DE2932305A1 - Azolo- eckige klammer auf 5,1-d eckige klammer zu - eckige klammer auf 1,2,3,5 eckige klammer zu -tetrazin-4-one und verfahren zur herstellung dieser verbindungen - Google Patents
Azolo- eckige klammer auf 5,1-d eckige klammer zu - eckige klammer auf 1,2,3,5 eckige klammer zu -tetrazin-4-one und verfahren zur herstellung dieser verbindungenInfo
- Publication number
- DE2932305A1 DE2932305A1 DE19792932305 DE2932305A DE2932305A1 DE 2932305 A1 DE2932305 A1 DE 2932305A1 DE 19792932305 DE19792932305 DE 19792932305 DE 2932305 A DE2932305 A DE 2932305A DE 2932305 A1 DE2932305 A1 DE 2932305A1
- Authority
- DE
- Germany
- Prior art keywords
- alkyl
- formula
- phenyl
- isocyanate
- methyl
- 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.)
- Granted
Links
- 239000012948 isocyanate Substances 0.000 title claims description 14
- QLSWIGRIBOSFMV-UHFFFAOYSA-N 1h-pyrrol-2-amine Chemical compound NC1=CC=CN1 QLSWIGRIBOSFMV-UHFFFAOYSA-N 0.000 title claims description 9
- 150000002513 isocyanates Chemical class 0.000 title claims description 7
- 238000006243 chemical reaction Methods 0.000 title description 4
- -1 benxyl Chemical group 0.000 claims abstract description 28
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 14
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 14
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 12
- 150000002367 halogens Chemical class 0.000 claims abstract description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 9
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 9
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
- 125000003118 aryl group Chemical group 0.000 claims abstract description 4
- 125000005359 phenoxyalkyl group Chemical group 0.000 claims abstract description 4
- 125000005504 styryl group Chemical group 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 125000005442 diisocyanate group Chemical group 0.000 claims description 5
- 125000006539 C12 alkyl 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])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 abstract description 5
- 239000000975 dye Substances 0.000 abstract description 4
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical group C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 abstract description 2
- 239000000543 intermediate Substances 0.000 abstract description 2
- 229940125723 sedative agent Drugs 0.000 abstract description 2
- 239000000932 sedative agent Substances 0.000 abstract description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 abstract 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical group C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 abstract 1
- 230000001754 anti-pyretic effect Effects 0.000 abstract 1
- 239000002221 antipyretic Substances 0.000 abstract 1
- 229940125716 antipyretic agent Drugs 0.000 abstract 1
- CZZYITDELCSZES-UHFFFAOYSA-N diphenylmethane Chemical group C=1C=CC=CC=1CC1=CC=CC=C1 CZZYITDELCSZES-UHFFFAOYSA-N 0.000 abstract 1
- 239000000417 fungicide Substances 0.000 abstract 1
- 239000004009 herbicide Substances 0.000 abstract 1
- 239000005648 plant growth regulator Substances 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000243 solution Substances 0.000 description 26
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 14
- 238000003756 stirring Methods 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 229910052739 hydrogen Inorganic materials 0.000 description 10
- 239000001257 hydrogen Substances 0.000 description 10
- 239000013078 crystal Substances 0.000 description 9
- 238000001816 cooling Methods 0.000 description 7
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 7
- 235000010288 sodium nitrite Nutrition 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000007858 starting material Substances 0.000 description 6
