DD249477A5 - Substituierte 2-phenyl-hexahydro-1,2,4-triazin-3,5-dione, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung - Google Patents
Substituierte 2-phenyl-hexahydro-1,2,4-triazin-3,5-dione, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung Download PDFInfo
- Publication number
- DD249477A5 DD249477A5 DD86294182A DD29418286A DD249477A5 DD 249477 A5 DD249477 A5 DD 249477A5 DD 86294182 A DD86294182 A DD 86294182A DD 29418286 A DD29418286 A DD 29418286A DD 249477 A5 DD249477 A5 DD 249477A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- alkyl
- atoms
- hydrogen
- substituted
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 14
- HUQXVCMANCHPAD-UHFFFAOYSA-N 2-phenyl-1,2,4-triazinane-3,5-dione Chemical class O=C1NC(=O)CNN1C1=CC=CC=C1 HUQXVCMANCHPAD-UHFFFAOYSA-N 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 benzylsulfinyl Chemical group 0.000 claims abstract description 41
- 150000001875 compounds Chemical class 0.000 claims abstract description 40
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 16
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 8
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims abstract description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 6
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 5
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 4
- 125000004442 acylamino group Chemical group 0.000 claims abstract description 3
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims abstract description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 3
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 28
- 239000001257 hydrogen Substances 0.000 claims description 28
- 239000000460 chlorine Substances 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 11
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- ZVIOKRWHGOILAU-UHFFFAOYSA-N 1,2,4-triazinane-3,5-dione Chemical class O=C1CNNC(=O)N1 ZVIOKRWHGOILAU-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 3
- 125000006177 alkyl benzyl group Chemical group 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N N-phenyl amine Natural products NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- KHUXNRRPPZOJPT-UHFFFAOYSA-N phenoxy radical Chemical class O=C1C=C[CH]C=C1 KHUXNRRPPZOJPT-UHFFFAOYSA-N 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims 1
- 230000029936 alkylation Effects 0.000 abstract description 6
- 238000005804 alkylation reaction Methods 0.000 abstract description 6
- 230000010933 acylation Effects 0.000 abstract description 4
- 238000005917 acylation reaction Methods 0.000 abstract description 4
- 230000002192 coccidiostatic effect Effects 0.000 abstract description 4
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 abstract 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 208000003495 Coccidiosis Diseases 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 206010023076 Isosporiasis Diseases 0.000 description 7
- 229960000583 acetic acid Drugs 0.000 description 7
- 239000012362 glacial acetic acid Substances 0.000 description 7
- 150000002431 hydrogen Chemical class 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000012312 sodium hydride Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- QPSUMTKATGFDON-UHFFFAOYSA-N 2-[3,5-dichloro-4-(4-methylsulfonylphenoxy)phenyl]-1,2,4-triazinane-3,5-dione Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1=C(Cl)C=C(N2C(NC(=O)CN2)=O)C=C1Cl QPSUMTKATGFDON-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 241001465754 Metazoa Species 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003224 coccidiostatic agent Substances 0.000 description 4
- 239000003814 drug Substances 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- LRSIWCGUFUUZIA-UHFFFAOYSA-N 2-[3,5-dichloro-4-(4-methylphenyl)sulfanylphenyl]-1-methyl-1,2,4-triazinane-3,5-dione Chemical compound ClC=1C=C(C=C(C=1SC1=CC=C(C=C1)C)Cl)N1N(CC(NC1=O)=O)C LRSIWCGUFUUZIA-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 3
