFAOYSA-N 0.000 description 8
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 8
- 238000001816 cooling Methods 0.000 description 8
- QMQZIXCNLUPEIN-UHFFFAOYSA-N 1h-imidazole-2-carbonitrile Chemical class N#CC1=NC=CN1 QMQZIXCNLUPEIN-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
- 229910052794 bromium Inorganic materials 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 239000005457 ice water Substances 0.000 description 7
- 238000007363 ring formation reaction Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- GNKZMNRKLCTJAY-UHFFFAOYSA-N 4'-Methylacetophenone Chemical compound CC(=O)C1=CC=C(C)C=C1 GNKZMNRKLCTJAY-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 description 5
- WOFZZCGLXRAPRP-UHFFFAOYSA-N N-[2-hydroxyimino-1-(4-methylphenyl)ethylidene]hydroxylamine Chemical compound CC1=CC=C(C(C=NO)=NO)C=C1 WOFZZCGLXRAPRP-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- VRXMURDSRPLOGY-UHFFFAOYSA-N n-[2,2-dichloro-1-(4-methylphenyl)ethylidene]hydroxylamine Chemical compound CC1=CC=C(C(=NO)C(Cl)Cl)C=C1 VRXMURDSRPLOGY-UHFFFAOYSA-N 0.000 description 4
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 4
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000001298 alcohols Chemical class 0.000 description 3
- 239000000010 aprotic solvent Substances 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- YXKMMRDKEKCERS-UHFFFAOYSA-N cyazofamid Chemical compound CN(C)S(=O)(=O)N1C(C#N)=NC(Cl)=C1C1=CC=C(C)C=C1 YXKMMRDKEKCERS-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- QBRSFUSGKXVSPM-UHFFFAOYSA-N hydroxylamine;hydrobromide Chemical compound Br.ON QBRSFUSGKXVSPM-UHFFFAOYSA-N 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- 229910052698 phosphorus Inorganic materials 0.000 description 3
- 239000011574 phosphorus Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- LZLOFHDNIIKBIU-UHFFFAOYSA-N 1-(4-bromophenyl)-2,2-dichloroethanone Chemical compound ClC(Cl)C(=O)C1=CC=C(Br)C=C1 LZLOFHDNIIKBIU-UHFFFAOYSA-N 0.000 description 2
- IJHWWJLYZMKEIW-UHFFFAOYSA-N 1-hydroxy-5-(4-methylphenyl)imidazole-2-carbonitrile Chemical compound C1=CC(C)=CC=C1C1=CN=C(C#N)N1O IJHWWJLYZMKEIW-UHFFFAOYSA-N 0.000 description 2
- VBOWXHAZNGCXAV-UHFFFAOYSA-N 2,2-dibromo-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)C(Br)Br)C=C1 VBOWXHAZNGCXAV-UHFFFAOYSA-N 0.000 description 2
- KRVGXFREOJHJAX-UHFFFAOYSA-N 2-bromo-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)CBr)C=C1 KRVGXFREOJHJAX-UHFFFAOYSA-N 0.000 description 2
- HGLJRZYKFVJSEE-UHFFFAOYSA-N 2-chloro-1-(4-methylphenyl)ethanone Chemical compound CC1=CC=C(C(=O)CCl)C=C1 HGLJRZYKFVJSEE-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
- HXGDSTCIQXNYBP-UHFFFAOYSA-N 4-chloro-1-hydroxy-5-(4-methylphenyl)imidazole-2-carbonitrile Chemical compound C1=CC(C)=CC=C1C1=C(Cl)N=C(C#N)N1O HXGDSTCIQXNYBP-UHFFFAOYSA-N 0.000 description 2
- NTPLXRHDUXRPNE-UHFFFAOYSA-N 4-methoxyacetophenone Chemical compound COC1=CC=C(C(C)=O)C=C1 NTPLXRHDUXRPNE-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 235000019253 formic acid Nutrition 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- KNWDPFBEPJMYPF-UHFFFAOYSA-N n-[2,2-dibromo-1-(4-methylphenyl)ethylidene]hydroxylamine Chemical compound CC1=CC=C(C(=NO)C(Br)Br)C=C1 KNWDPFBEPJMYPF-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 235000005985 organic acids Nutrition 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 2