- UMDNRKCXSUJMCY-UHFFFAOYSA-N 5-methyl-4-phenyl-1h-pyrazol-3-amine Chemical compound N1N=C(N)C(C=2C=CC=CC=2)=C1C UMDNRKCXSUJMCY-UHFFFAOYSA-N 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 238000001704 evaporation Methods 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 239000011737 fluorine Substances 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- FMDGXCSMDZMDHZ-UHFFFAOYSA-N 1-isocyanato-4-methoxybenzene Chemical compound COC1=CC=C(N=C=O)C=C1 FMDGXCSMDZMDHZ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 229920002554 vinyl polymer Polymers 0.000 description 3
- ADAKRBAJFHTIEW-UHFFFAOYSA-N 1-chloro-4-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C=C1 ADAKRBAJFHTIEW-UHFFFAOYSA-N 0.000 description 2
- GFNKTLQTQSALEJ-UHFFFAOYSA-N 1-isocyanato-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(N=C=O)C=C1 GFNKTLQTQSALEJ-UHFFFAOYSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- VFRADINKOCDNSG-UHFFFAOYSA-N 5-phenyl-2h-triazol-4-amine Chemical compound N1N=NC(C=2C=CC=CC=2)=C1N VFRADINKOCDNSG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000001632 sodium acetate Substances 0.000 description 2
- 235000017281 sodium acetate Nutrition 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- 235000017550 sodium carbonate Nutrition 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZFXBERJDEUDDMX-UHFFFAOYSA-N 1,2,3,5-tetrazine Chemical class C1=NC=NN=N1 ZFXBERJDEUDDMX-UHFFFAOYSA-N 0.000 description 1
- LNKSOGFDOODVSP-UHFFFAOYSA-N 1,3-diisocyanato-2-methylbenzene;2,4-diisocyanato-1-methylbenzene Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O.CC1=C(N=C=O)C=CC=C1N=C=O LNKSOGFDOODVSP-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- APLTYWUNDZWMGC-UHFFFAOYSA-N 1,4-diisocyanatobutane;1,6-diisocyanatohexane;1,5-diisocyanatopentane Chemical compound O=C=NCCCCN=C=O.O=C=NCCCCCN=C=O.O=C=NCCCCCCN=C=O APLTYWUNDZWMGC-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- JJSCUXAFAJEQGB-UHFFFAOYSA-N 1-isocyanatoethylbenzene Chemical compound O=C=NC(C)C1=CC=CC=C1 JJSCUXAFAJEQGB-UHFFFAOYSA-N 0.000 description 1
- SDECTRZHYVCDFI-UHFFFAOYSA-N 1h-indazol-3-amine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=CC=C2C(N)=NNC2=C1 SDECTRZHYVCDFI-UHFFFAOYSA-N 0.000 description 1
- JVVRJMXHNUAPHW-UHFFFAOYSA-N 1h-pyrazol-5-amine Chemical compound NC=1C=CNN=1 JVVRJMXHNUAPHW-UHFFFAOYSA-N 0.000 description 1
- DWMVAKOYQFTJRB-UHFFFAOYSA-N 1h-pyrrole-2-diazonium Chemical class N#[N+]C1=CC=CN1 DWMVAKOYQFTJRB-UHFFFAOYSA-N 0.000 description 1
- BDZHCMDWAXSQMS-UHFFFAOYSA-N 1h-pyrrolo[2,1-d][1,2,3,5]tetrazin-4-one Chemical class O=C1NN=NC2=CC=CN12 BDZHCMDWAXSQMS-UHFFFAOYSA-N 0.000 description 1
- ZXFWQRRQKYBTQV-UHFFFAOYSA-N 2-diazopyrrole Chemical class [N-]=[N+]=C1C=CC=N1 ZXFWQRRQKYBTQV-UHFFFAOYSA-N 0.000 description 1
- KVPFYVXFTCZQIZ-UHFFFAOYSA-N 3,8-diphenyltriazolo[5,1-d][1,2,3,5]tetrazin-4-one Chemical compound C1(=CC=CC=C1)N1N=NC=2N(C1=O)N=NC=2C1=CC=CC=C1 KVPFYVXFTCZQIZ-UHFFFAOYSA-N 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- XYUCWPGMJLLNRT-UHFFFAOYSA-N 4-diazotriazole Chemical compound [N-]=[N+]=C1C=NN=N1 XYUCWPGMJLLNRT-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- MGYGFNQQGAQEON-UHFFFAOYSA-N 4-tolyl isocyanate Chemical compound CC1=CC=C(N=C=O)C=C1 MGYGFNQQGAQEON-UHFFFAOYSA-N 0.000 description 1
- MLLLVRBYNSVZFT-UHFFFAOYSA-N 5-benzyl-4-phenyl-1h-pyrazol-3-amine Chemical compound C=1C=CC=CC=1C=1C(N)=NNC=1CC1=CC=CC=C1 MLLLVRBYNSVZFT-UHFFFAOYSA-N 0.000 description 1
- WRWVKKYBSJPYGJ-UHFFFAOYSA-N 7-benzyl-3,8-diphenylpyrazolo[5,1-d][1,2,3,5]tetrazin-4-one Chemical compound C(C1=CC=CC=C1)C1=NN2C(N=NN(C2=O)C2=CC=CC=C2)=C1C1=CC=CC=C1 WRWVKKYBSJPYGJ-UHFFFAOYSA-N 0.000 description 1
- LNDOWKNRUMBWFF-UHFFFAOYSA-N 7-methyl-3,8-diphenylpyrazolo[5,1-d][1,2,3,5]tetrazin-4-one Chemical compound CC1=NN2C(N=NN(C2=O)C2=CC=CC=C2)=C1C1=CC=CC=C1 LNDOWKNRUMBWFF-UHFFFAOYSA-N 0.000 description 1
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 1