- 238000006722 reduction reaction Methods 0.000 description 3
- 235000011150 stannous chloride Nutrition 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- 241000224483 Coccidia Species 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000223932 Eimeria tenella Species 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000012876 carrier material Substances 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 239000003651 drinking water Substances 0.000 description 2
- 235000020188 drinking water Nutrition 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 210000003250 oocyst Anatomy 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000001119 stannous chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HHVIBTZHLRERCL-UHFFFAOYSA-N sulfonyldimethane Chemical compound CS(C)(=O)=O HHVIBTZHLRERCL-UHFFFAOYSA-N 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NPNKTBZVRIIPQC-UHFFFAOYSA-N 1-acetyl-2-[3,5-dichloro-4-(4-methylsulfonylphenoxy)phenyl]-1,2,4-triazinane-3,5-dione Chemical compound CC(=O)N1CC(=O)NC(=O)N1C(C=C1Cl)=CC(Cl)=C1OC1=CC=C(S(C)(=O)=O)C=C1 NPNKTBZVRIIPQC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- KVMXNOZLNWXYNS-UHFFFAOYSA-N 2-[3,5-dichloro-4-(4-methylphenyl)sulfanylphenyl]-1,2,4-triazinane-3,5-dione Chemical compound C1=CC(C)=CC=C1SC1=C(Cl)C=C(N2C(NC(=O)CN2)=O)C=C1Cl KVMXNOZLNWXYNS-UHFFFAOYSA-N 0.000 description 1
- HDVRGTYTWDKBLL-UHFFFAOYSA-N 2-[3,5-dichloro-4-(4-methylphenyl)sulfanylphenyl]-1,4-dimethyl-1,2,4-triazinane-3,5-dione Chemical compound ClC=1C=C(C=C(C1SC1=CC=C(C=C1)C)Cl)N1N(CC(N(C1=O)C)=O)C HDVRGTYTWDKBLL-UHFFFAOYSA-N 0.000 description 1
- GDXKDHHBEAFWJM-UHFFFAOYSA-N 2-[3,5-dichloro-4-(4-methylphenyl)sulfanylphenyl]-3,5-dioxo-1,2,4-triazinane-1-carbaldehyde Chemical compound ClC=1C=C(C=C(C=1SC1=CC=C(C=C1)C)Cl)N1N(CC(NC1=O)=O)C=O GDXKDHHBEAFWJM-UHFFFAOYSA-N 0.000 description 1
- AQAZEGOUFUGKBP-UHFFFAOYSA-N 2-[3,5-dichloro-4-(4-methylsulfonylphenoxy)phenyl]-1-methyl-1,2,4-triazinane-3,5-dione Chemical compound CN1CC(=O)NC(=O)N1C(C=C1Cl)=CC(Cl)=C1OC1=CC=C(S(C)(=O)=O)C=C1 AQAZEGOUFUGKBP-UHFFFAOYSA-N 0.000 description 1
- PBHVFUOWBSGUTH-UHFFFAOYSA-N 2-[3,5-dichloro-4-(4-methylsulfonylphenoxy)phenyl]-3,5-dioxo-1,2,4-triazinane-1-carbaldehyde Chemical compound C1=CC(S(=O)(=O)C)=CC=C1OC1=C(Cl)C=C(N2C(NC(=O)CN2C=O)=O)C=C1Cl PBHVFUOWBSGUTH-UHFFFAOYSA-N 0.000 description 1
- SDMZBLFBDJUYAH-UHFFFAOYSA-N 2-[3,5-dichloro-4-(4-methylsulfonylphenoxy)phenyl]-4-methyl-1,2,4-triazinane-3,5-dione Chemical compound O=C1N(C)C(=O)CNN1C(C=C1Cl)=CC(Cl)=C1OC1=CC=C(S(C)(=O)=O)C=C1 SDMZBLFBDJUYAH-UHFFFAOYSA-N 0.000 description 1
- 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 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- 206010028400 Mutagenic effect Diseases 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 239000007868 Raney catalyst Substances 0.000 description 1
- 229910000564 Raney nickel Inorganic materials 0.000 description 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 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
- 239000002253 acid Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical compound O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 description 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 230000002152 alkylating effect Effects 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000002246 antineoplastic agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 229940127089 cytotoxic agent Drugs 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- DPOPJTBOMCSYAQ-UHFFFAOYSA-N ethyl n-[3-(ethoxycarbonylamino)-3-oxopropanoyl]carbamate Chemical compound CCOC(=O)NC(=O)CC(=O)NC(=O)OCC DPOPJTBOMCSYAQ-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000003304 gavage Methods 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 230000003903 intestinal lesions Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- MJGFBOZCAJSGQW-UHFFFAOYSA-N mercury sodium Chemical compound [Na].[Hg] MJGFBOZCAJSGQW-UHFFFAOYSA-N 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 231100000243 mutagenic effect Toxicity 0.000 description 1