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical compound CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 229910052717 sulfur Inorganic materials 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- MLXJSLOEWNSWKU-BXXMFMFASA-N (NE)-N-[(2E)-2-hydroxyimino-1-phenylethylidene]hydroxylamine Chemical compound [H]\C(=N/O)\C(=N\O)\C1=CC=CC=C1 MLXJSLOEWNSWKU-BXXMFMFASA-N 0.000 description 1
- UXUYADQBOMGCBR-DHZHZOJOSA-N (nz)-n-[2-bromo-1-(4-chlorophenyl)ethylidene]hydroxylamine Chemical compound O\N=C(/CBr)C1=CC=C(Cl)C=C1 UXUYADQBOMGCBR-DHZHZOJOSA-N 0.000 description 1
- WIPDATICDHNWKG-UHFFFAOYSA-N 1,1-dibromo-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(Br)Br WIPDATICDHNWKG-UHFFFAOYSA-N 0.000 description 1
- WUQDQKUJNWIXFE-UHFFFAOYSA-N 1,1-dibromo-3,3-dimethylpentan-2-one Chemical compound CCC(C)(C)C(=O)C(Br)Br WUQDQKUJNWIXFE-UHFFFAOYSA-N 0.000 description 1
- UDWZXMQIEHAAQT-UHFFFAOYSA-N 1,1-dichloro-3,3-dimethylbutan-2-one Chemical compound CC(C)(C)C(=O)C(Cl)Cl UDWZXMQIEHAAQT-UHFFFAOYSA-N 0.000 description 1
- AALTUQGZACRKQR-UHFFFAOYSA-N 1,1-dichloro-3,3-dimethylpentan-2-one Chemical compound CCC(C)(C)C(=O)C(Cl)Cl AALTUQGZACRKQR-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WYECURVXVYPVAT-UHFFFAOYSA-N 1-(4-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Br)C=C1 WYECURVXVYPVAT-UHFFFAOYSA-N 0.000 description 1
- BUZYGTVTZYSBCU-UHFFFAOYSA-N 1-(4-chlorophenyl)ethanone Chemical compound CC(=O)C1=CC=C(Cl)C=C1 BUZYGTVTZYSBCU-UHFFFAOYSA-N 0.000 description 1
- BZOFRNRRMMEHOB-UHFFFAOYSA-N 2,2-dichloro-1-(4-chlorophenyl)ethanone Chemical compound ClC(Cl)C(=O)C1=CC=C(Cl)C=C1 BZOFRNRRMMEHOB-UHFFFAOYSA-N 0.000 description 1
- OBMKWMUEGBPCNK-UHFFFAOYSA-N 2,2-dichloro-1-(4-ethylphenyl)ethanone Chemical compound CCC1=CC=C(C(=O)C(Cl)Cl)C=C1 OBMKWMUEGBPCNK-UHFFFAOYSA-N 0.000 description 1
- YXWSUMDQCTYAOF-UHFFFAOYSA-N 2,2-dichloro-1-(4-methoxyphenyl)ethanone Chemical compound COC1=CC=C(C(=O)C(Cl)Cl)C=C1 YXWSUMDQCTYAOF-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 1
- QSHJLBQLQVSEFV-UHFFFAOYSA-N 3,3-dimethylpentan-2-one Chemical compound CCC(C)(C)C(C)=O QSHJLBQLQVSEFV-UHFFFAOYSA-N 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 125000006275 3-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C([H])C(*)=C1[H] 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004860 4-ethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
- OKSUCCKLAIZTQH-UHFFFAOYSA-N Cl[P] Chemical compound Cl[P] OKSUCCKLAIZTQH-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- JHZADOMLMMVHRB-UHFFFAOYSA-N N-(1-hydroxyimino-3,3-dimethylbutan-2-ylidene)hydroxylamine Chemical compound CC(C)(C)C(=NO)C=NO JHZADOMLMMVHRB-UHFFFAOYSA-N 0.000 description 1
- JSVSGQDUQPZUTP-UHFFFAOYSA-N N-(1-hydroxyimino-3,3-dimethylpentan-2-ylidene)hydroxylamine Chemical compound CCC(C)(C)C(=NO)C=NO JSVSGQDUQPZUTP-UHFFFAOYSA-N 0.000 description 1
- RIRICIQSXKIAPA-UHFFFAOYSA-N N-[1-(4-bromophenyl)-2-hydroxyiminoethylidene]hydroxylamine Chemical compound ON=CC(=NO)C1=CC=C(Br)C=C1 RIRICIQSXKIAPA-UHFFFAOYSA-N 0.000 description 1
- NJOOHWMFLNMYGF-UHFFFAOYSA-N N-[1-(4-chlorophenyl)-2-hydroxyiminoethylidene]hydroxylamine Chemical compound ON=CC(=NO)C1=CC=C(Cl)C=C1 NJOOHWMFLNMYGF-UHFFFAOYSA-N 0.000 description 1
- KLHHKTUTXQGXOV-UHFFFAOYSA-N N-[1-(4-ethylphenyl)-2-hydroxyiminoethylidene]hydroxylamine Chemical compound CCC1=CC=C(C(C=NO)=NO)C=C1 KLHHKTUTXQGXOV-UHFFFAOYSA-N 0.000 description 1
- LKOUDJPVVNGMNS-UHFFFAOYSA-N N-[2-hydroxyimino-1-(4-methoxyphenyl)ethylidene]hydroxylamine Chemical compound COC1=CC=C(C(C=NO)=NO)C=C1 LKOUDJPVVNGMNS-UHFFFAOYSA-N 0.000 description 1