- 239000005695 Ammonium acetate Substances 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 239000004471 Glycine Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical class O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- HXBPYFMVGFDZFT-UHFFFAOYSA-N allyl isocyanate Chemical compound C=CCN=C=O HXBPYFMVGFDZFT-UHFFFAOYSA-N 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229940043376 ammonium acetate Drugs 0.000 description 1
- 235000019257 ammonium acetate Nutrition 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001734 carboxylic acid salts Chemical class 0.000 description 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 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000002934 diuretic Substances 0.000 description 1
- 229940030606 diuretics Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical class CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000003630 growth substance Substances 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 150000004905 tetrazines Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
Classifications
-
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792932305 DE2932305A1 (de) | 1979-08-09 | 1979-08-09 | Azolo- eckige klammer auf 5,1-d eckige klammer zu - eckige klammer auf 1,2,3,5 eckige klammer zu -tetrazin-4-one und verfahren zur herstellung dieser verbindungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19792932305 DE2932305A1 (de) | 1979-08-09 | 1979-08-09 | Azolo- eckige klammer auf 5,1-d eckige klammer zu - eckige klammer auf 1,2,3,5 eckige klammer zu -tetrazin-4-one und verfahren zur herstellung dieser verbindungen |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2932305A1 true DE2932305A1 (de) | 1981-02-26 |
| DE2932305C2 DE2932305C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-03-22 |
Family
ID=6078036
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792932305 Granted DE2932305A1 (de) | 1979-08-09 | 1979-08-09 | Azolo- eckige klammer auf 5,1-d eckige klammer zu - eckige klammer auf 1,2,3,5 eckige klammer zu -tetrazin-4-one und verfahren zur herstellung dieser verbindungen |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2932305A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2511679A1 (fr) * | 1981-08-24 | 1983-02-25 | May & Baker Ltd | Nouvelles imidazotetrazinones, leur preparation et les medicaments qui les contiennent |
| FR2531958A1 (fr) * | 1982-08-17 | 1984-02-24 | May & Baker Ltd | Nouveaux derive |
| EP0127028A3 (en) * | 1983-05-24 | 1985-08-14 | Warner-Lambert Company | 3-haloethyl-4-oxopyrazolo (5,1-d)-1,2,3,5-tetrazine-8-carboxamide and process for their production and use |
| EP0252682A3 (en) * | 1986-07-02 | 1990-01-10 | May & Baker Limited | Tetrazines |
| US5260291A (en) * | 1981-08-24 | 1993-11-09 | Cancer Research Campaign Technology Limited | Tetrazine derivatives |
| CN1727340B (zh) * | 2004-07-29 | 2011-05-18 | 天津帝士力投资控股集团有限公司 | 一种替莫唑胺-8-羧酸酯及其组合物 |
-
1979
- 1979-08-09 DE DE19792932305 patent/DE2932305A1/de active Granted
Non-Patent Citations (2)
| Title |
|---|
| Bull. of the Chemical Society of Japan, 49, 1976, S.1339-1341 * |
| The Chemistry of Heterocyclic Compounds, Bd.33, Chemistry of 1,2,3-Triazines and 1,2,4-Triazines, Tetrazines and Pentazines, John Wiley and Sons, New York, 1978, S.165-167 * |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2511679A1 (fr) * | 1981-08-24 | 1983-02-25 | May & Baker Ltd | Nouvelles imidazotetrazinones, leur preparation et les medicaments qui les contiennent |
| DE3231255A1 (de) * | 1981-08-24 | 1983-03-03 | May & Baker Ltd., Dagenham, Essex | Tetrazin-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen |
| AT380256B (de) * | 1981-08-24 | 1986-05-12 | May & Baker Ltd | Verfahren zur herstellung eines neuen (3h)-imidazo-(5,1-d)-1,2,3,5-tetrazin-4-onderivats |
| US5260291A (en) * | 1981-08-24 | 1993-11-09 | Cancer Research Campaign Technology Limited | Tetrazine derivatives |
| FR2531958A1 (fr) * | 1982-08-17 | 1984-02-24 | May & Baker Ltd | Nouveaux derive |
