JPS596316B2 - 置換イミダゾ〔１，５−ｄ〕−ａｓ−トリアジン−４（３Ｈ）−オン類およびチオン類並にこれらの製造法 - Google Patents
置換イミダゾ〔１，５−ｄ〕−ａｓ−トリアジン−４（３Ｈ）−オン類およびチオン類並にこれらの製造法Info
- Publication number
- JPS596316B2 JPS596316B2 JP53010649A JP1064978A JPS596316B2 JP S596316 B2 JPS596316 B2 JP S596316B2 JP 53010649 A JP53010649 A JP 53010649A JP 1064978 A JP1064978 A JP 1064978A JP S596316 B2 JPS596316 B2 JP S596316B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- hydrogen
- compound
- oxygen
- phenyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 11
- ONOJCVBIBBEBGK-UHFFFAOYSA-N 3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical class OC1=NN=CC2=CN=CN12 ONOJCVBIBBEBGK-UHFFFAOYSA-N 0.000 title description 6
- 241001061127 Thione Species 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 156
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 53
- -1 monosubstituted phenyl Chemical group 0.000 claims description 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 38
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 37
- 239000001301 oxygen Substances 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 25
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 25
- 229910052794 bromium Inorganic materials 0.000 claims description 25
- 239000000460 chlorine Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 20
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 20
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 239000000126 substance Substances 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- 125000005998 bromoethyl group Chemical group 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 239000011630 iodine Substances 0.000 claims description 5
- 239000003960 organic solvent Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 14
- 125000003545 alkoxy group Chemical group 0.000 claims 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 150000001340 alkali metals Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000003944 tolyl group Chemical group 0.000 claims 1
- 238000002844 melting Methods 0.000 description 98
- 230000008018 melting Effects 0.000 description 98
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 67
- 239000000203 mixture Substances 0.000 description 59
- 238000000034 method Methods 0.000 description 55
- 239000007787 solid Substances 0.000 description 55
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- 239000000243 solution Substances 0.000 description 46
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 42
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 35
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- VYSYZMNJHYOXGN-UHFFFAOYSA-N ethyl n-aminocarbamate Chemical compound CCOC(=O)NN VYSYZMNJHYOXGN-UHFFFAOYSA-N 0.000 description 25
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
- 238000002360 preparation method Methods 0.000 description 19
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
- 238000004458 analytical method Methods 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 18
- 238000001953 recrystallisation Methods 0.000 description 18
- 238000003756 stirring Methods 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 15
- 229910017604 nitric acid Inorganic materials 0.000 description 15
- ILAXBOIRSPXAMM-UHFFFAOYSA-N methyl n-aminocarbamodithioate Chemical compound CSC(=S)NN ILAXBOIRSPXAMM-UHFFFAOYSA-N 0.000 description 14
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 12