- 206010067482 No adverse event Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- YSVZGWAJIHWNQK-UHFFFAOYSA-N [3-(hydroxymethyl)-2-bicyclo[2.2.1]heptanyl]methanol Chemical compound C1CC2C(CO)C(CO)C1C2 YSVZGWAJIHWNQK-UHFFFAOYSA-N 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 125000002704 decyl 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])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000004817 gas chromatography Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([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
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- SMLBKZLFWPCYAG-UHFFFAOYSA-N n-[2-bromo-1-(4-methylphenyl)ethylidene]hydroxylamine Chemical compound CC1=CC=C(C(CBr)=NO)C=C1 SMLBKZLFWPCYAG-UHFFFAOYSA-N 0.000 description 1
- VJRFTGHBSHYNNA-UHFFFAOYSA-N n-[2-bromo-2-chloro-1-(4-methylphenyl)ethylidene]hydroxylamine Chemical compound CC1=CC=C(C(=NO)C(Cl)Br)C=C1 VJRFTGHBSHYNNA-UHFFFAOYSA-N 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- NODGRWCMFMEGJH-UHFFFAOYSA-N p-ethylacetophenone Chemical compound CCC1=CC=C(C(C)=O)C=C1 NODGRWCMFMEGJH-UHFFFAOYSA-N 0.000 description 1
- PJGSXYOJTGTZAV-UHFFFAOYSA-N pinacolone Chemical compound CC(=O)C(C)(C)C PJGSXYOJTGTZAV-UHFFFAOYSA-N 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 230000002250 progressing effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/32—Oximes
- C07C251/34—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
- C07C251/48—Oximes with oxygen atoms of oxyimino groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with the carbon atom of at least one of the oxyimino groups bound to a carbon atom of a six-membered aromatic ring
-
- 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
- C07C45/63—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 introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- 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
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Steroid Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP24216494 | 1994-09-08 | ||
| JP6-242164 | 1994-09-08 | ||
| JP27032194 | 1994-10-07 | ||
| JP6-270321 | 1994-10-07 | ||
| JP28926794 | 1994-10-28 | ||
| JP6-289267 | 1994-10-28 | ||
| JP7-53629 | 1995-02-16 | ||
| JP5362995 | 1995-02-16 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2157753A1 CA2157753A1 (en) | 1996-03-09 |
| CA2157753C true CA2157753C (en) | 2006-12-12 |
Family
ID=27462936
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002157753A Expired - Fee Related CA2157753C (en) | 1994-09-08 | 1995-09-07 | Processes for producing 1-substituted-2-cyanoimidazole compounds |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US5869683A (enExample) |
| EP (2) | EP0705823A1 (enExample) |
| KR (1) | KR100368510B1 (enExample) |
| AT (1) | ATE187168T1 (enExample) |
| CA (1) | CA2157753C (enExample) |
| DE (1) | DE69513657T2 (enExample) |
| DK (1) | DK0765872T3 (enExample) |
| ES (1) | ES2140778T3 (enExample) |
| GR (1) | GR3032745T3 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7481999B2 (en) * | 1998-05-05 | 2009-01-27 | Adherex Technologies, Inc. | Compounds and methods for modulating OB-cadherin-mediated function |
| US6680175B2 (en) * | 1998-05-05 | 2004-01-20 | Adherex Technologies, Inc. | Methods for diagnosing and evaluating cancer |
| US20050203025A1 (en) * | 1998-05-05 | 2005-09-15 | Adherex Technologies, Inc. | Compounds and methods for modulating nonclassical cadherin-mediated functions |
| WO2000075094A2 (en) * | 1999-06-03 | 2000-12-14 | Ishihara Sangyo Kaisha, Ltd. | Method for producing a halogenated acetophenone |