- 230000003505 mutagenic effect Effects 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 238000009374 poultry farming Methods 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 229910001023 sodium amalgam Inorganic materials 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- AXZWODMDQAVCJE-UHFFFAOYSA-L tin(II) chloride (anhydrous) Chemical compound [Cl-].[Cl-].[Sn+2] AXZWODMDQAVCJE-UHFFFAOYSA-L 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Fodder In General (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Seasonings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Immobilizing And Processing Of Enzymes And Microorganisms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19853531919 DE3531919A1 (de) | 1985-09-07 | 1985-09-07 | Substituierte 2-phenyl-hexahydro-1,2,4-triazin-3,5-dione, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD249477A5 true DD249477A5 (de) | 1987-09-09 |
Family
ID=6280327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD86294182A DD249477A5 (de) | 1985-09-07 | 1986-09-05 | Substituierte 2-phenyl-hexahydro-1,2,4-triazin-3,5-dione, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US4782056A (cs) |
| EP (1) | EP0215354B1 (cs) |
| JP (1) | JPS6261972A (cs) |
| KR (1) | KR940001729B1 (cs) |
| AT (1) | ATE62901T1 (cs) |
| AU (1) | AU588052B2 (cs) |
| BG (1) | BG45552A3 (cs) |
| CA (1) | CA1290332C (cs) |
| CS (1) | CS258144B2 (cs) |
| DD (1) | DD249477A5 (cs) |
| DE (2) | DE3531919A1 (cs) |
| DK (1) | DK167395B1 (cs) |
| ES (1) | ES2001292A6 (cs) |
| HU (1) | HU196594B (cs) |
| IL (1) | IL79951A0 (cs) |
| NZ (1) | NZ217471A (cs) |
| PH (1) | PH22566A (cs) |
| PL (1) | PL147476B1 (cs) |
| PT (1) | PT83306B (cs) |
| SU (1) | SU1517760A3 (cs) |
| ZA (1) | ZA866756B (cs) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU196892B (en) * | 1984-06-12 | 1989-02-28 | Fmc Corp | Herbicides containing as active substance derivatives of 2-phenil-1,2,4-triasine-3,5-dion and process for production of these derivatives |
| DE3814323A1 (de) * | 1988-04-28 | 1989-11-09 | Hoechst Ag | Wasserloesliche zubereitungen von coccidiostatica |
| GB8810185D0 (en) * | 1988-04-29 | 1988-06-02 | Glaxo Group Ltd | Chemical compounds |
| CN1044905A (zh) * | 1989-02-16 | 1990-08-29 | 赫彻斯特股份公司 | 鱼和昆虫寄生虫对抗剂 |
| CA2012004A1 (en) * | 1989-03-15 | 1990-09-15 | Frank Ellis | Chemical compounds |
| DE4030042A1 (de) * | 1990-05-17 | 1991-11-21 | Bayer Ag | Verwendung von substituierten 1,2,4-triazindionen |
| EP0476439A1 (de) * | 1990-09-18 | 1992-03-25 | Bayer Ag | Substituierte 1,2,4-Triazindione, Verfahren zu ihrer Herstellung, Zwischenprodukte dafür und ihre Verwendung |
| DE4120138A1 (de) * | 1991-06-19 | 1992-12-24 | Bayer Ag | Substituierte hexahydro-1,2,4-triazindione, verfahren zu ihrer herstellung, zwischenprodukte dafuer und ihre verwendung |
| US5994355A (en) * | 1993-10-15 | 1999-11-30 | Takeda Chemical Industries, Ltd. | 1, 2, 4-Triazin-3-one derivatives, production and use thereof |
| US5436243A (en) * | 1993-11-17 | 1995-07-25 | Research Triangle Institute Duke University | Aminoanthraquinone derivatives to combat multidrug resistance |
| EP0831088B1 (en) * | 1996-08-30 | 2002-11-27 | Takeda Schering-Plough Animal Health K.K. | 1,2,4-Triazine-3,5-dione derivatives as anticoccidial agents |
| AU8885498A (en) | 1997-08-29 | 1999-03-22 | Takeda Chemical Industries Ltd. | Triazine derivatives, their production and use |
| EA020460B1 (ru) | 2009-01-12 | 2014-11-28 | Пфайзер Лимитед | Производные сульфонамида |