- 239000002244 precipitate Substances 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 11
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 9
- WFJRIDQGVSJLLH-UHFFFAOYSA-N methyl n-aminocarbamate Chemical compound COC(=O)NN WFJRIDQGVSJLLH-UHFFFAOYSA-N 0.000 description 9
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 8
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical compound CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 7
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 7
- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 238000000354 decomposition reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- 235000011121 sodium hydroxide Nutrition 0.000 description 6
- LFKJFIOTRHYONM-UHFFFAOYSA-N 2-phenyl-1h-imidazole-5-carbaldehyde Chemical compound N1C(C=O)=CN=C1C1=CC=CC=C1 LFKJFIOTRHYONM-UHFFFAOYSA-N 0.000 description 5
- 239000003610 charcoal Substances 0.000 description 5
- RXKJFZQQPQGTFL-UHFFFAOYSA-N dihydroxyacetone Chemical compound OCC(=O)CO RXKJFZQQPQGTFL-UHFFFAOYSA-N 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- RUEBPOOTFCZRBC-UHFFFAOYSA-N (5-methyl-2-phenyl-1h-imidazol-4-yl)methanol Chemical compound OCC1=C(C)NC(C=2C=CC=CC=2)=N1 RUEBPOOTFCZRBC-UHFFFAOYSA-N 0.000 description 4
- RJJUHCRCATVRBK-UHFFFAOYSA-N 2-propyl-1h-imidazole-5-carbaldehyde Chemical compound CCCC1=NC=C(C=O)N1 RJJUHCRCATVRBK-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- QDYTUZCWBJRHKK-UHFFFAOYSA-N imidazole-4-methanol Chemical class OCC1=CNC=N1 QDYTUZCWBJRHKK-UHFFFAOYSA-N 0.000 description 4
- 150000004702 methyl esters Chemical class 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 description 3
- AJAVMTJTPWMHAE-UHFFFAOYSA-N 1h-imidazole;methanol Chemical compound OC.C1=CNC=N1 AJAVMTJTPWMHAE-UHFFFAOYSA-N 0.000 description 3
- QMNWYGTWTXOQTP-UHFFFAOYSA-N 1h-triazin-6-one Chemical compound O=C1C=CN=NN1 QMNWYGTWTXOQTP-UHFFFAOYSA-N 0.000 description 3
- PTHGVOCFAZSNNA-UHFFFAOYSA-N 2-butyl-1h-imidazole-5-carbaldehyde Chemical compound CCCCC1=NC=C(C=O)N1 PTHGVOCFAZSNNA-UHFFFAOYSA-N 0.000 description 3
- QALCPTMLNVUKMD-UHFFFAOYSA-N 5-(dimethoxymethyl)-4-iodo-2-phenyl-1h-imidazole Chemical compound IC1=C(C(OC)OC)NC(C=2C=CC=CC=2)=N1 QALCPTMLNVUKMD-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- GCBSRPOGGYIYGZ-UHFFFAOYSA-N [2-(methoxymethyl)-1h-imidazol-5-yl]methanol Chemical compound COCC1=NC(CO)=CN1 GCBSRPOGGYIYGZ-UHFFFAOYSA-N 0.000 description 3
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- UTDZRAQFRGYPIZ-UHFFFAOYSA-N (1H-imidazol-5-ylmethylideneamino)carbamic acid Chemical class OC(=O)NN=CC1=CNC=N1 UTDZRAQFRGYPIZ-UHFFFAOYSA-N 0.000 description 2
- IRASHGPCCKEGAJ-UHFFFAOYSA-N (1H-imidazol-5-ylmethylideneamino)carbamodithioic acid Chemical compound SC(=S)NN=CC1=CNC=N1 IRASHGPCCKEGAJ-UHFFFAOYSA-N 0.000 description 2
- XMKYXMNRMGDDGL-UHFFFAOYSA-N (2-benzyl-1h-imidazol-5-yl)methanol Chemical compound OCC1=CNC(CC=2C=CC=CC=2)=N1 XMKYXMNRMGDDGL-UHFFFAOYSA-N 0.000 description 2
- GGRBEFVMJHQWFG-UHFFFAOYSA-N (2-phenyl-1h-imidazol-5-yl)methanol Chemical compound OCC1=CNC(C=2C=CC=CC=2)=N1 GGRBEFVMJHQWFG-UHFFFAOYSA-N 0.000 description 2
- RBYFKCAAFQIZAQ-UHFFFAOYSA-N 1h-1,3,5-triazine-2-thione Chemical compound S=C1N=CN=CN1 RBYFKCAAFQIZAQ-UHFFFAOYSA-N 0.000 description 2
- ARDGQYVTLGUJII-UHFFFAOYSA-N 2,2-dimethylpropanimidamide;hydrochloride Chemical compound Cl.CC(C)(C)C(N)=N ARDGQYVTLGUJII-UHFFFAOYSA-N 0.000 description 2