| EP0127028A3 (en) * | 1983-05-24 | 1985-08-14 | Warner-Lambert Company | 3-haloethyl-4-oxopyrazolo (5,1-d)-1,2,3,5-tetrazine-8-carboxamide and process for their production and use |
| EP0252682A3 (en) * | 1986-07-02 | 1990-01-10 | May & Baker Limited | Tetrazines |
| CN1727340B (zh) * | 2004-07-29 | 2011-05-18 | 天津帝士力投资控股集团有限公司 | 一种替莫唑胺-8-羧酸酯及其组合物 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2932305C2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-03-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0042592A1 (de) | N-Heteroaryl-alkylendiamine, Verfahren zu ihrer Herstellung sowie ihre Verwendung | |
| DE2009020A1 (de) | Verfahren zur Herstellung von N-(1,1,1trisubstituierten)-Methylazolen | |
| DE69226590T2 (de) | Verfahren zur Herstellung von substituierten N-Aryl-1,2,4-Triazolopyrimidin-2-Sulfonamiden | |
| DE2321330A1 (de) | Azolyl-amidine, verfahren zu ihrer herstellung sowie ihre verwendung als herbizide | |
| DE2657578A1 (de) | Imidazolyl-oximaether | |
| EP0006540A1 (de) | N-Dichloracetyl-1,2,3,4-tetrahydro-chinaldin, Verfahren zu dessen Herstellung und dessen Verwendung zur Verhütung von Herbizidschäden an Kulturpflanzen sowie selektive herbizide Mittel auf Basis von N-Dichloracetyl-1,2,3,4-tetrahydro-chinaldin und herbizid wirksamen Acetaniliden oder Thiolcarbamaten | |
| DE2655009A1 (de) | Isoxazolderivate, verfahren zu ihrer herstellung und diese verbindungen enthaltende mittel | |
| DE2932305A1 (de) | Azolo- eckige klammer auf 5,1-d eckige klammer zu - eckige klammer auf 1,2,3,5 eckige klammer zu -tetrazin-4-one und verfahren zur herstellung dieser verbindungen | |
| DE2835157A1 (de) | Verfahren zur herstellung von n-substituierten alpha -halogenacetaniliden | |
| DE69216143T2 (de) | Prozess und 2-(Cyanoimino)-Quinazlin-Zwischenprodukte zur Herstellung von 6,7-Di(Chloro)-1,5-Di(Hydro)-Imidazo-[2,1-b]Quinazolin-2[3H]-on sowie Prozess zur Darstellung der 2-(Cyanoimino)Quinazolin | |
| EP0726258A1 (de) | Verfahren und neue Zwischenprodukte zur Herstellung von Triazolinonen | |
| EP0453885B1 (de) | Verfahren zur Herstellung aromatischer Amine | |
| EP0006542A2 (de) | Verwendung des N-Dichloracetyl-1,2,3,4-tetrahydroisochinolins als Gegenmittel zum Schutz von Kulturpflanzen vor Schädigungen durch herbizid-wirksame Acetanilide; die so erhaltenen Kombinationen und Verfahren zu deren Herstellung | |
| EP0003540B1 (de) | N-Azolylalkyl-aniline sowie Verfahren zu ihrer Herstellung | |
| DE4343595A1 (de) | Verfahren zur Herstellung von Sulfonylaminocarbonyltriazolinonen | |
| EP0572887B1 (de) | Verfahren zur Herstellung von naphtholischen 2-Äquivalentcyankupplern | |
| DE2933962A1 (de) | Verfahren zur herstellung von 4,5-dichlor-imidazolen. | |
| EP0023307A1 (de) | N-(Alpha-Chlorpropionyl)-1,2,3,4-tetrahydro-iso-chinolin, Verfahren zu dessen Herstellung und dessen Verwendung als Gegenmittel zum Schutz von Kulturpflanzen vor Schädigungen durch Herbizide | |
| EP0043024B1 (de) | Verfahren zur Herstellung von 5-Aminoisoxazolen | |
| EP0006541A2 (de) | Verwendung von N,N-Diallyl-dichloracetamid zur Verbesserung der Kulturpflanzen-Verträglichkeit von herbizid wirksamen Acetaniliden | |
| DE3879243T2 (de) | Pyrazolderivate, verfahren zu deren herstellung und herbizide, welche diese derivate als wirksubstanz enthalten. | |
| EP0004322A1 (de) | Isochinolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Herstellung von Arzneimitteln | |
| DE3612940A1 (de) | Verfahren zur herstellung von 1-aryl-5-aminopyrazolen | |
| DE2131788C3 (de) | Verfahren zur Herstellung von 7-Pyrazolylcumarinen | |
| DD150057A5 (de) | Verfahren zur herstellung von 2-aminopyrazinen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8127 | New person/name/address of the applicant |
Owner name: EGE, GUENTER, PROF. DR., 6900 HEIDELBERG, DE GILBE |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8320 | Willingness to grant licences declared (paragraph 23) | ||
| 8330 | Complete disclaimer |