| ES2532356T3 (es) | 2010-07-09 | 2015-03-26 | Pfizer Limited | N-sulfonilbenzamidas como inhibidores de los canales de sodio dependientes de voltaje |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2149645A1 (de) * | 1970-10-07 | 1972-09-14 | Pfizer | 2-Phenyl-as-triazin-3.5-(2H,4H)-dione und die Verwendung dieser Verbindungen zur Bekaempfung der Coccidiose |
| GB1448696A (en) * | 1973-05-29 | 1976-09-08 | Pfizer | 2-phqnyl-astriazine-3,4-2h,4h-diones |
| DE2722537A1 (de) * | 1977-05-18 | 1978-11-23 | Hoechst Ag | Substituierte 2-phenyl-1,2,4-triazin-3,5-(2h,4h)-dione, verfahren zu ihrer herstellung und sie enthaltende coccidiostatische mittel |
| IL62151A (en) * | 1981-02-18 | 1984-10-31 | Abic B M | Hexahydro-1,2,4-triazine-3,5-dione derivatives,their preparation and feed compositions,drinking water and pharmaceutical compositions containing said derivatives |
| DE3408924A1 (de) * | 1984-03-12 | 1985-09-26 | Hoechst Ag, 6230 Frankfurt | Substituierte 2-phenyl-hexahydro-1,2,4-triazin-3,5-dione, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung |
| CA1244024A (en) * | 1984-08-01 | 1988-11-01 | Gustaaf M. Boeckx | .alpha.- ARYL-4-(4,5-DIHYDRO-3,5-DIOXO-1,2,4-TRIAZIN- 2(3H)-YL)BENZENEACETONITRILES |
-
1985
- 1985-09-07 DE DE19853531919 patent/DE3531919A1/de not_active Withdrawn
-
1986
- 1986-08-28 AT AT86111924T patent/ATE62901T1/de not_active IP Right Cessation
- 1986-08-28 DE DE8686111924T patent/DE3678884D1/de not_active Expired - Fee Related
- 1986-08-28 EP EP86111924A patent/EP0215354B1/de not_active Expired - Lifetime
- 1986-09-02 BG BG076342A patent/BG45552A3/xx unknown
- 1986-09-04 PT PT83306A patent/PT83306B/pt not_active IP Right Cessation
- 1986-09-04 CS CS866428A patent/CS258144B2/cs unknown
- 1986-09-05 NZ NZ217471A patent/NZ217471A/xx unknown
- 1986-09-05 IL IL79951A patent/IL79951A0/xx not_active IP Right Cessation
- 1986-09-05 PL PL1986261303A patent/PL147476B1/pl unknown
- 1986-09-05 SU SU864028140A patent/SU1517760A3/ru active
- 1986-09-05 DK DK425486A patent/DK167395B1/da not_active IP Right Cessation
- 1986-09-05 US US06/903,752 patent/US4782056A/en not_active Expired - Fee Related
- 1986-09-05 JP JP61208110A patent/JPS6261972A/ja active Pending
- 1986-09-05 ZA ZA866756A patent/ZA866756B/xx unknown
- 1986-09-05 CA CA000517636A patent/CA1290332C/en not_active Expired - Fee Related
- 1986-09-05 PH PH34225A patent/PH22566A/en unknown
- 1986-09-05 DD DD86294182A patent/DD249477A5/de not_active IP Right Cessation
- 1986-09-05 HU HU863863A patent/HU196594B/hu not_active IP Right Cessation
- 1986-09-05 ES ES8601669A patent/ES2001292A6/es not_active Expired
- 1986-09-05 AU AU62368/86A patent/AU588052B2/en not_active Ceased
- 1986-09-06 KR KR1019860007475A patent/KR940001729B1/ko not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| PH22566A (en) | 1988-10-17 |
| NZ217471A (en) | 1989-06-28 |
| EP0215354A3 (en) | 1989-01-18 |
| DK425486D0 (da) | 1986-09-05 |
| IL79951A0 (en) | 1986-12-31 |
| CS258144B2 (en) | 1988-07-15 |
| JPS6261972A (ja) | 1987-03-18 |
| CA1290332C (en) | 1991-10-08 |
| ES2001292A6 (es) | 1988-05-01 |
| DE3678884D1 (de) | 1991-05-29 |
| AU588052B2 (en) | 1989-09-07 |
| PL147476B1 (en) | 1989-06-30 |
| EP0215354A2 (de) | 1987-03-25 |
| ATE62901T1 (de) | 1991-05-15 |
| KR940001729B1 (ko) | 1994-03-05 |
| PT83306B (pt) | 1989-05-12 |
| DE3531919A1 (de) | 1987-03-19 |
| PT83306A (de) | 1986-10-01 |
| US4782056A (en) | 1988-11-01 |
| PL261303A1 (en) | 1988-03-17 |
| HU196594B (en) | 1988-12-28 |
| DK167395B1 (da) | 1993-10-25 |
| ZA866756B (en) | 1987-04-29 |
| EP0215354B1 (de) | 1991-04-24 |
| KR870003077A (ko) | 1987-04-15 |
| HUT45031A (en) | 1988-05-30 |
| AU6236886A (en) | 1987-03-12 |
| CS642886A2 (en) | 1987-11-12 |
| BG45552A3 (bg) | 1989-06-15 |
| SU1517760A3 (ru) | 1989-10-23 |
| DK425486A (da) | 1987-03-08 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ENJ | Ceased due to non-payment of renewal fee |