- MFFWADYNIVRMMM-UHFFFAOYSA-N 2,5-dimethyl-1h-imidazole-4-carbaldehyde Chemical compound CC1=NC(C=O)=C(C)N1 MFFWADYNIVRMMM-UHFFFAOYSA-N 0.000 description 2
- QBENGHTZHWANSD-UHFFFAOYSA-N 2-(methoxymethyl)-1h-imidazole-5-carbaldehyde Chemical compound COCC1=NC(C=O)=CN1 QBENGHTZHWANSD-UHFFFAOYSA-N 0.000 description 2
- ZKPDACHGKIGSJV-UHFFFAOYSA-N 2-benzyl-1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC(CC=2C=CC=CC=2)=N1 ZKPDACHGKIGSJV-UHFFFAOYSA-N 0.000 description 2
- URODTOQIGNUZCY-UHFFFAOYSA-N 2-benzyl-5-methyl-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(C)NC(CC=2C=CC=CC=2)=N1 URODTOQIGNUZCY-UHFFFAOYSA-N 0.000 description 2
- ZWULFIBGPXWGFG-UHFFFAOYSA-N 2-methyl-1h-imidazole-5-carbaldehyde Chemical compound CC1=NC=C(C=O)N1 ZWULFIBGPXWGFG-UHFFFAOYSA-N 0.000 description 2
- BSGNHGCLZZKFNY-UHFFFAOYSA-N 2-tert-butyl-1h-imidazole-5-carbaldehyde Chemical compound CC(C)(C)C1=NC(C=O)=CN1 BSGNHGCLZZKFNY-UHFFFAOYSA-N 0.000 description 2
- UETFVEJXNHDCPU-UHFFFAOYSA-N 2-tert-butyl-5-methyl-1h-imidazole-4-carbaldehyde Chemical compound CC=1NC(C(C)(C)C)=NC=1C=O UETFVEJXNHDCPU-UHFFFAOYSA-N 0.000 description 2
- KMWCSNCNHSEXIF-UHFFFAOYSA-N 5-methyl-1h-imidazole-4-carbaldehyde Chemical compound CC=1N=CNC=1C=O KMWCSNCNHSEXIF-UHFFFAOYSA-N 0.000 description 2
- SHEJHKQCPUPVHA-UHFFFAOYSA-N 5-methyl-2-(3-methylphenyl)-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(C)NC(C=2C=C(C)C=CC=2)=N1 SHEJHKQCPUPVHA-UHFFFAOYSA-N 0.000 description 2
- KFVGBCOFGJKBPM-UHFFFAOYSA-N 5-methyl-2-phenyl-1h-imidazole-4-carbaldehyde Chemical compound O=CC1=C(C)NC(C=2C=CC=CC=2)=N1 KFVGBCOFGJKBPM-UHFFFAOYSA-N 0.000 description 2
- MBPOEUWFBVJHPT-UHFFFAOYSA-N 6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound N12C(=O)NN=CC2=CN=C1C1=CC=CC=C1 MBPOEUWFBVJHPT-UHFFFAOYSA-N 0.000 description 2
- GPQDFZOLGWYHJU-UHFFFAOYSA-N 8-bromo-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(Br)N=C2C1=CC=CC=C1 GPQDFZOLGWYHJU-UHFFFAOYSA-N 0.000 description 2
- HUWFSZWQZSGNIM-UHFFFAOYSA-N 8-methyl-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazine-4-thione Chemical compound C1=NNC(=S)N2C1=C(C)N=C2C1=CC=CC=C1 HUWFSZWQZSGNIM-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- VMTQRMVGJPFHDS-UHFFFAOYSA-N [5-methyl-2-(3-methylphenyl)-1h-imidazol-4-yl]methanol Chemical compound OCC1=C(C)NC(C=2C=C(C)C=CC=2)=N1 VMTQRMVGJPFHDS-UHFFFAOYSA-N 0.000 description 2
- 239000002168 alkylating agent Substances 0.000 description 2
- 229940100198 alkylating agent Drugs 0.000 description 2
- 244000309464 bull Species 0.000 description 2
- STYCVEYASXULRN-UHFFFAOYSA-N butanimidamide;hydrochloride Chemical compound [Cl-].CCCC(N)=[NH2+] STYCVEYASXULRN-UHFFFAOYSA-N 0.000 description 2
- OWIUPIRUAQMTTK-UHFFFAOYSA-N carbazic acid Chemical compound NNC(O)=O OWIUPIRUAQMTTK-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- OWUUHEMIBPLJPR-UHFFFAOYSA-N ethyl N-[(2-benzyl-5-methyl-1H-imidazol-4-yl)methylideneamino]carbamate Chemical compound N1C(C)=C(C=NNC(=O)OCC)N=C1CC1=CC=CC=C1 OWUUHEMIBPLJPR-UHFFFAOYSA-N 0.000 description 2
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- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 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
- OTCKOJUMXQWKQG-UHFFFAOYSA-L magnesium bromide Chemical compound [Mg+2].[Br-].[Br-] OTCKOJUMXQWKQG-UHFFFAOYSA-L 0.000 description 1