| AU2003298475A1 (en) * | 2002-11-14 | 2004-06-18 | Adherex Technologies, Inc. | Compounds and methods for modulating desmosomal and atypical cadherin-mediated cell adhesion |
| ITMI20051558A1 (it) | 2005-08-09 | 2007-02-10 | Isagro Spa | Miscele e-o composizioni sinergiche cin elevata attivita'fungicida |
| CA2629295A1 (en) | 2005-11-22 | 2007-05-31 | Ishihara Sangyo Kaisha, Ltd. | Germicide composition for agricultural and gardening applications and method for controlling plant disease |
| CN102424671B (zh) * | 2011-11-04 | 2014-05-14 | 西安近代化学研究所 | 4-氯-2-氰基-1-二甲基氨基磺酰基-5-(4-甲基苯基)咪唑的合成方法 |
| CN103936678B (zh) * | 2014-04-23 | 2016-04-27 | 西安近代化学研究所 | 一种4-氯-2-氰基-n,n-二甲基-5-(4’-甲基苯基)-1h-咪唑-1-磺酰胺的合成方法 |
| CN104292166B (zh) * | 2014-10-14 | 2016-04-27 | 西安近代化学研究所 | 4-氯-2-氰基-n,n-二甲基-5-对甲苯基咪唑-1-磺酰胺合成方法 |
| CN107118160B (zh) * | 2016-12-07 | 2019-06-28 | 盐城辉煌化工有限公司 | 一种2-氰基-4-(对甲苯基)-5-氯-1h-咪唑的制备工艺 |
| JP7142639B2 (ja) | 2017-02-23 | 2022-09-27 | アダマ・マクテシム・リミテッド | ２－シアノイミダゾール化合物の調製方法 |
| CN106986830A (zh) * | 2017-05-11 | 2017-07-28 | 蚌埠中实化学技术有限公司 | 4‑氯‑2‑氰基‑1‑二甲基氨基磺酰基‑5‑(4‑甲基苯基)咪唑的合成方法 |
| CN107602477A (zh) * | 2017-10-25 | 2018-01-19 | 西安近代化学研究所 | 一种氰霜唑原药的精制方法 |
| CN109400534B (zh) * | 2018-10-17 | 2020-11-03 | 兰博尔开封科技有限公司 | 一种1-羟基-4-(4′-甲基苯基)-2-甲肟咪唑-3-氧化物的生产工艺 |
| CN122003401A (zh) * | 2023-09-29 | 2026-05-08 | 克罗普诺赛斯(印度)私人有限公司 | 制备4-氯-5-(4-甲苯基)-1h-咪唑-2-甲腈的方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5219B1 (enExample) | 1968-08-15 | 1977-01-05 | ||
| US4441916A (en) * | 1981-10-19 | 1984-04-10 | Stauffer Chemical Company | Haloalkyloxime herbicidal antidotes |
| CA1339133C (en) | 1987-03-13 | 1997-07-29 | Rikuo Nasu | Imidazole compounds and biocidal composition comprising the same for controlling harmful organisms |
| MY129863A (en) * | 1988-03-11 | 2007-05-31 | Ishihara Sangyo Kaisha | Biocidal composition |
| JP2879164B2 (ja) | 1990-06-28 | 1999-04-05 | 石原産業株式会社 | 置換２―シアノイミダゾール系化合物の製造方法 |
| JPH04120063A (ja) | 1990-09-07 | 1992-04-21 | Ishihara Sangyo Kaisha Ltd | イミダゾール系化合物の分離方法 |
| DE69401486T2 (de) * | 1993-11-12 | 1997-04-30 | Ishihara Sangyo Kaisha | Verfahren zur Herstellung 2-cyanoimidazol Derivate |
-
1995
- 1995-09-06 DE DE69513657T patent/DE69513657T2/de not_active Expired - Lifetime
- 1995-09-06 EP EP95306229A patent/EP0705823A1/en not_active Withdrawn
- 1995-09-06 KR KR1019950029085A patent/KR100368510B1/ko not_active Expired - Lifetime
- 1995-09-06 AT AT96118827T patent/ATE187168T1/de active
- 1995-09-06 DK DK96118827T patent/DK0765872T3/da active
- 1995-09-06 EP EP96118827A patent/EP0765872B1/en not_active Expired - Lifetime
- 1995-09-06 ES ES96118827T patent/ES2140778T3/es not_active Expired - Lifetime
- 1995-09-07 CA CA002157753A patent/CA2157753C/en not_active Expired - Fee Related
-
1997
- 1997-11-03 US US08/962,648 patent/US5869683A/en not_active Expired - Lifetime
-
2000
- 2000-02-23 GR GR20000400445T patent/GR3032745T3/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0765872A2 (en) | 1997-04-02 |
| CA2157753A1 (en) | 1996-03-09 |
| DE69513657D1 (de) | 2000-01-05 |
| ES2140778T3 (es) | 2000-03-01 |
| ATE187168T1 (de) | 1999-12-15 |
| EP0705823A1 (en) | 1996-04-10 |
| DE69513657T2 (de) | 2000-04-06 |
| GR3032745T3 (en) | 2000-06-30 |
| EP0765872A3 (enExample) | 1997-04-09 |
| KR100368510B1 (ko) | 2003-04-23 |
| EP0765872B1 (en) | 1999-12-01 |
| KR960010630A (ko) | 1996-04-20 |
| DK0765872T3 (da) | 2000-05-22 |
| US5869683A (en) | 1999-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20150908 |