- 229910001623 magnesium bromide Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- JXRHUEVWIUBPQV-UHFFFAOYSA-N methyl N-(1H-imidazol-5-ylmethylideneamino)carbamodithioate Chemical compound CSC(=S)NN=CC1=CNC=N1 JXRHUEVWIUBPQV-UHFFFAOYSA-N 0.000 description 1
- XAHVHKSDABYTRR-UHFFFAOYSA-N methyl N-[(2-benzyl-5-methyl-1H-imidazol-4-yl)methylideneamino]carbamodithioate Chemical compound N1C(C)=C(C=NNC(=S)SC)N=C1CC1=CC=CC=C1 XAHVHKSDABYTRR-UHFFFAOYSA-N 0.000 description 1
- WSNMWUNFHRYAGM-UHFFFAOYSA-N methyl N-[(2-benzyl-5-propyl-1H-imidazol-4-yl)methylideneamino]carbamodithioate Chemical compound CSC(=S)NN=CC1=C(CCC)NC(CC=2C=CC=CC=2)=N1 WSNMWUNFHRYAGM-UHFFFAOYSA-N 0.000 description 1
- SGRXCTYMFBHRRR-UHFFFAOYSA-N methyl N-[(2-methyl-1H-imidazol-5-yl)methylideneamino]carbamodithioate Chemical compound CSC(=S)NN=CC1=CNC(C)=N1 SGRXCTYMFBHRRR-UHFFFAOYSA-N 0.000 description 1
- NRVFREDCSTUHLY-UHFFFAOYSA-N methyl N-[(2-phenyl-1H-imidazol-5-yl)methylideneamino]carbamodithioate Chemical compound CSC(=S)NN=CC1=CNC(C=2C=CC=CC=2)=N1 NRVFREDCSTUHLY-UHFFFAOYSA-N 0.000 description 1
- VDBWABUVDABAOY-UHFFFAOYSA-N methyl N-[[2-(methoxymethyl)-1H-imidazol-5-yl]methylideneamino]carbamodithioate Chemical compound COCC1=NC(C=NNC(=S)SC)=CN1 VDBWABUVDABAOY-UHFFFAOYSA-N 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- 230000011987 methylation Effects 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
- OWIUPIRUAQMTTK-UHFFFAOYSA-M n-aminocarbamate Chemical compound NNC([O-])=O OWIUPIRUAQMTTK-UHFFFAOYSA-M 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- CXEMWUYNUIKMNF-UHFFFAOYSA-N tert-butyl 4-chlorosulfonylpiperazine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCN(S(Cl)(=O)=O)CC1 CXEMWUYNUIKMNF-UHFFFAOYSA-N 0.000 description 1
- 238000010792 warming 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen 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
- C07D233/68—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76531777A | 1977-02-03 | 1977-02-03 | |
| US76531877A | 1977-02-03 | 1977-02-03 | |
| US84317377A | 1977-10-18 | 1977-10-18 | |
| US05/843,174 US4107307A (en) | 1977-02-03 | 1977-10-18 | Imidazo [1,5-d]-as-triazine-4(3H)-ones and thiones |
| US05/848,836 US4124766A (en) | 1977-02-03 | 1977-11-07 | Substituted 3-(4-imidazolylmethylene)carbazic and thiocarbazic acid esters |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5398994A JPS5398994A (en) | 1978-08-29 |
| JPS596316B2 true JPS596316B2 (ja) | 1984-02-10 |
Family
ID=27542181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP53010649A Expired JPS596316B2 (ja) | 1977-02-03 | 1978-02-03 | 置換イミダゾ〔１，５−ｄ〕−ａｓ−トリアジン−４（３Ｈ）−オン類およびチオン類並にこれらの製造法 |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS596316B2 (de) |
| AR (1) | AR224613A1 (de) |
| BE (1) | BE863567A (de) |
| CA (1) | CA1097638A (de) |
| CH (1) | CH636615A5 (de) |
| DE (1) | DE2804435A1 (de) |
| DK (1) | DK48778A (de) |
| FR (1) | FR2384772A1 (de) |
| GB (1) | GB1597671A (de) |
| GR (1) | GR73810B (de) |
| IE (1) | IE46511B1 (de) |
| IL (1) | IL53783A (de) |
| NL (1) | NL7801230A (de) |
| SE (1) | SE7801270L (de) |
| YU (1) | YU22078A (de) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6337712A (ja) * | 1986-08-01 | 1988-02-18 | Hitachi Ltd | 電界効果トランジスタの保護回路 |
| JPH02185069A (ja) * | 1988-12-02 | 1990-07-19 | Motorola Inc | 高エネルギー阻止能力及び温度補償された阻止電圧を具備する半導体デバイス |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3212749A1 (de) * | 1982-04-06 | 1983-10-13 | Basf Ag, 6700 Ludwigshafen | Neue 5-substituierte 4-methylimidazole und verfahren zu ihrer herstellung |
| DE3302413A1 (de) * | 1983-01-21 | 1984-07-26 | Schering AG, 1000 Berlin und 4709 Bergkamen | Triazinone, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit selektiver herbizider wirkung |
| RU2103262C1 (ru) * | 1992-07-16 | 1998-01-27 | Лонца АГ Гампель/Валлис | Способ получения 2-замещенных 5-хлоримидазол-4-карбальдегидов |
| US5484939A (en) * | 1993-03-12 | 1996-01-16 | Lonza Ltd. | 2-substituted 5-chlorimidazoles |
| US5442075A (en) * | 1993-03-12 | 1995-08-15 | Lonza Ltd. | Process for the production of 2-substituted 5-chlorimidazole-4-carbaldehydes |
| ATE157655T1 (de) * | 1993-03-12 | 1997-09-15 | Lonza Ag | Verfahren zur herstellung von gegebenfalls 2- substituierten 5-chlorimidazolen |
| CA2135541C (en) * | 1993-11-15 | 2006-01-10 | Gareth Griffiths | Process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes |
| CA2175420C (en) * | 1995-05-17 | 2007-04-10 | Gareth Griffiths | Process for the preparation of optionally 2-substituted 5-chloroimidazole-4-carbaldehydes |
| JP4103149B2 (ja) | 1996-01-05 | 2008-06-18 | ロンザ リミテッド | ２−置換５−クロロイミダゾール−４−カルブアルデヒドの製造方法 |
| FR2842809A1 (fr) * | 2002-07-26 | 2004-01-30 | Greenpharma Sas | NOUVELLES PYRAZOLO[1,5-a]-1,3,5-TRIAZINES SUBSTITUEES ET LEURS ANALOGUES, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, UTILISATION A TITRE DE MEDICAMENT ET PROCEDES POUR LEUR PREPARATION |
-
1978
- 1978-01-11 IL IL53783A patent/IL53783A/xx unknown
- 1978-01-13 GR GR55160A patent/GR73810B/el unknown
- 1978-01-16 GB GB1728/78A patent/GB1597671A/en not_active Expired
- 1978-01-23 AR AR270809A patent/AR224613A1/es active
- 1978-01-31 IE IE208/78A patent/IE46511B1/en unknown
- 1978-01-31 YU YU00220/78A patent/YU22078A/xx unknown
- 1978-02-02 DE DE19782804435 patent/DE2804435A1/de not_active Withdrawn
- 1978-02-02 NL NL7801230A patent/NL7801230A/xx not_active Application Discontinuation
- 1978-02-02 BE BE184833A patent/BE863567A/xx not_active IP Right Cessation
- 1978-02-02 CH CH114578A patent/CH636615A5/de not_active IP Right Cessation
- 1978-02-02 DK DK48778A patent/DK48778A/da not_active Application Discontinuation
- 1978-02-02 CA CA296,027A patent/CA1097638A/en not_active Expired
- 1978-02-02 SE SE7801270A patent/SE7801270L/xx unknown
- 1978-02-03 FR FR7803141A patent/FR2384772A1/fr not_active Withdrawn
- 1978-02-03 JP JP53010649A patent/JPS596316B2/ja not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6337712A (ja) * | 1986-08-01 | 1988-02-18 | Hitachi Ltd | 電界効果トランジスタの保護回路 |
| JPH02185069A (ja) * | 1988-12-02 | 1990-07-19 | Motorola Inc | 高エネルギー阻止能力及び温度補償された阻止電圧を具備する半導体デバイス |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2384772A1 (fr) | 1978-10-20 |
| DK48778A (da) | 1978-08-04 |
| YU22078A (en) | 1983-12-31 |
| IL53783A (en) | 1982-08-31 |
| CA1097638A (en) | 1981-03-17 |
| GR73810B (de) | 1984-04-17 |
| JPS5398994A (en) | 1978-08-29 |
| IE46511B1 (en) | 1983-07-13 |
| DE2804435A1 (de) | 1978-08-17 |
| BE863567A (fr) | 1978-08-02 |
| SE7801270L (sv) | 1978-09-29 |
| IE780208L (en) | 1978-08-03 |
| NL7801230A (nl) | 1978-08-07 |
| IL53783A0 (en) | 1978-04-30 |
| AR224613A1 (es) | 1981-12-30 |
| CH636615A5 (en) | 1983-06-15 |
| GB1597671A (en) | 1981-09-09 |
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